CS Mastermind #83 Transcript: Seamless Handoffs: Eliminating Gaps in the Customer Journey

A customer’s journey begins the moment they enter your organization’s orbit. When handoffs between Sales, Onboarding, Support, and Customer Success are fragmented or inconsistent, customers feel the friction. Misaligned expectations, repeated questions, and disjointed communication create frustration, undermine trust, and slow down value realization. Seamless handoffs, on the other hand, create momentum, strengthen confidence, and set the foundation for a long-term partnership.

Smooth transitions require intentional design, cross-functional alignment, and operational discipline. Whether you're a CSM receiving new accounts or collaborating across internal teams, mastering the art of seamless handoffs ensures customers feel supported, understood, and guided from day one.

In this CS Mastermind session, hosted byAndrew Marks and Kristi Faltorusso, our panelists discussed:

• Pain points customers typically experience during handoffs

• Ensuring Sales sets accurate and realistic expectations

• Operationalizing handoff processes so they’re consistent, repeatable, and scalable

• Effective tools or systems for creating visibility across teams

• Maintaining strong customer momentum during the onboarding handoff

• Collaborating with Support to ensure ongoing, cohesive customer care

This webcast featured:

• David Ellin, Chief Customer Officer at Centric Leadership Strategies LLC

• Eleni Vorvis, Fractional VP of Customer Success at CoachEm

• McKayl Bergman, Customer Experience Professional

Top Takeaways:  

1. Broken handoffs are a symptom of misaligned organizational incentives, not individual department failures. Sales teams are rewarded for closing, Onboarding for speed, and Customer Success for retention, but no one is measured on the customer's experience across all of these touchpoints. Addressing that structural misalignment is the first step toward a truly seamless customer journey.

2. Institutional knowledge and metrics must live in a shared system. When critical account information is centralized and accessible, incoming team members can get up to speed quickly without forcing customers to repeat themselves. That continuity is what makes the relationship feel consistent, even as personnel changes over time.

3. Sales teams can be held accountable for information quality without disrupting deal velocity. Requiring a completed set of fields or questions before a deal moves to closed-won gives post-Sales teams the context they need from day one. That gate preserves momentum on both sides while closing one of the most common gaps in the customer journey.

4. AI tools are already helping Customer Success teams streamline the handoff process in practical ways. Call recording platforms and custom prompts can synthesize deal history, stakeholder context, and account details into a ready-to-use summary for the incoming CSM. This reduces ramp time and keeps the customer experience feeling continuous, even across team transitions.

5. Defining success in measurable terms should begin during the Sales process, not after the contract is signed. When Sales captures what the customer is trying to achieve and translates that to the post-Sales team, Customer Success professionals can begin the relationship already anchored to the right outcomes. 

6. Cross-functional collaboration cannot be reserved for leadership. Individual contributors across Customer Success, Sales, and Implementation need the autonomy and encouragement to resolve gaps directly with their peers. Building that culture of peer-level problem-solving removes friction at every stage of the customer journey.

Session Replay

Session Transcript

NOTE: The following transcript has been edited for clarity and content where necessary to improve readability.

Andrew Marks: Welcome everyone. And thanks for joining us. I'm Andrew Marks, co-founder of SuccessHACKER and architect to the SuccessCOACHING training program. Finally, this month, I've recovered from my sickness and my jet lag from being in Europe. And you're stuck with me again, not just with Kristi.

Thank you for joining us for the CS Mastermind, a monthly conversation designed for both Customer Success leaders and individual contributors. Whether you're leading a CS organization, managing accounts, supporting customers or sitting somewhere in between, our goal is simple, help you do work that actually matters.

Before we jump in, I want to flag two things quickly and Ashley will drop the links in the chat so you don't have to scramble to write anything down. First, if you've been looking for a structured guided path through Customer Success fundamentals, we just launched our CS Foundations Executive Education Certificate Program and partnership with the University of San Francisco School of Management.

I love this program. I've been doing it now for four or five years through their school of management. This is a fully coached experience. You're not going through it alone. It's me. I'm joining you every week for 10 weeks. The first live coaching call is next Thursday. So if you've been on the fence, now is the time. Use code USFCSF25 to save 25%.

And if you're looking for something, you can start at your own pace. Our CS Foundations training program is live and ready for you today. This is something that we released the second half last year, only offered it to our team subscribers. It's now available for individuals. 18 courses covering the full customer lifecycle design to take you from a good CSM to a truly strategic one.

There's also an optional integrated exercise path where each exercise builds on the last, culminating in a capstone project using our fictional DigiSoft vendor and book of business. I spent a lot of time last year putting this thing together, really excited about it. You can use that fictitious vendor for both our CS foundations and our value-based selling program. Use code CSF20 to save 20%.

Okay, enough of the commercial stuff. Joining me as always is my co-host, Kristi Faltorusso. At this point, many of you probably know Kristi better than you know me. And honestly, after holding things down on her own more than a few times last year, as well as last month, she's probably wondering why we're even bothering to add me back. But one of our goals this year is to actually be in the same virtual room together more often. So you'll be seeing a lot more of both of us going forward. Kristi, great to be back alongside you. Try not to make me look too bad. Okay?

Kristi Faltorusso: I will do my best.

Andrew Marks: I appreciate that. A few quick housekeeping notes before we begin. This session is being recorded and the replay and transcript will be shared next week. Please use the Q&A feature for questions. The most upvoted ones will get priority. And use the chat for commentary and reactions. So commentary and reactions in chat, questions in Q&A. LinkedIn Live viewers, you can post questions directly in the comments which will be relayed to us.

Now, I'm excited to introduce today's panel. As always, I'll let our guests introduce themselves to y'all in alphabetical order so you can hear directly about their backgrounds and perspectives. Let's start with David.

David Ellin: Hi, everybody. My name is David Ellin. I'm from Atlanta, Georgia. I saw a couple people from Atlanta and Douglasville, so welcome. I'm the Chief Customer Officer of Centric Leadership Strategies and a Senior ustomer success Consultant and Revenue Architect with Winning by Design. I've worked with hundreds of companies designing go-to-market strategies, customer journeys, playbooks, and more. I'm also a certified executive leadership development coach. In my last corporate role, I was head of CS for a global B2B division of a Fortune 500 company with 1.2 billion in revenue.

Personally, I'm an avid reader. I'm a huge pickleball player. I love building Expert Lego sets. I have them all over my house. My wife hates me. The Titanic-

Andrew Marks: I was going to say, that's a Lego set back there. I love that.

Kristi Faltorusso: Yeah, that's a big thing.

Andrew Marks: That's awesome.

Kristi Faltorusso: Do you have an entire room or floor of your house dedicated to that?

David Ellin: Largest Lego set ever made.

Andrew Marks: Nice.

David Ellin: No, I have them all over the place. I am passionate about customer centricity and all that goes along with a deep focus on driving customer outcomes. I'm very active in the Atlanta Customer Success community, and I'm very happy to be with you guys today.

Andrew Marks: See that, David, right there?

David Ellin: Yeah.

Andrew Marks: That's Lego Yoda.

David Ellin: Is that Star Wars?

Andrew Marks: My daughter made that for me.

David Ellin: Nice.

Andrew Marks: We got a big Lego household here.

Kristi Faltorusso: Yeah, same.

David Ellin: Yeah.

Andrew Marks: Awesome. Eleni, you're next.

Eleni Vorvis: Thank you. Hi everybody, Eleni Vorvis. I'm based in Cambridge, Massachusetts, and I've been in go-to-market roles for just a little over 20 years. I started my career off in sales, but transitioned over to the success world. I found my people in my community. I'm currently the Fractional Vice President of Customer Success for CoachEm, and I do consulting and workshops for CSM teams as well. I know many of them are making the transition from just focusing on adoption to owning commercial responsibility, retention, and expansion.

And in many cases, they don't have the skills necessary because they've never done the job before. And we spend a lot of money and time on supporting Sales teams, and I feel CS teams need that training as well. So I'm happy to see there's definitely been a shift, and that's a passion of mine to help to enable these future leaders.

In my personal time, I love to work out. I began working with a trainer almost four years ago, and now I'm proud to say I enjoy deadlifting and doing other strength training, and barre and Pilates classes are part of my routine as well. And I'm definitely a big foodie, so if you're ever in the Boston area, I keep a list of the latest new restaurant openings and I can rattle off recommendations.

Andrew Marks: Like I mentioned during our pre-call, Boston's one of my favorite areas of the country, and I love the food scene there. So I may take you up on that next time around.

Kristi Faltorusso: She does a pretty good list of New York too, I'm not going to lie.

Andrew Marks: I don't know, New York can be-

Kristi Faltorusso: I don't think she's limited to Boston. It might be her longest list, but it's not her only.

Andrew Marks: Yeah, New York can be difficult.

Kristi Faltorusso: You can be difficult.

Andrew Marks: Yes, I know I can be. Yes.

Kristi Faltorusso: All right, let's do our last guest.

Andrew Marks: Yeah. So last but not least, McKayl.

McKayl Bergman: I love this conversation. Hi, McKayl Bergman. Most recently Director or Senior Director of Customer Experience at Griffin AI, which is based in Boston and where I started my Google list for my Boston restaurants. So I'll have to hit you up, Eleni. I have been in a variety of different Customer Success roles and leadership positions in every flavor of Customer Success, from the seed stage startups to Series A, B, C, D, E, all the way across the board and companies of all sorts, and I enjoy variety.

So my thrills are from all kinds of growth transformation projects. Give me your sticky, complicated, tough situations, and those are what I enjoy most. In my personal time now, I am currently on sabbatical. It's magical and lovely, and I recommend it to most people. And I am enjoying being in touch with the CS community while I enjoy revitalizing my life. I've recently moved from Utah to Portland and really loving the Pacific Northwest.

Andrew Marks: Awesome. I love that area. As I mentioned, my son's up right across the river from you in Vancouver, so I get up there often to see him. And Kristi is like my work wife. So anyways.

McKayl Bergman: Does Kristi need any introduction?

Andrew Marks: Yeah, Kristi-

Kristi Faltorusso: I'm just here to babysit Andrew and make sure he does his job and doesn't mess this conversation up.

Andrew Marks: Yeah, I'm prone to that. That's fine. She keeps me honest. All right. Well, thank you all for being here and for making time to share your experiences with this community.

I want to start today with a provocation, and I want you to tell me where I'm wrong. We talk about broken handoffs like they're accidents, like somebody dropped the ball, forgot to send the email, missed the meeting. But what if handoffs fail not because people aren't trying hard enough, but because the system is actually working exactly as it was designed?

Think about it, average tenure in a critical customer facing role is somewhere between 18 to 24 months. The customer you're trying to keep for five or more years will be touched by dozens of people across sales, onboarding, support, and CS, most of whom will be gone before that customer renews a second time. Every one of those teams has its own incentives, its own tools, its own definition of success, and nobody at the top is being measured on whether those things point in the same direction.

So the handoff breaks, not because of the handoff, because sales was optimized to close, onboarding was optimized for speed, CS was optimized for retention and support was optimized to resolve tickets. Nobody was optimized for the customer's experience of all four. Handoffs are a symptom, misaligned incentives are a symptom, sales lies is a symptom. The disease? That we built organizations around departmental convenience and called it a customer journey. And a world where the cost of acquiring a new customer routinely exceeds the revenue from their first year and where the math only works if they stay long enough to pay back that investment several times over, we can't afford to keep treating symptoms.

So let me ask the panel. If the system is producing exactly the results it was designed to produce, what actually has to change?

McKayl Bergman: I'm happy to kick this off. So it's an interesting topic. This one's dear to my heart. So I think it's true that everybody knows that we don't stay in our roles forever for our lifetime, gone are those days. And so our customers will always experience fragmentation within our organization as we change. It's inevitable that they will miss somebody at some point and have to say goodbye to someone that they've grown to know. So how do we continue to perceive continuity and consistency when there is rarely continuity nor consistency?

I think that the critical function here is understanding what does our customer need to experience for themselves regardless of who delivers it? And then make who delivers it a secondary question and who records it and where they record it, a tertiary question. So if we focus on our customer's understanding of their own particular working environment, their wishlist, the complications they haven't been able to challenge for several years in their own organizations, then we can focus on what they need to be able to achieve rather than who on our site delivers it.

So I'm going to start there. Anyone else want to chime in or contradict?

David Ellin: I think both the system and the processes need to change, including internal alignment across the customer journey, especially a customer journey that's customer-centric in terms of mindset. Today, most companies don't have departments that are dependent upon each other. Or they do have departments that are dependent upon each other, and that's a very reactive thing. I'd like to see departments that support each other and set each other up for success. And that's proactive, and that's a completely different mindset in an organization.

Andrew Marks: Eleni, you got anything to add?

Eleni Vorvis: Yeah. I agree with both thoughts. I think the other thing too is asking the questions around how is each team incentivized and creating common metrics instead of optimizing for each of the departments and the roles and responsibilities. If we're all tasked with doing different things, then it doesn't matter how much we optimize the journey for the experience of the customer. We're still going to run into challenges if we are making moves or focusing on goals that then contradict what we want the customer to experience and the journey that we want them to go through.

So I think leadership, having those conversations and being very transparent about those metrics and having those shared goals, then everybody understands how what they do day to day, impacts the customer long-term. Because everybody plays a role within the go-to-market motion on making a Customer Successful to deliver value and to achieve business outcomes.

Andrew Marks: So I was going down that path because we've been actually focused on the concept of the revenue team. What is your definition of the revenue team when you say everybody plays a role?

Eleni Vorvis: Sure.

Andrew Marks: I mean, you could say the entire company, but let's focus on the particular groups that really need to work well together. I would love to hear your list and see if it matches up with my list.

Eleni Vorvis: Sure. Marketing, sales, Customer Success, and product. I think from the CS lens, those are all departments that we work with.

Andrew Marks: Yes.

Eleni Vorvis: Engineering also plays a role. And if engineering and product are not aligned and engineering is not understanding what the customer is looking for, their experience, their outcomes, then it doesn't matter what the rest of the go-to-market teams say. If the engineering team is not building a product that will deliver an outcome, it doesn't matter if it looks good, if you have a flashy UI, if you believe in your features. If no one is using it, then what's the point? So we need to communicate that information and help them understand the work that they do, why it's so important and how it does make an impact.

Andrew Marks: Hundred percent. And that was the list. That was my list exactly. It's good to get that validation because we believe that everybody needs to have that customer-focused mindset, especially those four components. That is the revenue team.

Eleni Vorvis: Yeah. And one more thing just to add because Customer Success, the flavor is different at each company. So I'm talking about all of the teams that come after sales, the post-sales.

Andrew Marks: Post-sales.

Eleni Vorvis: So implementation that could sit as professional services, education, support, Customer Success management.

Andrew Marks: Project management, anybody who's involved in helping the customer achieve what they're trying to achieve.

McKayl Bergman: And I want to chime in and add to that too. Every company is different. And I think there's even companies where the legal team or the billing team have a significant part to play in what the customer's experience is in working with us. If you're working with your Fortune 100 companies, Fortune 50 companies, your contracts could be 40 pages long, and those legal terms matter and the legal engagements matter. So it really becomes everybody, which is in a way its own obvious thing. Of course it's everybody, it's the whole company. The whole company produces what we're selling to our clients. So-

David Ellin: And-

McKayl Bergman: Go ahead.

David Ellin: In a lot of organizations, they don't consider support as part of CS, they consider support separately, often reporting up to the chief operating officer, and sometimes account management who's on that post-sale team also may report into sales and not be considered. So I'd add those to the list as well.

McKayl Bergman: Agreed, totally agree. And so in this way, we end up hitting every department in the company. So there's an interesting corollary or story here really. I think as a customer, if we think through what are all of the things that we as CS ask other departments to do on our customer's behalf and what do all of these other departments ask us to do on our customer's behalf or for permission or access to talk to a customer, it's easily possible that a customer could interact with 10 different people, 15 different people, maybe even 20 different people, depending on your company size and the product complexity that you're serving.

And so with all of those people in the kitchen and knowing that we can't generalize to one, we will always have handoffs, always. So an interesting thing I think that smooths out those handoffs is when instead of looking at each individual challenge or problem or project that we have in a company as, all right, let's find the list of 100 customers who apply to this problem. When we keep the pulse on a regular basis, let's say a monthly check-in, for example, of a series of customers understanding in each of these departmental categories, what is the customer's desired objective? What are they trying to achieve and what experience is considered appropriate? And what experiences detract from their perception of our company?

If we speak with our customers directly, for example, I've had these conversations where they'll call out errors on the marketing pages. Or they will call out clauses in their contracts that are cumbersome and frustrating. Or they'll call out a system with the billing team that doesn't work well for them. Or they'll call out something in the product that doesn't work or something that doesn't work in their CS engagements. So it's important to look at it from one customer's perspective, start there sometimes rather than our consistent approaches, which tend to be, "Here's my spreadsheet of customers and let's aggregate at the top."

Andrew Marks: That's an incredibly inside out thinking approach. You need to be thinking outside in. It's one of the first things that we teach right out of the gate, thinking like a customer. Kristi, you've been unusually quiet.

Kristi Faltorusso: Not unusually quiet. I think that I'm aligned generally with what everyone's saying. I think, McKayl, listen, I think that what you're saying is 100% accurate. I think it becomes a slippery slope when we try to dial these things in. So if it's for everyone, it's for no one. So I think it's just trying to figure out what are the things that we're trying to optimize for intentionally-

McKayl Bergman: Completely.

Kristi Faltorusso: ... to make sure these things go as smoothly as possible. And I think it's what we're going to tackle today. So that would be my only additional comment to this part, Andrew, but I've got lots to say as we continue on. So ask the next question, sir.

Andrew Marks: Yes, ma'am. All right. Uh-oh, I'm in trouble. That means I'm going to get talked to after this. All right. So let's start with the tenure problem because I think it's underappreciated. If the average person in a critical customer-facing role is gone in 18 months and you're trying to retain a customer for five or more years, what does that mean for how you build systems, documentation, institutional knowledge? How do you make the relationship bigger than any one person? We talk all day about, "Oh, we got to get people the right mindset." How do you do that? Where does that start?

Eleni Vorvis: I think it starts-

McKayl Bergman: Can I-

Eleni Vorvis: Oh.

McKayl Bergman: Go ahead, Eleni.

Andrew Marks: Go ahead, Eleni.

Eleni Vorvis: I think it starts with planting the seed during the sales process on that it takes a village to work with a customer. And while there may be one person who helps to herd the cats and maybe facilitate the conversation, just setting up the expectation who they're going to interact with along their journey and why it is important. We ask of them to have a project team ready, for there to be an executive sponsor, the champion, the end users, the IT lead. And then on our end, we're talking about the individuals they're going to interact with.

So I think if we let them know that it is a team approach and here are the various ways in which people will become involved and will come in and out of the process, then the customer's understanding, okay, I have this team that's working behind the scenes. It may be that Eleni's my main point of contact, but if I need something outside of her realm of expertise, she's going to bring people in. I think we're used to doing that in Customer Success.

I think the other thing is our customers probably also face a tenure problem depending on the industry that they're in. So why don't we just be more honest about the fact that you may be a customer longer than somebody is in the seat or they're getting promoted, right? So there will be change that happens, but what matters most is keeping that institutional knowledge.

So the other point I wanted to quickly make is just having a way for everybody to agree on where are we going to have information about this customer, the necessary points that are relevant, that way we don't have to keep asking them the same question over and over again. I know that this really annoys customers. There may be updates to that information as their business changes, but the last thing a customer wants to hear is like, "Okay, so tell me how you're using the product? Talk to me about all the things and why you bought, et cetera." They're going to think to themselves, "Well, this person has no clue what they're doing. They did no prep work and the company as a whole doesn't have a way for sharing information."

So I think having that system set up will also just help. And it doesn't need to be anything fancy. If you're a small company, just start with one repository. And then as you grow, you can find ways to automate and share that information, but it can't exist-

Andrew Marks: If you're a small company, you can use Google Docs and put all the notes in there and just go through the ... And these days you have no excuse because you can feed that into Claude and say, "Provide me a summary and make sure it stays within these boundaries and yada, yada, yada." There's no excuse to show up unprepared. If you are asking customer questions that they've already answered, you're doing it wrong, period.

Eleni Vorvis: Absolutely.

Andrew Marks: Stop it now.

Eleni Vorvis: Yes.

David Ellin: Yeah.

Andrew Marks: Okay? Stop it.

Eleni Vorvis: And it can't be in your brain. It can't be in the CSM's brain or in the CSM's OneNote on their computer or in their physical notebook because there are people that just like to take notes in a notebook. That is not going to be great because when that person leaves, they're not going to spend the time, let me type up all my notes, and share that information from you. So from the beginning, it's setting up that expectation internally on here's what we're going to do, where the information exists, and then how do we keep it fresh? So depending on the systems that we use, we make sure that that information gets updated over time.

Andrew Marks: And the vast majority of technology that we're using these days to work with or interact with others and our customers is Zoom and it's recorded and can transcribe and there's no excuse if you are showing up. I'm going to make this real clear. You're showing up and asking the same questions, you're doing it wrong. Stop immediately, no excuse.

David Ellin: Yeah, that's where I was going to go with it, is you have to build systems that first have a single point of truth and everybody that has to have access to it should have access to it. I have worked with some organizations where the single point of truth is the CRM, but only the sales team has access to the CRM. So things are getting written in the CRM and the CSM is waiting for information to be transferred from the CRM to the CSP.

Andrew Marks: You know why that is, David?

David Ellin: Maybe it happens. Maybe it goes to Tableau.

Andrew Marks: You know why that it is? It's because they're too cheap. They don't want to buy a license for the CSM.

David Ellin: Yeah.

Andrew Marks: Even though the CS team is responsible for 65 to 80% of the lifetime revenue of the company, they don't want to spend the money for the seat.

Kristi Faltorusso: Listen, Andrew, even when they do though, let's be honest, Salesforce also has permissions.

Andrew Marks: Yeah.

Kristi Faltorusso: Even if users across the org all have a license, not every license is treated equal. You log in and I see something completely different than the next person. So there also needs to be some continuity there.

Andrew Marks: Yep.

Eleni Vorvis: Yes, and I think optimizing too for what fields we are using and are those fields that are required? And so when the CRM admin or individual that's responsible is looking to build out that structure, don't forget about Customer Success. It's not an afterthought. It's not a project you'll take on when you have time. It needs to be a holistic look at, here's all the possible information we want to gather about a customer over time.

And I think when you make the case that from that information, then marketing can figure out who is a reference-able customer, who do we want to invite to a webinar? If there's a success story or a use case that's going really well with a set of customers, then sales gets that information. So it's like we're trying to make everybody's lives easier.

And there is more ROI and value to giving the access and setting up the process versus trying to share information via email and on Slack because those are great ways to communicate, but not to house institutional knowledge. It needs to be somewhere that can then be pushed out to other systems or easily accessible by those that need it.

Kristi Faltorusso: And I think we could easily go down the governance rabbit hole. I want to get us back on track onto the conversation because I think we can all agree here, most systems don't have the proper governance that they need in order for us to have any level of efficiency. But one thing I will go back to your question here, Andrew, with the tenure.

The biggest issue here is consistency and continuity, and those two things don't exist in many organizations. I have been a customer of organizations where I've had multiple CSMs, multiple stakeholders, and I did not have a consistent experience from one to the other. Same role, same title, same responsibilities, completely fragmented experience working with these different people. There needs to be an intentional design to create consistency.

And the continuity doesn't mean one person, right? It needs to be that continuity in the customer's communication to us and our ability to manage through that. Going back to things like omnichannel versus a multichannel experience. I don't care that you could talk to me multiple places. I want to make sure that my data and what is being communicated is managed through all those mediums effectively. So those are the things that are going to create, I think, more disruption, and those are things that we can definitely break down here.

McKayl Bergman: And I think there's a really interesting tieback, both Kristi and Eleni, back to incentives here. Very, very rarely are we having discussions with other departments about their own incentives outside of our post-sales org. Most commonly, I'm discussing incentives between sales, marketing, and CS. Those are the folks that I'm discussing and curious about their incentives and their structures.

But across the organization, if we need documentation, that's really what we're talking about, documentation consistently coming from each department, be that legal, marketing, sales, Customer Success, account management, implementation, support, name all of them, then it needs to be a goal that is understood at the top level and understood that it needs to be incentivized.

Otherwise, it is so easy for every single one of us to say, "I've got five back-to-back meetings today. I need to prep for three of those to be customer calls. I don't have time to go streamline or clean up or organize or check that everything I've written down is going to be done. I'll do it later tonight or I'll do it tomorrow morning." We're all human. We all experience that even though we know it's important.

So it helps to have incentives across the company align, not just in CS, but in each department that those notes matter. They truly matter because Kristi, you could get hit by a bus. I don't know why I'm saying that.

Kristi Faltorusso: I'm winning the lotto. I'm not getting hit by a bus. I'm winning the lotto. If I leave, it's because I'm rich and I don't need anybody.

McKayl Bergman: Right, you could win the lotto. Any one of us could do that.

Andrew Marks: If a bus hit her, I wouldn't want to see the bus afterwards.

David Ellin: If she wins the lotto, she's buying the bus that's going to hit Andrew.

McKayl Bergman: There you go.

Kristi Faltorusso: Whoa. Whoa, this went dark.

Andrew Marks: Wow. Damn.

Kristi Faltorusso: I never said that, Andrew.

Andrew Marks: Wow. No wonder you got the Titanic behind you. That's an interesting segue, McKayl, to my next question, which was on incentives. Every department has incentives that made sense when someone designed them. Sales rewards closing, onboarding rewards speed, CS rewards retention, but those incentives were designed in isolation. When you look across the full customer journey, where do those incentives actively work against each other and who in the organization even has the authority to fix that?

Back in the day when I launched one of the first Customer Success teams outside of Salesforce at Intacct, my CEO at the time, who I know you might not believe this, but I butted heads with, one of the things that I really respected him doing was he made part of every single person's comp plan, from him all the way down to the guy who sat at the front desk, the receptionist, everybody had a piece of their comp plan tied to NPS. What was the NPS score?

McKayl Bergman: incentives, right?

Andrew Marks: I love that. But to your point, there needs to be incentives that drive a positive customer experience. And outside of Customer Success, we seem to be the only ones that are stuck with that. Hey, you have to drive retention and expansion. Well, what about all these other people that are part of that?

David Ellin: Yeah, incentives are a funny thing because typically they're siloed to a department and ultimately it's the senior leadership team that has to align on how people get paid. And I think where they miss the boat is they don't align incentives around common organizational strategic objectives. So for example, if a strategic objective is new logo sales and it's not retention or it's not expansion, and the sales rep is responsible for both new logo acquisition and expansion, if they get 60% commission for new logo and they get 30% commission for expansion, you're never going to see any expansion. And the CS team is going to be left hanging in the lurch about expanding customers and they're not getting paid for it.

So incentives have to go across departmental lines and they have to be aligned to high level strategic goals. What is it do we want to do? And we're all in it together to do those things and incentives should reinforce that.

Andrew Marks: How about the variable component? How about 50% of your variable component, if you were part of that revenue team that Eleni mentioned, which I 100% agree with, 50% of your variable component is tied to retention? How would that change things? Incentives drive behavior.

David Ellin: People would look at their jobs differently, that's for sure.

Andrew Marks: Yep. This is a fight that I've been fighting for years. Everything changed in technology when we moved from on-prem to the cloud, but the incentive structure didn't. The delivery did, the development process did, the sales process did, the marketing did. The one thing that didn't change was incentives, except for the Customer Success folks, except for the post-sales team. The post-sales team got stuck with all the risk and really typically a cap on the reward.

McKayl Bergman: I think it's a really interesting thought experiment to think through, if you think through how to systematize those incentives even. Let's take a really common scenario. You've got a team of CSMs and they tell you as their leader that they are constantly bogged down and chasing information. If we were in a classroom and everybody raised their hands, every hand in this room would be up. We've all experienced that.

And if those CSMs can't find the information they need in product documentation or they can't find the information that they need about the contract so they can't find the information they need to solve problems, then we get into handoff problems and we get into time-wasting.

So what if, for example, there were incentives that said, "We have a system to track every time a CSM or a post-sale person needs information from any department, from any kind of information for this customer. What if that was a ticket? We could count how many times we were lacking product documentation. If it was a ticket, we could count how many times we went to our CRM and sales hadn't entered in some information, whether CSMs hadn't entered information. It'd be very enlightening and very interesting to see how often we do experience a gap on a day-to-day basis. It'd be a way to create a system behind these incentives for documentation and to track improvement over time. But anyway, that's maybe a rabbit hole.

Andrew Marks: I think it's a huge rabbit hole, but I agree with you. The last thing I want to go down, and it's one of the reasons I started this company was because I didn't want to implement systems anymore.

McKayl Bergman: And here you are, still talking about implementing systems.

Andrew Marks: Yeah, exactly. Anybody else have input on the incentives angle?

Eleni Vorvis: Yeah. I think there can be a misunderstanding of the outcome that customers want to achieve. I think we focus so much internally, particularly from a product perspective on utilization, like how many times are people logging in? We've got this new feature and we want customers to beta test it or to utilize it. We're speaking our own internal language of metrics that don't mean much to the customer and they mean zero to the executive sponsor. That's not the language that we should be speaking.

And I think getting every department to speak that language and understand, okay, for this set of customers, here were their pain points. Here's how they're getting an outcome. Why don't we create an incentive for getting X percentage of customers to hit an outcome? Because if they hit their outcome and there's an ROI, they're more likely to renew, they're more likely to expand.

But I think we just focus, in other departments, so much on like, we're building these new features and we know this is going to be a great product to use and we want them to renew. But in order for them to renew, it starts off on understanding the customer's business and speaking that language. So we need to articulate that across departments. And wouldn't it be great if we spoke the language of the customer in all of those areas?

Andrew Marks: It's a huge issue. We're getting ready to release a report hopefully in the next couple of weeks that just is going to be very eye-opening to people on how much their efforts to keep customers are failing and that it really is a bigger issue than just something that Customer Success should be dealing with.

David Ellin: And incentives don't always need to be tied to NRR or GRR. I worked with a company not too long ago where the incentives were completely screwed up. Sales was paid on closing a deal. That's all they cared about. And they would sell anything and throw it over the wall to onboarding and Customer Success. And so, one of the things we did was we created an ideal customer profile and we set a metric that 90% of all new business that comes in has to be in confirmation to the ICP. And if it's not, the sales rep gets dis-incented for that.

And so every month or every quarter, I don't remember what they decided to do, they would do a review of all of the new business that those reps brought in and how they conformed to the ICP. And they set metrics around that, and then they tied an incentive to it. Changed behavior pretty quickly.

Andrew Marks: Yeah, of course it does. Just a reminder folks, we will be getting to questions here in the next few minutes. So if you have questions, please use the Q&A button, or if you have something you want the panel to weigh in on, use the Q&A button, please.

Let's see. We talk about alignment a lot in this industry, but I think we're often too polite about what misalignment actually looks like in practice. Misaligned by degrees, small disconnects that seem manageable still puts the train off the tracks eventually. Anybody have an example of what slow drift looks like before it becomes a crisis?

McKayl Bergman: I'll give you an example here. I think it's very common for us to have a goal that we want to achieve as an organization, and we pass it down to our team members, and we then filter it through a variety of different people's words and phrases and explanations and understandings. Sometimes those simple misunderstandings of a concept or of a directive can really get us on different pages. I'm thinking of a pricing launch gone wrong in my recent history where people-

Andrew Marks: It's like the game telephone, right?

McKayl Bergman: Exactly.

Andrew Marks: Where you say something at the beginning and at the end, it's completely different. Happens all the time.

McKayl Bergman: Yep. Take a product launch or a product roadmap discussion, this will be launched in Q3, and then that changes to soon. And then those don't all get updated for everybody. And so some folks in sales think it's end Q3. Some people think it's Q4. Some people say it's two weeks from now. It's very easy for small phrases and small things to create misunderstandings. And it really reinforces how important it is for us to both document and to publicly make sure we are course correcting when information changes.

So David, you've made an interesting comment about incentives and how they're not the end all, be all. But how often do we as leaders or as groups make our lists of the behaviors that are happening in the org, small and medium and large, just writing them all down to think through how can we incentivize the correct behavior, whether it's a monetary incentive or not? Maybe it's a cultural change we can change. Maybe it's a way of leading a meeting differently. There's a lot of different little things we can do to help close those small misalignments that get us too far away down the track.

Andrew Marks: Yes, Kristi.

Kristi Faltorusso: Can I jump in? Can I jump in? All right, so I've got something to add on that.

Andrew Marks: She's got something. She's got something.

Kristi Faltorusso: I got something. So something to add on that is, I think something else that we see as a breakdown is that oftentimes teams elevate those issues, concerns, or gaps to their leadership team instead of working directly with their peers to get those things resolved. When I was leading CS teams, I would have my CSMs come to me with their problems instead of going directly to their counterparts to go have an honest conversation of where something may have been broken.

And so you need to be able to facilitate that cross-functional collaboration at all levels. It can't just be at the most senior levels. And people need to not be scared or whatever their reason is preventing that. They have to be able to work together at all levels to go and resolve that.

Andrew Marks: Yeah, but Kristi, I get that, and this was the next question on the list, but there's a very politically tricky part in understanding why each department behaves the way they do and it requires you to look at their incentives honestly and without judgment. And the problem is, especially in sales, and Eleni, you can attest to this whether you agree or disagree, how do you have that conversation, especially when one of those departments is sales and that conversation can easily turn into a blame session? You got people who are-

Kristi Faltorusso: I had a part two. I had a part two. I wasn't done.

David Ellin: Can I-

Andrew Marks: Go on.

David Ellin: Before you go to part two, can I comment on your part one?

Kristi Faltorusso: No, not yet.

McKayl Bergman: No, no, yeah?

David Ellin: Okay, so the part one is I completely agree with you.

Kristi Faltorusso: Wait. No, I said no, not yet.

David Ellin: Oh, no, not yet. All right. Okay.

Andrew Marks: Nobody's listening to Kristi. Come on.

David Ellin: I reserve the right-

Kristi Faltorusso: I get yelled at for not speaking. I get yelled at for speaking. I don't know. I'm lost here.

Andrew Marks: I'm telling you, this Pomeranian thing is really turning into a-

Kristi Faltorusso: [inaudible 00: 39: 26] important context-

Andrew Marks: Sorry, go ahead.

Kristi Faltorusso: ... is because I wanted to give an example to follow McKayl's example is that in organizations, let's do this, let's play this one out, there is required information, right? So Customer Success teams or post initial sales teams will often need certain information to successfully move that customer through whatever journey it is, but sales stop selling once they've sold.

So if a customer is in a sales process and they say, second call, "You know what? Just send me the contract. I'm ready to sign," sales is not going to continue to have the eight following discovery calls or alignment sessions that are required as part of the information gathering process that fulfills our needs because now the deal is closed. They're going to send the paperwork, they're going to have that signed, and now that will continue to move through the process. I don't know a company that will say, "Let's slow down this sales process. Let's go and have more conversations after the customer has already committed to the close."

And so the reason I bring that up is now we've got this misalignment. We've got additional gaps in information and we don't have the things necessary to continue to fulfill the experience for the customer. That is an organizational intentional design that is creating and facilitating these gaps. But tell me, Andrew, do you find organizations that are going to require the sales team to keep selling once it's sold?

Andrew Marks: So we actually solved that exact problem at Intacct.

Kristi Faltorusso: Go.

Andrew Marks: I sat down with my sales counterpart, Kathy Lord, great woman, still keep in touch with her, just saw her last year, and I said, "Listen, there's stuff that we need to be effective in the initial transition and the onboarding process." I said, "I don't want to slow down your sales process because I understand how you are incented. You are incented to capture as much revenue, turn as many deals as possible. I get that."

"So what I want to do is I want to put a gate right before the sales rep, the customer's already signed, they cannot set the deal to closed won and therefore get paid for it until they've answered this list of 12 questions that we need to be properly educated on where the customer is at." We made most of them multiple choice, multiple select. There were a few freeform texts. We told them, "You got to attach the value prop here, what have you."

And talk about incentives driving behavior. Overnight, my team had so much more information in front of them before reaching out to that customer to have that initial discovery call. It wasn't asking the same questions over. It was validating, here's what we understand.

Kristi Faltorusso: Why not whomever the next person is, I won't say customer, it could be implementation, CS, onboard, I don't care who it is. Why not have that person be a part of that conversation so that we don't have another need to transfer information?

Because I don't disagree with what you're saying and I had the same gates. And Salesforce is fun like that, you can require information so that things don't actually close in systems. But if we're talking about handoffs and that conversation is only happening after a contract is signed anyway, why exclusively leave that discussion with the salesperson instead of bringing that in so that more information is flowing through the org?

Andrew Marks: And in certain situations and in certain size customers, especially enterprise customers, hundred percent agree with you. As a matter of fact, the key members of the post-sales team should be riding along in the latter stages of the deal before it's even done. So they've built up an understanding of the customer, they have connected with them, they've started to establish a relationship, hundred percent.

But the reality is that I can handle that if I've got five large accounts, but if I got 50, 75, 100 accounts that I'm babysitting, it doesn't scale. That approach does not scale. So you got to have something to address the 80%, not the 20. Eleni, sorry, go ahead.

Eleni Vorvis: I've got a lot of thoughts about this, but if you're closing a customer and you can't even answer some fundamental questions that then makes them not your ICP, do we even want to accept that deal? I think this goes back to your culture comment, Kristi. And if we're not creating a culture in which people can speak up when they're seeing that something is not working correctly and they work with their peers to try to figure it out, where people are not transparent about how they're incentivized and why are they moving quickly? And also maybe us explaining to the prospect, here's why we need this information. That way when we get started, you have the right people.

Because I have a feeling in that example that you gave, they probably don't even have their project team and the expectation setting set up. And it's not scalable to always have a CS person, but I think it goes back to what's the culture? And we need people to be able to problem solve at that individual contributor level and then bring up those trends.

And Andrew, you asked the, well, it becomes a blame session. It doesn't if you come with data and you're not going to say, "You did this thing wrong, and I'm going to start with a laundry list of the ways that your team doesn't know what they're doing." It's you come to them with a specific example, you build a relationship of where I want to help you. I know how you're being incentivized. I don't want to get in the way of you making money, but I think we all need to be aligned with a customer closing that's going to renew.

And I think you can hold the sales team responsible for that, that they are on the hook until that customer renews or they're on the hook for them to receive the outcome. And there's some organizations that are forward-thinking and are making that happen or they're holding back commission payment until there is a successful transition and there is the kickoff call and things kind of go off.

Andrew Marks: Hundred percent.

Eleni Vorvis: Right? I think it's up to leadership to align on that, sales and CS. And if you roll up under the same leader, it may be a little bit easier. If you don't, then there might be some clashing. But if you're not setting the tone for your team, then it kind of doesn't matter what the CSMs try to do. They're going to be spinning their wheels and they're never going to be effective. Or they're going to say, "What's the point of bubbling this up anyways? Nobody cares. We're trying to fix things and they're slapping our hands saying, 'Don't do that. That's not the way we want to do things here.'"

Andrew Marks: Early in my career, I know you might not believe this, Kristi, I was very confrontational and I butted-

Kristi Faltorusso: Oh, I'm glad you're not anymore.

Andrew Marks: I looked at the sales team as they were the enemy, and then I took on that. I'm like, "Wait a minute, let's employ empathy here. Let's understand their perspective." This is what we teach also in some of our content, hey, you need to think about it from their perspective and approach this not as a blame game, but as a, here, this is a learning process for everybody.

Eleni Vorvis: And you stumble. I mean, I've had that too where I made assumptions about a sales rep that I was working with on an actual customer renewal and he was trying to do one thing and I was trying to do another. And in my mind, I created this narrative that he was trying to undermine me, he had no respect for the Customer Success team. And it's because I didn't understand how he was being paid. And then I just thought to myself, "Well, there must be another reason why he's acting this way, the behavior. It's not just out of the blue. He doesn't really know me so how could he want to not make me successful?"

And then I just asked him, I'm like, "I feel like maybe you're doing this because of how you're getting paid and here's how I'm getting paid on this." And then we realized that there wasn't an alignment. And then that created conversations with our direct managers and then that kind of bubbled up and we realized we can't be competing against each other because then the customer also senses one is good cop, one is bad cop, and I'll just go to the person that's going to give me what I want. And that's not what we want to create, a culture of depending on who you talk to, you're going to get a different answer. We want the answer to be the same whether you talk to sales or the CSM or the individual that's the executive sponsor for that customer.

Andrew Marks: But you need a strong leader to be able to have those conversations. I've experienced too many times where there's been a leader who's been too weak that shied away from the conflict. I'm sorry, your job, and this is what we were talking about before we came on air, Kristi, when we were talking about the consulting work, your job as a leader is to lead your team, right? That's not just your title.

And so that means going to bat for them. That means having these types of difficult conversations. You expect your team to have difficult conversations with their customers and you're not going to have a difficult conversation with your peer whose organization is causing pain to your team. If you can't do that, you shouldn't be a leader.

Kristi Faltorusso: Oh gosh, that needs to be its own webinar. Can I just say one thing though on Eleni's point about the tying the sales to the renewals? I don't disagree with the intention behind that recommendation. I think it gets a little tricky if you're selling multi-year deals to tell a salesperson that you're not going to make money until this person renews if they're not renewing three to five years out.

So I think that there needs to be a realistic framework, whether you're tying them back to retention percentage as a whole for the book on a quarterly basis and saying, "You are all getting part of your commission based on our retention rates." Or there is some earlier milestone that indicates that this was aligned and there was strong adoption. So it could be an effective onboarding or something that is just sooner than the renewal.

Also, if a salesperson leaves, I have seen some organizations do this where a sales organization will pay an employee even after they have left the company if that customer renews. It was crazy. I only heard it once, but I loved the idea behind it because again, incentivizing good behavior, you didn't have to be present to earn that money. You can get a check later.

But I think it's important to understand all of the nuances, right? So just things to consider for folks that may have multi-year renewals in place, figure out something because your sales team is coin operated, they're in that role to make money. And if you tell them that they're not going to make their money for years, it's going to be hard to drive a certain level of agency and urgency behind their work.

Andrew Marks: That's an interesting idea to actually pay you after you've left.

Kristi Faltorusso: Crazy. I didn't believe it when I heard it. I was like, "Good for you all."

Andrew Marks: Once I'm done with you, I'm done with you. Okay? So just setting the expectation.

Let's get to some questions because we've got some questions. If I could ask my guests to take a quick look at that Q&A list, remember we go based off of most upvotes. So make sure to select your pull down menu to most upvotes. If you see a question on that list that you think you've got something to say that you want to jump in first, hit that answer live button. We do not type answers, folks. All of these questions though, as well as the answers will be in the transcript that we'll post on the website early next week along with the recording. So if you have to leave us here at the top of the hour, please check back on the website early next week when all that stuff will be posted.

All right. I see no ... Oh, I see a couple of people jumping in. No, I don't see anybody jumping in. All right, let's just start asking the question. So first question comes from Janelle. Janelle, thanks for joining us. Janelle asks, "How is AI being used, if at all, to improve or automate parts of the handoff process?" Anybody? Yes. Oh, Kristi. Oh my God, Kristi wants to talk. Yes, Kristi, what do you got?

Kristi Faltorusso: No, now I don't want to talk.

Andrew Marks: No, yes, you do.

Kristi Faltorusso: Okay, great. I had a good answer. So going back to the hygiene in the CRM, if all of the information is being captured properly, whether you're using Gong or Fathom or whatever your call recording is, all of those things, you can actually generate a really beautiful summary. We've actually created a ChatGPT, our own private GPT just for this that synthesize all the information that happened during the deal cycle with required outputs.

So it very much quickly just said, "Here's all the information that the CSM needs to be successful moving past that close." And so it took all of that information. It no longer required the salesperson to go fill in additional fields or to go fill out a doc. And then what happened there and what we did is that we added in just a short 15-minute conversation between the two stakeholders, and that was really just to answer questions.

So all that information was captured. They got everything that they needed, went back into calls. And then also with that prompt, the CSM could go ask the prompt questions. So even if the output was great and they still wanted to dig a little bit deeper into certain things, it would go back. And so again, we have all the call recordings and all the information there. You can ask additional information to make sure that you have everything you need, have a quick 15-minute sync to fill any gaps or to just make sure that you have everything you need to be successful. And that streamlined the process pretty significantly.

David Ellin: Kristi, you can even take that a step further and you can use AI to create automated handoffs for low value customers.

Kristi Faltorusso: Yeah.

David Ellin: Right? So you can have AI listen to all of the sales calls, understand what the customer's pain points are, what the desired areas of outcomes are, what the roadblocks might be, what products were sold, and then put that all in a report or in an email that goes to a shared CS team, if that's what you have for your long tail, and automate the entire process.

Kristi Faltorusso: Yeah. I didn't have all of the tools to connected, so only speaking from my workflow that I created. I had less access to technology.

Andrew Marks: Just make sure that you are structuring your prompts well, that you're validating the output. There's a dangerous piece of AI, we're actually getting ready to release an AI for Customer Facing Teams training program. I just finished recording it last night. So I'm hoping we have it ready in the next two weeks. But sometimes AI comes back with something that sounds very legitimate, convincing, and it's bullshit.

So please be careful before sending stuff to others in your organization or to your customers. You need to make sure you're validating and that you're also validating not only the data and what it's seeing, but the tone and how receptive the person who's going to be receiving that is going to be to what you have to say. Yes, AI can't hallucinate, Michael. Yes. They call it hallucination. I more refer to it as AI just being creative. AI is being creative.

Kristi Faltorusso: They fill in the gaps when there's missing information. They make assumptions.

Andrew Marks: They do because AI is not a thinking machine.

Kristi Faltorusso: Right. Right. Yeah. The other cool thing you could do is if you have the ability to summarize any account information. So if you've got a handoff, if a CSM is leaving, moving to another account, got promoted, whatever, and you're having one CSM take over for the other, it also does a really great job of synthesizing all of the information about the account over an extended period of time. So instead of having to go back and read all the call notes and go check all of the summaries and the updates and sentiment analysis and all of this, growth, contraction, all that, it'll synthesize that nicely. So if you're taking over an account from somebody, there's a really easy way to get up to speed fast. So that way, again, there feels like continuity and consistency for the customer.

Andrew Marks: Yeah, it's a great customer dossier creator.

Kristi Faltorusso: Yeah.

Andrew Marks: A hundred percent. We actually have a prompt as part of our program that we provide for that as well. Awesome. Anybody else want to weigh in on the AI piece before we move on?

Eleni Vorvis: I mean, just a suggestion, look into what existing technology you're already using, because in many cases there is an AI component. So rather than feeling like you need to go out and get the next shiny, bright object, because there are too many options out there. I think there's a platform actually that does handoff process and just focuses on that. That's very niche. So look into-

Kristi Faltorusso: Pretty sure it's called Handoff.

Eleni Vorvis: There you go. Look into what your CRM can do. Look at what a Gong can do or other call recordings. I think Chat is also great, but you may have existing technology, the features that you're just not taking advantage of.

Andrew Marks: You're thinking of a different website, Kristi. All right, let's go to the next question. Are you getting flush? You turned a little red there. All right, Cameron. Hey, thanks for joining us, Cameron.

Kristi Faltorusso: I have too much makeup for you to see what color my face really is.

Andrew Marks: Cameron asks, "I'm a founding CSM at my company and currently have been tasked with building my sales to CS handoff. I've already started, but based on today's conversation, I'd love to know where I should start. We have HubSpot, but we live in a lot of spreadsheets and little to no organization." David, you wanted to jump in on this one first. What have you got for Cameron?

David Ellin: Yeah, Cameron, this is a great question. And oftentimes nobody's prescribing for us what to do. We're being tasked with create this from scratch and our heads are spinning. I would say start with the information that you have to have in order to be successful. What is it that sales should know? Maybe they know it, maybe they don't, maybe they're good, maybe they're not, but what is it that you need to know to be successful?

So if you're doing onboarding, obviously you have to know what products were sold, but you also have to know what customizations were promised, what integrations were promised. Oftentimes those things get left off. Oh yeah, I forgot to tell you that we sold this basic tool, but we're adding three things to it. And those three things get missed and at the end of onboarding, the customer's pissed off and you didn't even know it.

So think about the things you must know. You should know why the customer came to your company to begin with.

Andrew Marks: What value?

David Ellin: What pain point are they trying to solve? You should know what their desired outcomes are. Maybe if you're advanced enough, it would be nice to break that into first value and then future value. What is the first thing they want to do with the product that they couldn't do before they came to us? And then what are the other desired outcomes they're looking to achieve?

If they have a specific timeframe in mind that they have to be live by to meet a commitment they made to their customers, you have to know that too, because you might have to compress a four-month onboarding into a two-month onboarding. So think about those things, and I'm sure everybody else has opinions on other things that you have to know as well, but that's a good starting point.

Andrew Marks: That was one of the most frustrating things that I faced when I was doing consulting, working with companies when they would complain. The post-sales team would complain, "Well, we don't understand what the value is, why they came to do business with us." That is a fundamental breakdown in your organization because your customer did not come to do business with you to spend money. Somebody knows that. Sales knows that. And the fact that you have to ask that question, this is a conversation I'm having with the CS leader, the fact that you have to ask that conversation during the kickoff call is a non-starter in my book. That information should-

David Ellin: And completely frustrating for the customer.

Andrew Marks: Pardon?

David Ellin: And completely frustrating for the customer.

Andrew Marks: Exactly. And this goes back to my example when I was at Intacct, frustrated the hell out of me. This is not okay. You guys, the sales team is selling the customer. There's a reason why they're buying from you. We need to understand that before we get on the phone with them. Anybody got something to add for Cameron?

Eleni Vorvis: Yeah, you need to know the stakeholders. That's really important. Not just, oh, pass me off to the team that's going to be using it. I need to be introduced to the executive sponsor. They will play a role in this engagement and the long-term success of the relationship. So understanding who each of those people are and-

Andrew Marks: And what makes them tick.

Eleni Vorvis: Right. Yes.

Andrew Marks: And what makes them tick.

Eleni Vorvis: What's their personality like?

Andrew Marks: Oh, this person's passive-aggressive. You should be capturing that, a hundred percent.

Eleni Vorvis: It helps. It helps to set you off on the right foot when you are then having the conversation with them in terms of how to speak to them and what resonates. Maybe there's also things they're really passionate about. But you also could do your research on that too using AI, but they should be capturing at least each of the different stakeholders that matter to your company.

Andrew Marks: Some good suggestions. Anybody else?

McKayl Bergman: I'd like to add something here. There's something I've done at numerous companies, which is, I call it the 100 questions list, and bear with me for a second here. The idea is that when we are saying what we predict is going to happen to the CSM, this account is green, this account is yellow, this account will renew, this account won't renew, whatever. When we do that, we're basing it on a degree of confidence, but that confidence has to come from somewhere.

And what's more important is often to know out of say 100 questions about the organization, which can include your stakeholders' personalities, how they tick, how they work. It can include the function, the organization layout. It can include all kinds of things. How many of those things do we just not know the answers to? And any of those things that we just don't know the answers to that we really kind of ought to, that is something that can blindside us.

So this 100 questions list relates to one of the questions here in the chat, or in the Q&A, as well. The idea is that we want to know what we don't know but ought to know and know that much like our lives, it's chapters being written over time and we can't get everything from day one. So having a very practical example notes template of that information that we want to capture, even if it is not what you're going to fill out in actual fields in the CRM, that comprehensive template can illustrate to your CSMs, especially as they're growing through their careers, what over time you really want to capture about an organization and give them a place to practice doing that.

So I think that would be something I would really encourage to most folks here, think in advance about what you really want to know, and then give yourself a timeline by which to know it.

Andrew Marks: Awesome. All right, let's move on. David, you can hit the done button under Cameron's question for me, please. Let's do the refresh. Our next question comes from Miguel. Miguel, thanks for the question and thanks for joining us today. What is the best way to do a handoff between sales and CS? Should a meeting between Sales, CS and the merchant always happen? And David, looks like you want to jump in on this again first.

David Ellin: Yeah.

Andrew Marks: So what have you got?

David Ellin: I'm going to start with it depends what customer segment you're talking about. If you're talking about enterprise, strategic or maybe commercial on the higher end, having a meeting between sales and CS is probably important even if it's only a 10 or 15 minute meeting. You should always do the internal meeting before you get on the phone with the customer. You both want to be completely aligned before you have that customer call.

If you're doing a handoff for your SMB or your long tail or your digital touch, whatever you want to call it, you might not need to have a meeting. You could do a report or you could do an email. You can have AI do that for you as we talked about before. And then whether the salesperson is on the kickoff call or not, personally, my preference is to have that salesperson on there. It holds them accountable for making sure that they delivered all of the information and the information was accurate. So I like that. Some sales leaders don't want their salespeople on those types of calls. They want them to go back and sell something else. But that's where I would start it.

Andrew Marks: I like that. I think it's important. I think it's important to hold sales accountable.

Eleni Vorvis: Yeah. I think the other thing is setting the expectation that the meeting is not for you to read through the information you were given beforehand. The meeting is to clarify and ask questions about anything that was unclear or anything that may be missing or raising your concerns. Everyone be an adult and look at the document and then come in. It's very obvious if you haven't done that. And again, that goes back to setting expectations of your teams to say, "We're going to make this a 15-minute meeting and here's why it can be a 15 meeting."

Andrew Marks: Or anything that may have changed. It's validation and it should be validation. There's nothing more frustrating for a customer than answering the same questions over and over again. Anybody else? We've got time for a few more questions. Ralph, thanks for joining us. Ralph asks, "What fields would you consider as critical as a single point of truth and resource for the whole post and pre-sales team?" I think right out of the gate, understanding why the customer's doing business with you is number one.

Eleni Vorvis: I think the technical field, so what David was mentioning. For the implementation team, what are the integrations, the APIs they'll be using? Are we building something custom? And any other expectations we've set around the implementation process. I think the stakeholder information, and obviously there's just the revenue components, like how long is this contract? Are there any specific things about the contract that we need to keep in mind because they may have to hit certain milestones or just anything that's unique outside of our standard agreement?

Andrew Marks: Promises that were made that may not be in the contract, but part of the discussion-

David Ellin: And timeline. And timeline.

Andrew Marks: Timelines.

David Ellin: Is there a compelling event that's going to happen where they need to be live and operating by for them to hit their commitments to other people?

Andrew Marks: And the next question from Beth, thank you, Beth, for joining us and asking the question, I think this is relevant. What information do you wish sales provided to CS that is consistently not provided? And I've already voiced my frustration about sales not providing why are they doing business with us? What's the value?

Kristi Faltorusso: I want to go a step further on that though. I want a SMART goal. I want something that I can measure. How are we measuring success? I think it's one thing to understand how they might be defining it or what is their objective, but I find that most CSMs struggle to get that. And listen, the struggle, I think we could put the onus on our customers. They don't even know, but then we're not guiding them properly. It's a chicken and egg thing. But that to me, the measurement of success would be something I would want to see that I see is often a blank field.

Andrew Marks: Well, let's be realistic. It's something that you have to define in order to move forward. You have to put that on a success plan. We have to have a target. How do we define success?

Kristi Faltorusso: Right.

Andrew Marks: A hundred percent agree with you. But to your point, I think customers have a hard time verbalizing that, describing it.

Kristi Faltorusso: I think at a company level, a lot of companies could do a better job of having something pre-designed that helps guide your customers to get there. I see a lot of companies that kind of like, "Well, tell us." And it's a blank sheet of paper and your customers don't know what they don't know. You're supposed to be the expert. I think companies could do a better job of having a framework to help guide these customers towards measurable outcomes and those defined metrics.

Andrew Marks: A hundred percent.

Kristi Faltorusso: Give them a little bit of a buffet.

Eleni Vorvis: An ROI calculator, because in many cases, you get the qualitative. Well, why do they buy? What's the problem they're trying to solve? And the answer that sales gives is something that's marketing jargon that's on our website. Sometimes I don't know if they're fully understanding how to ask the question in discovery on how is this going to impact your business? And if as an organization, you don't know how to quantify either time savings, increase in revenue, increase in efficiency and there being that shared language, then you're leaving success up to the executive sponsor to decide and not maybe even share with you how he or she is going to measure success and then you're never going to win.

So I think a recommendation is if you don't have the ability to articulate it in a quantifiable way, then that exercise needs to happen as an organization so at least everyone is consistently asking the question and documenting the information because I've seen that.

Andrew Marks: I agree with that. I think you need to have an inventory. Here are the typical value that a customer can get and you use that as a tool. But here's another opportunity where you can leverage AI and it's actually something that we talk about in the training program around this concept called tree of thoughts. Based off of all this input, I want you to give me a couple of different options on how we could frame a value proposition for this customer. Because it doesn't matter what we put together, we have to be able to translate that into the customer's world.

So it's not just, "Oh, I've got this list." There's no easy button here. And there shouldn't be an easy button because this is one of the most important things you can do in your customer facing role, is understanding and articulating the value that they're getting from doing business with you. If you want your customer to buy more from you, whether that's a renewal or it's an expansion, you better be damn clear on here's the value you're getting and tying it to quantifiable, specific outcomes before you can even begin to ask them for more money, identifying and communicating value.

McKayl Bergman: And I want to add to this too, these are really excellent points. There's a critical function here is how not just our own leadership teams and our own team members understand, but how our customers understand objectives and key results. If a customer, if your team of customers, five core contacts, whoever they are, cannot articulate and cannot design well-written objectives, key results, measurable results, then they will struggle. They will struggle through every part of your process because they can't prove value.

So it's critical that we have during implementation and regularly during a relationship with a customer post-implementation, essentially an OKR workshop where we teach our customers, "Hey, just to refresh you, you might remember this, here's how you work through an OKR. I want to do this with you. I want to take an hour to question, think deeply and really create those objective statements." Because like Kristi mentioned, like Eleni mentioned, if we say, "What are your objectives?" they're just going to give us a garbage sentence and they don't really know yet. It takes time to think it through.

David Ellin: I want to separate this by going back to Beth's question about the sales to CS handoff, and then where we're taking it right now, and that is understanding how to define success long-term so that we could retain and expand our customers.

In my opinion, success plans need to start with the sales rep in the latter stages of the sales process. And in most cases, I understand that users, admins, they may not be able to articulate what success should look like in the future, but when somebody is buying a product, they're typically more of a senior executive, they're a decision maker. They should be able to clearly articulate, "I need to raise this from this percent to this percent. I need to generate this from this level to this level." So we should know that.

And the answer to best question, in my opinion, is that information that the sales rep has heard from the buyer needs to be translated to the post-sales team. Then, McKayl, to your point, and Andrew, to your point, we need to teach our CSMs how to ask the right discovery questions to understand additional pain points and what those future desired outcomes should look like, and then define success in the customer's words.

Andrew Marks: By the way, that's in the training as well. I know. What do you want from me.

Eleni Vorvis: Can I say one more thing because there is another question?

Andrew Marks: I'm trying to sell my stuff here. Okay?

Eleni Vorvis: There's another question we don't ask in the process, right? We don't ask the customer how they're measuring internally today because we have data that's in our platform, but in many cases to articulate an ROI and get a CFO or a economic buyer to sign off, there are metrics that they're using themselves.

And that's where our data and their data needs to be married together and delivered in a value review to paint the full picture. And I think at times we just get shy to ask for that or we don't set that up at front. So if that was a question during the sales process, it would help everyone at the company working towards this goal of getting the customer value. And that's something I-

Andrew Marks: The whole shy thing, I think you nailed it with the shy thing. And the ridiculous part of that, Eleni, is that the person who you would be asking that information from is likely the person who was the one who said, "Hey, we need this vendor." So they have a motivation to supply you with that information so that they look good. Hey, I look like the smartest person inside these four walls because I partnered up with you.

Eleni Vorvis: Yeah. And if they don't want to share it, then I think you voice your concern, why? Because we're sharing data from our platform and you've got metrics too. So I think that'll indicate how successful is this relationship going to be and how much is it going to be, we have to give you everything, but you're not going to work with us in return. And I think it gives you a sense of, can this customer thrive in working with us and are they going to do their work? Because we talk a lot about what we need to do to get things done, but there's a certain level of expectation on the customer side on what they need to do in this relationship as well.

Andrew Marks: Well, and that's what's laid out in the success plan, also something we teach. But we're going to wrap things up. One last question I want to answer for Theresa. Do you feel professional services falls under CS or should they be separate departments or teams? I personally believe they should fall under CS because they play a really important role in helping the customer get first time to value, get value out of the solution. It's all Customer Success. Everything post-sales should be Customer Success.

And with that, we've reached the end of today's session. I want to start by thanking our panelists for sharing their perspectives and their experiences, of course, my lovely co-host, Kristi, for not beating me up too much. These conversations are only as valuable as the people willing to be honest about what's actually happening in the work. And we truly appreciate you all making the time. To everyone who joined us live, thank you for your questions, your engagement, and for being part of this community.

If you found today's discussion useful, we'd love for you to continue the conversation on LinkedIn. Tag one of us or SuccessHACKER and share a takeaway that struck with you. Our next CS Mastermind is coming up on April 15th where we'll be exploring how Customer Success teams avoid taxes. No, how Customer Success teams move beyond product features to consistently driving, measuring, communicating the value that matters the most to customers. So a kind of follow on from what we were just wrapping up with. And once again, you might be surprised, but I definitely have something to say on that. We also have a training program. We're still looking for a panelist for that one, by the way. So if you're interested in participating, please let us know.

Finally, great customer focused professionals don't pretend to have all the answers, but they do know where to find them. And that's exactly why we created this series. Have a great rest of your day and month, and we'll see you next time.

CS Mastermind #82 Transcript: Personalization at Scale: Leveraging AI in CS

As customer expectations continue to rise, delivering personalized experiences at scale has become one of the biggest challenges in Customer Success. AI offers powerful opportunities to tailor communication, anticipate customer needs, and deliver value-aligned recommendations across every account. From intelligent segmentation and automated insights to personalized content and engagement triggers, AI enables CSMs to meet customers with the right message at the right time.

The most successful CS organizations are those that figure out how to blend the efficiency of AI with the authenticity of human connection. This webcast will explore how AI-driven tools can enhance customer engagement, improve retention, and reduce manual workload without sacrificing empathy or trust.

In this CS Mastermind session, hosted by Kristi Faltorusso, our panelists discussed:

• The definition of “personalization at scale” and how AI makes it possible

• AI tools that have the biggest impact on improving personalized customer engagement

• Ensuring AI-driven automation still feels human, empathetic, and relationship-centered

• Signals or data points that AI can analyze to effectively tailor engagement

• Common pitfalls faced when scaling personalization with AI

• Ethical considerations for using AI to personalize communications

This webcast featured:

• Rebecca Nerad, Vice President of Customer Success at Advantive

• Rob Zambito, Founder & CEO at Success Scaled Consulting

• Somer Morton, Customer Success Manager, Midmarket at Highspot

Top Takeaways:  

1. Rich contextual signals differentiate true personalization from surface-level automation. CSMs who operationalize workflows to capture and act on signals such as stakeholder job changes, industry news, and product usage trends, can create outreach that feels relevant, not templated. AI makes this depth of personalization achievable across an entire portfolio, not just a handful of accounts.

2. Customer Success teams must intentionally define what to automate and what to keep human. Routine touchpoints are strong candidates for automation, while emotionally complex conversations and high-stakes renewals demand a human presence that AI cannot replicate. Drawing this distinction intentionally is what keeps scaled personalization trustworthy.
   

3. AI-powered meeting intelligence tools allow Customer Success Managers to analyze important and extensive data before customer calls. Instead of spending hours manually reviewing notes, CSMs can use these key summaries to walk into conversations prepared and focused on strategy.

4. Customer Success organizations need clear governance before scaling AI-driven workflows. Defined guidelines around tool usage, customer data handling, and decision boundaries prevent inconsistency and mediate risk. Organizations that establish this structure first, rather than utilizing the tool without defined plans, are the ones that make personalization at scale sustainable.

5. Customer Success Managers can use AI to simulate objections, test messaging, and challenge their own assumptions before customer conversations. Treating AI as a thought partner rather than a content generator is what elevates AI from an efficiency tool to a strategic one.

6. Customer Success leaders should plan for a short-term adjustment period when introducing AI workflows. Leaders who plan for a short-term performance dip, measure net impact over time, and leverage early adopters as internal champions build AI habits that actually stick. Managing this change well is what turns AI adoption into a durable competitive advantage.

Session Replay

Session Transcript

NOTE: The following transcript has been edited for clarity and content where necessary to improve readability.

Kristi Faltorusso: Hello everyone. I'm Kristi Faltorusso. Thank you so much for joining the SuccessCOACHING monthly CS Mastermind Webcast, where we bring together professionals from across the customer experience ecosystem, from Customer Success Managers to Support Specialists, and everyone in between. Today's session is brought to you by SuccessCOACHING, where they have helped customer facing professionals from almost 100 countries, developing the skills that they need to excel. Whether you're in Customer Success, Support, or any customer facing role, you can find the right program for your learning style. You can find all the details of their offering on their website successcoaching.co, or in the chat. Ashli is going to go drop any links for you there, along with any coupon codes that they might be offering.

The CS Mastermind is about real world experience. So no theory, no theory frameworks here. We're going to talk about real practical advice and actionable insights that you can apply immediately to your role. So today's topic, we're going to talk about how to explore personalization of our customer experience at scale using AI.

To get us started, I'm going to walk you through a few housekeeping updates, and then we'll dive in and do some introductions. So before we begin, please note we are recording this session. We'll share the replay next week. So be patient. That will be in your inbox. Please use the Q&A buttons for any questions that you have. So please don't drop them in the chat. Use the Q&A functionality in the Zoom window. Drop your questions there. And feel free to upvote. We're going to sort it by upvoting. So at the end of our session today, those will be the ones that will get priority over any others in the discussion. LinkedIn Live viewers, if you have any questions for us, post them directly into the comments. We'll make sure that those are passed over. So don't worry about that.

I am super excited for today's conversation, and to introduce my friends and our panelists who are going to be sharing their insights with us today. So we're going to get started. Alphabetical order as usual. So Rebecca, that means we're going to start with you.

Rebecca Nerad: Thanks, Kristi. I'm Rebecca Nerad, the Vice President of Customer Success at Advantive. I've been in Customer Success, as I like to say, well before we had the term Customer Success, for 25 years now. While I've had leadership roles in support and marketing, most of my focus has been CS, driving value for our customers, and most of that time owning the renewal function.

I've been in the supply chain and operation software industry for my entire career. And the last 10 years have had a particular focus around mergers and acquisitions. So acquiring companies who in many cases don't have a Customer Success function. And so bringing some of our best practices to the processes and to the people at those organizations to help them scale.

Kristi Faltorusso: Very good. Rob?

Rob Zambito: Yeah, my turn next. I'm Rob. Rob Zambito, the Founder and CEO of Success Scaled Consulting. And what we do is we build and scale Customer Success teams. I mean, we color it with different terminology depending on who you are, between helping Customer Success teams be more proactive and revenue generating rather than reactive cost centers, or driving NRR and improving margins or whatever.

But regardless, what we do is we build and scale Customer Success team. So I trust that everybody here in the room knows what that means. So we've done it about 40 times now, across 40 or so clients rather, from first dollar to unicorn. We have a core six to nine month program that we run folks through. We also have recently spun off Systems Scaled, so that's like our RevOps focus or CSOps focus of the business. And then Talent Scaled where we're happy to help people find jobs.

So it's been really fun. I've been in Customer Success for 10 years, depending on where you draw the start line, 11 years maybe. But it wasn't always this pretty. I got my start, Kristi knows this, living in the basement of my first customer's house. And people are out here on LinkedIn talking about being customer centric. I was like, I couldn't be farther away from my customer. I literally lived in his house. So that's me in a nutshell.

Kristi Faltorusso: Thanks Rob. Somer.

Somer Morton: Nice to meet you everyone. My name is Somer Morton. Unlike my beautiful peers here, I'm new into Customer Success, and so had a varied career, but I started my CS journey nearly two years ago. Met a dude in the driveway of my wife's parents. And he was like, "Hey, your sort of unique of skill set from sales operations," I helped launch Tesla into Australia, and I've helped build an entire leasing portfolio for a boutique investment bank and sort of productize it. So there's a lot of B2B stuff from in there.

And he was like, "You'd be great at a Customer Success Manager role." And I was like, "Oh, weird." So I kind of dipped my foot in, dove in, and I've just been kind of sprinting to keep up. And I now spend my days and I work at Highspot. I spend my days working with Enablement teams and Sales leaders, helping to integrate AI into individual contributors' roles so that these companies can keep growing, or sometimes stop shrinking. And so I'm really excited to lend a bit of a different perspective, very much from a hands-on, what do we actually go do. Whereas Rob and Rebecca are thinking about things from the top down about what's possible. So yeah, super excited.

Kristi Faltorusso: I love that. We got three strong voices for today's conversation. So that said, I'm going to get us started and tee us up for this discussion today. So let's get started with the simple truth. Customers today expect to feel known. I don't think that that's different though. I feel like they've always wanted to be known. But they expect you to understand their goals, anticipate the challenges, and reach out with relevance, not just generic check-ins or template updates. At the same time, you've got CSM portfolios that are growing, resources are tight. The expectation to do more with less has never been higher.

So here's the tension. How do you make every customer feel like your only customer when you're managing hundreds? So this is where AI enters the conversation, not as a replacement for relationships, but as a force multiplier for them. So when used thoughtfully, AI can help surface insights, trigger timely outreach, and tailor messaging in ways that would be impossible to do manually at scale. But the real opportunity isn't automation alone, it's augmentation. It's using technology to free up time and sharpen focus so that human moments matter even more.

So today we're exploring how Customer Success organizations can blend efficiency with empathy and how they can deliver personalized experiences across the entire book of business without losing the authenticity that builds trust. So to get us kicked off, we're going to start, what does personalization at scale mean in modern Customer Success, and how does AI make that possible? So Rebecca, why don't you get us started today?

Rebecca Nerad: To me, personalization at scale means you have to deliver contextually relevant value. So you can't have a human interaction for every customer in the way that they want. And we have tons of data and insights. And what AI helps us do is gather all of that to help each individual customer feel understood, even though we're using the digital first model. So if we focus on roles and segments and we'll get into some of that, but we're leveraging the AI to inform us about this particular, maybe it's the customer segment, maybe it's the product that they're using. Ideally it's down to the customer level, but we can certainly seem more mature about the industry or what's been going on with that customer if we leverage the data to make them feel heard in a way that they hadn't been before.

Kristi Faltorusso: I love that. All right, Somer, I'm going to direct this next one to you. I want to hear your thoughts on this because you're coming at it from a different perspective. So when you think about personalization at scale in modern Customer Success, how does AI make that possible?

Somer Morton: Absolutely. So while my leadership is thinking about what Rebecca's saying right now, I'm thinking about across my book and my time that I have available, how am I able to connect with my customers? And the way that our customers work, we have four different personas, three different power levels. So there's a huge number of different categories of relevant information that I need to approach within one organization.

And so the two key pieces here are, in the past, and Rob and I have sparred on this, I did think that personalization existed at odds with scale. That the more personal something got, the more time it took to make it personal, and therefore the less scalable it was. Now we're able to outsource or I'm able to outsource a lot of the reading of notes or reviewing call transcripts or anything like that, the information gathering processes. And I can go into a call with much less prep, and I can have a very targeted specific conversation without needing to redive into discovery. And that allows me to be personal and relevant and timely to each of my customers across my book.

Kristi Faltorusso: I love that. Now, obviously, Rob, you've got a company where scaled is in your name. So when you think about personalization at scale, what are your thoughts here?

Rob Zambito: Yeah. I mean obviously I'm always just trying to teach myself the lessons that I teach my clients and put it into practice and dog food my own advice. But yeah, so it's interesting too. Because as a consultant, my job is not that different from that of a CSM. In fact, the best CSMs are those who are consultative and they provide their clients advice and value add guidance that is very similar to consulting.

So the interesting thing is, and what we've even been dog fooding with me and my team, is since I was in college, I remember I had a Marketing professor who said, "Keep trying to solve for an N of one. Try to solve for the individual persona as specific as you can." And I remember rolling my eyes thinking, yeah, this guy is a prolific Marketing professor, but really that's not possible with a scaled business.

And so now I've just felt like fundamentally unlocked in many ways because large language models do allow me to understand my clients, even just refreshing myself, like Somer was saying, before calls with a lot of the depth of understanding that that client deserves. So in the past, personalization at scale meant like, oh, great, you have a digital Marketing campaign or a digital CS campaign with merge tags that I know we've all gotten the hello first name, those merge tags that they give.

Kristi Faltorusso: The standard marketing tokens like the inserts. Yes.

Rob Zambito: Yeah, yeah, yeah. And that's where I cut my teeth in this original domain. But I just stayed fascinated with this problem of trying to solve for an N of one. And then only now do I actually find that there's tooling that allows me to provide the right outreach with the right messaging to the right persona with the right timing. All of which I've been really bad at in the past. And so that was the interesting, like Somer said, we sparred about this, I think the interesting thing is that to me now personalization and scale, they're more orthogonal now. They're sort of at a right angle to each other instead of on a spectrum where you have to inherently go one way or the other. And there's this interesting new quadrant of personalization and scale that I'm super fascinated with.

Kristi Faltorusso: Very good. Okay. Well listen, I am sure, like many of you, we're seeing an explosion of technology in support of this. I feel like every time I log into anything, there's a new tool being marketed to me to go solve some other problem that I don't even know yet that I have. So I'd be curious to hear from you guys, what does the tech stack look like that is enabling and empowering you all to think about personalization at scale?

Somer Morton: I got the smallest one, so I'll go first. My company is an AI first company. So my products, we dog food, it's baked into my workflow. But we have meeting intelligence, so it's recording all of my calls, ingesting all of my emails to create an account timeline so I can query that via an agent. It allows me to go in and extract sentiment analysis, business objectives, everything you might want. So I ask it a question. So that's Highspot, but Gong has a very similar thing, and there's a whole bunch of spin-off AI first companies.

Then we have an LLM, we use Gemini. But ChatGPT, whatever, [inaudible]. I have a Gem, which is like, what are the... what is it they call, a GPT on ChatGPT. It's referencing Customer Success best practices as the context of my role and the context of my company. And then I have a pre-created prompt, and I'm able to jump in there and sort of spar with it where I will bring my thoughts on what's happening. And I might drop a transcript in and I can extract a success plan out of it.

So yeah, they're the two biggest, biggest pieces. I know there's heaps, the potential and capable and my colleagues will jump into it. I have a lot of security guardrails I cannot go around. And so for some of you that are ICs on the call, one of your objections might be I can't because it's not my decision. And then the question then becomes, well, what can I do that is within my control that could save me 15 minutes times 10? Where can I shave off little pieces of my workflow?

And just yesterday, I literally was feeling frustrated about writing a follow-up email, and I noticed that Gemini has an agent within my Gmail. So I went in there, I was just like, write me a follow-up email to each individual member of this, it was like after a business review, singling out their action items, and then politely get follow up. And then I did it and it was great. And I sent out all of those emails, I adjusted them a little bit, and I saved myself probably 20 minutes.

Kristi Faltorusso: I think we forget that it's okay to be better, not best. Incremental improvements around efficiency is still better than where we were. So better not best is absolutely fine. And Somer, I think you gave some really great use cases there. And if I'm being honest, I don't think people think enough about security. So good on your company for really putting some guardrails around that because it's getting crazy out there. All right, Rob, what's in your tech stack?

Rob Zambito: I just wanted to mention, Somer, I love that you mentioned sparring with your AI because Kristi was on a really good panel last month that I got to see, which was about how to use AI as, Kristi what was the word, a provocateur I think was the word that went around. I think that's so important because AI can be your best friend to sharpen your thinking and it can be also your best friend where it's like a total yes person, and it's like you're absolutely right about anything you say.

For me, so I'll mention one that you just made me think about Somer, but the main ones that I'm using day to day is I think about the different touch points of the customer journey. I don't think about what are the tools? I think about the journey points that I'm touching, and there's seven. So it's Support, it's onboarding, it's customer health, it's renewals, it's churn handling, it's upsell, and it's customer advocacy. And if you didn't follow all that, it's okay. I'm sure I can make a LinkedIn post or something out of it.

But regardless, we're all doing these things every day. Some of us have a narrower scope within that. But when I look across those, I think some of the more interesting, the key ones that I really like to think about, are when I think about churn handling, that's a really big one where I've leveraged AI for objection handling exercises. So that the first time I have a conversation with a customer, it's not the first time. Because I've trained a custom GPT on that customer, that interaction, that problem set that I'm trying to solve, and what the exit criteria are from that churn or cancellation moment.

There's really interesting new tooling coming out around customer health as well. I use a meeting recorder called Spiky, that's my total favorite because my academic background is in behavioral science, and Spiky is all about deep, deep sentiment analysis. So I could look at five clients and find the five points last week where clients showed signs of anger or showed signs of excitement. And that's an unheard of thing for me in prior lives when I've managed teams. So there's some really interesting ways to use that to feed health scoring. Although sentiment, I think we all know in this virtual room, that sentiment and health scores and forecasting, they're all different but related concepts.

And then the last thing I was just going to mention is there's a cool tool on the onboarding front that I've just been checking out, brand new, called Quarterzip, that does in-app, it does in-app guidance so that if you're struggling as a user to set up something in the admin screen, instead of having to have an LMS on your separate screen that teaches you how to use the admin screen, and I love LMSs, don't get me wrong, but there can be real-time contextual evidence of like, okay, you seem to be struggling here. How can we help you overcome this integration challenge, this configuration challenge, or whatever, even just a usability challenge. So there's a lot of really cool ones that I've been checking out.

Kristi Faltorusso: Rebecca, what do you got? What's in your tech stack?

Rebecca Nerad: It's going to lean right into some of what Rob shared. First, I'm very fortunate to be at an AI forward company, not just in our products, but in the way that we lead and encourage across the board. So everyone has access to ChatGPT. And because it's in our firewall, we are able to send customer specific examples where many people can't. So I mean, step number one, you have to use your customer data responsibly within the expected boundaries, as Somer was saying. You can't just send out examples, whereas the idea of being able to say, here are two contracts, what's the difference between the SLAs here? That's guidance that it really depends on the specifics of your tools. And in my case, I feel like my team's able to do a lot of that type of research.

I want to give one example though, where we use AI, and this was ChatGPT again, but it's so related to what Rob said, that I built an agent about objection handling. And imagine sending the transcripts for the past year of all of our renewal desk where I'm giving approval. We have guardrails. The team comes because a customer wants an exception. We talk about pricing, bundling, all these rule sets, and with real examples.

So now we have an agent where the CSM can go and ask for those. These are the things the customer's asking for. And so when they're coming, asking for a recommendation if it breaks a guardrail, they're already getting guidance, and what this provides them is both the internal coaching on what rules and what they recommend, what I've approved in the past, as well as here's a customer facing email to represent how you respond to some of these points. So that's just one of many examples that we have for tools, again, around more internal rules.

As far as one other call out from a tech stack perspective, I want to give a shout out to Glyphic. So all of our calls are recorded, this is sales and CS, are recorded using Glyphic. And it's also good. Rob was talking about sentiment analysis. And so this captures especially for the individuals, but also for the managers. When I'm able to go back and see across a set of customers or trends, there are a lot of insights that are gathered from this.

And where it makes a difference in a CSM's life is that they're able to send it off and make use of it. So it says, Somer, oh, I have a QBR coming up. It summarizes the most important points from the prior one, or even who's the point of contact. I'm a new CSM assigned to this customer. It's able to say, oh, this is the person who'll handle your invoices and this is the primary point of contact based on a bunch of information that we would normally have to go and chase.

And what's great is at the end it'll recommend in this sentiment example to say, wow, that customer, they were just talking about canceling or they were really frustrated. Something bad came out of that. It'll say, should we change the sentiment value back in your health, or in your CRM, in our case, it's Salesforce, should we change this? And all you do is go, yeah, push. So it takes the notes because it's integrated to Salesforce on what we've mapped for our fields, makes a recommendation, and we just go, yep, this and this and this. I want to update. Go. So if you think about the amount of time it saves from a note taking and going and entering into the system, gathering information before you're meeting with a customer, that really saves a lot of time.

Kristi Faltorusso: I love that. You know what's interesting, I didn't hear anybody talk about Claude.

Rob Zambito: I'm actually about to break up with ChatGPT.

Kristi Faltorusso: Right. Same. So I just cleared off one of my computers just to have it ready to do co-work on it. So that way from a security standpoint, I don't have anything on there, so no files or anything I don't want it to access. So I have a clean computer all ready for co-work. But I was surprised. I feel like Claude, I mean they did make this huge investment in their Super Bowl commercial, so I figured everyone would be using it and talking about it now.

Rob Zambito: I think if I break up with ChatGPT will be like, you're absolutely right, you should break up.

Kristi Faltorusso: I heard Claude's a little saucy though, so I don't know, for my self-esteem, I might not be able to handle it. We'll see how it goes.

Rob Zambito: That's what I want.

Rebecca Nerad: I like the question. I'm on the cusp, Kristi. I'm actually at a place where before I lean in any further from a more personal and some of the other, I think I'm going to start Claude on the side.

Kristi Faltorusso: So we might all just have to come back and do a Claude workshop together where we talk about all the cool things we were able to do with it once we've done it. I saw somebody in the chat mentioned Gamma. I'm like, I am a Gamma junkie for quick deck building and making all that stuff. And it's really cool what you can integrate that with. And so when you talk about personalization, if the workflow that you're required to execute on does require presentations, please go look at Gamma. Not sponsored, but love that.

Rebecca Nerad: I've heard the same from a leader in AI. And I have a leadership roundtable around that and that was one of the outputs of that.

Kristi Faltorusso: I'm like Gamma doesn't charge me enough per month for the amount I create in it. Let's just put it that way.

Rebecca Nerad: Yeah.

Kristi Faltorusso: All right, well listen, I know that we probably all could rattle off hundreds of tools because every day there's 100 new tools coming to market. So hopefully that was interesting for you guys. You chatted, you jotted down a bunch of new tools. Hopefully there was something new that you can go and explore after this. Let's keep the conversation going here.

So for you guys, how can CSMs ensure AI driven automation still feels human, empathetic, and relationship centered? Because I feel like there is fear about that. Personalization can still feel generic even though it's personalized. So how do we keep it authentic and actually feel inspired by humans?

Rob Zambito: I'll be happy to dive in.

Kristi Faltorusso: Somer, go. Rob, somebody.

Rob Zambito: I'm happy to dive in. So there's three lenses that I try to always look through. The persona, the message, and the timing. Those are the most important. There are a lot of other ancillary lenses to look through, like we mentioned security before and things like that. Now there's a lot of other things to be thinking about, but the three most important things in my mind are do I have the right persona, is this the right message, and is this the right timing?

The really cool thing that I've started to see is a lot of activity now around the third part of that. Timing is the hardest thing. If you think about it, a lot of times the old fashioned model is you wait for a QBR to talk about new features, new value, new expansion opportunities, or whatever. But now it's like that type of thing can be real time triggered. There can be agentic messaging that enters a customer into an expansion cycle. And I, as the operator of that system, my job becomes so much more timely and so much more precise that I don't have to wait a month, two months, three months for that conversation to be had. So that's been pretty cool.

Kristi Faltorusso: Rob, I got to challenge your three, and can I put a fourth in there? You don't have to keep it.

Rob Zambito: Yeah, please.

Kristi Faltorusso: But I'm going to put it in, but you don't have to keep it. You didn't mention data. Because I feel like the context would also be a critical element of that. So I absolutely love that, the persona, the message, the trigger, and timing. I love that. But I feel like those can only be true if, right, they can only be effective if the context that we're pulling from is good to make it feel human. And I don't mean generic data like your renewal date, your company name, which I feel like is fine. It's seemingly where everyone's starting, but the rich context, the good stuff.

Rob Zambito: Somer, Rebecca, help me out.

Rebecca Nerad: For me-

Somer Morton: Well just... You go, Rebecca.

Rebecca Nerad: Well, for me it's about automation and I are handling what's predictable in all the data and all of that. But humans still need to handle the complexity and the emotion and the value. And I think we fail most when we try to just automate and send, and don't take the time to really think about the context because we're trying to be too fast. And so in particular when you think about where we're driving, the how we're engaging with customers is where we need to take the time to do that right.

Somer Morton: I agree.

Kristi Faltorusso: Rebecca, how do you think about that at scale though? I mean think about the organization that has thousands of smaller customers where we really can't involve that human intervention, we'll refer to it as. What's your level of comfort of just letting some of these things run?

Rebecca Nerad: Ideally you still have small segment. You definitely can't hit it on a one-to-one, you have to hit it on a one-to-many. But it's an awareness of let's say there's a product line that you haven't been updating as frequently or has had more support struggles. Or you have to be aware instead of just, so your messaging, even though it's to a set of customers, has to be different than the way that you may be approaching others. And to me, that's what matters. It's when I talk about the how. Instead of going, hey, we have another cool announcement, or here's your latest release notes about something. If there's something you have to tackle that hasn't been good or hasn't been great, make sure you're not just making everything sound peppy and enthusiastic. To me, and that still can apply across a set of customers and not an individual way. It's being mindful for that subset on what you're saying and how.

Kristi Faltorusso: Somer.

Somer Morton: So I have more opinion on this particular space than delivery because we are really high touch with all of our customers by the nature of our product. And so from a personal experience standpoint of hands-on keyboard work, the way I leverage AI is different to how I would if I was building something. I would automate a lot more. But in my actual day to day it's about how much time can I free up to have a conversation with my solution owner to help equip them with the skill of change management and coach them through a conversation they might be having in an executive office.

That is a high leverage conversation that's very, very personal because I know their procurement leader in whatever it happens to be so I can enable them, versus us spending time talking about some other stuff or me spending time researching. So that's how I apply it in my real world life. But that's not AI driven automation, so I don't have as much value to add here that's not theory crafting, which I don't necessarily want to go down because that's a road of infinite possibilities.

Rob Zambito: If I could add just a brief note on that.

Kristi Faltorusso: You can always.

Rob Zambito: Yeah, one of the things I've recommended to myself and a lot of clients that I work with is go through the journey yourself of using the AI stuff that you're feeding your customers. And it's just not common enough that we do that. So I try to encourage all my clients every quarter, if not every six months, go through the customer journey by segment. Pretend you're a customer. And so many of us are in this position where we're like, I don't understand why no one's trusting the AI bot that's supposed to be doing all this stuff. And it's like, well, do you trust AI bots when you use them?

I mean you can quickly realize it actually unlocks a lot of scale and a lot of internal empathy with your team if you actually treat these AI tools that you feed your customers almost like they're their own product launches. As if it was a new product launch that your team was launching. So then you start to see like, oh yeah, I guess I don't really read release notes, so why would I assume my customers would. Some of my clients are working with customers who are realtors or home builders, and a lot of times they're just in their truck or they're on the road. They're not taking the time to read release notes. So that's been helpful too.

Rebecca Nerad: I think too, when we think of leveraging AI, and not just in CS, where my brain goes is a little more support on this side, but it's still relevant when we want to make customers be able to, instead of logging a ticket, they're coming and they're leveraging this whole set of, it's all our release notes and all our support information.

The importance of taking the lessons we've learned from LMS that want to please everybody, they want to give you an answer, to be able to train it to say I don't know, which they don't naturally do. They naturally want to make up an answer. But we have to create rule sets for the AI that we're presenting to our customers so it doesn't do that. So it gets to a point where it goes, I've looked in all the release notes, I've looked in all the support. If I've looked at all this history, I don't know, I don't know. Would you like me to log a support ticket for you, instead of inventing something. And that's part of the journey that we're finding out with AI and LLMS. And the same actually applies to some of these agents we were talking about internally, Rob, is like where you say stop. This is what we know. Don't advise pass this because we don't know.

Kristi Faltorusso: And it's great context. All right. So we've kind of talked about these motions, but we also know that these things are only as good as the data that supports them and the context. So when you guys are thinking about the signals or the different data points that AI can analyze today, or what you wish it would, to tailor these engagements or approaches more effectively, what are some of the things that you think are critical data points or signals for these tools?

Rob Zambito: For me, they go back to that seven points in the customer journey that I mentioned. I would encourage everyone here to ask yourself, am I getting notified of a stalled onboarding? Am I getting notified of usage drops? And am I making the most out of that information where I can even automatically trigger messaging to the user ideally in real time to resolve that? Am I surfacing customer feedback and customer sentiment automatically and in a scalable way?

And then even rounding out the customer journey. Am I automatically learning about the customer's, not just the customer's upcoming renewal, but the risks around that, the context around that, the goal achievement around that, the value outcomes that customer received? All the way through to expansion and advocacy. So if you go through those different points in the journey, I'd be happy to throw them back in the check in the chat, usually most teams have some room for more real time visibility and maybe agentic action at one of those points. So those are the main buckets of data that I think through.

Rebecca Nerad: I like your point, Rob, and I think when we think about things like usage, support tickets, that type of thing, unfortunately that's looking in the rear view. By the time that the usage is dropping, it might be later. So I think that's important. That's important that we leverage the technology to update those CSMs. So they say, oh, this has dropped and they're notifying them so the CSM isn't going and looking that they're receiving the alert.

Where I think AI starts to make the difference is across the patterns, across all the data sets and all the customers, that says, hey, this set of customers tends to be trending lower in sentiment, and it seems to be related to the implementation or the delays in this area. And that's where you can use, again across that data set, to be able to say, what do I need to think about and understand for this set of customers before it happens to others? How do I identify potential risk as a trend? That's where, to me, it's made more of a difference to being able to predict because of the data.

Somer Morton: And to add an individual contributor's lens on, I'm managing a book of business, and some of the things I need to look at are based around my customers and what's happening in their world, what's happening in their industry, what's happening to their business.

And so a really simple one that everyone can do is set up, every individual contributor, set up Google alerts to run once per week for all the customers in your book of business and to give it to you in one bulk email. Then you can drop that into an LLM with a predefined prompt to be able to then extract out of it specific insights that you can then deliver into your customer quickly. And so maybe they're going through an acquisition where they are acquiring a company. So for me, that's new seats. So I want to be on board.

Ideally my customer tells me as soon as they know, but this gives me targeted outreach that I can go and help grow the account. Or the inverse, they're being acquired, so then I can go and start taking action. So for me it's about data, which is just there's no context. So I try to use AI wherever I can to apply context to turn it into insight, and then shorten the window between insight and action. Because everything is about the speed to relevant action for me because I have a finite period of time to go and apply. Whilst my Robs and my Rebeccas are thinking about the system as a whole to improve my ability to perform and execute within it.

Rebecca Nerad: I think the challenge, a lot of what we're talking about today, it's this combination of digital to scale across hundreds and hundreds, or the CSM who has 10 strategic customers. They're very different solves, but at the same time we can still do things faster. We're able to be more strategic advisors because we aren't parsing through the data.

Somer, I want to share an example that you made me think of, that a strategic account manager at my company used. Imagine saying we are wanting to upsell within a particular software space, and saying this customer has posted on LinkedIn about this type of industry challenge. Has anybody been talking about struggles they've had in this particular business area that our solution solves?

And to be able to look at across all of those users and stakeholders at a particular customer and give that feedback is really insightful. And maybe it sounds dodgy if we're using that to potentially sell more. But what we're doing, they're publicly sharing like here's a struggle that my business is facing or here's something that I'm interested to learn more about. And it really lets us get closer to what their problems are and being more mindful in leveraging the data that's out there in a way that we never could have before.

Kristi Faltorusso: All right, guys. Well now we're going to talk about this balance. So I think this is actually a great segue point to our next question here. So as we think about this, how do we want to balance automated outreach with manual high touch interactions? Because I think that there's still value in both, even in a digital scaled environment. So what do you guys think about when you're thinking about this balance between automated and what should still require manual or high touch interactions? What does that look like? Somer, why don't you get us started since you are the high touch guy on this call.

Somer Morton: It's kind of interesting. My company has had Customer Success as a function for just a little bit longer than I've been a CSM. So we are in it, and it's creating everything as it goes. And so some of our practices are not as sophisticated or even data driven necessarily. And a lot of the time it's just what's the goal that we're trying to achieve? How do we get them to achieve that goal? And it's not always scaled or even scalable.

But I just think about one example, which is where I'm a customer and I'm trying to figure out what do I have to go do in my platform in order to achieve the goal of whatever, it might be an administration task. And Rob brought up an in-app contextually dependent walkthrough that can help. And so that's a place that we're really looking at within our product, which is more contextual based support to deflect, say, support tickets, which deflects the amount of inbound increase that I might receive.

I would automate 1,000% of that to free up strategic conversations where I can look someone in the eye and ask them a really hard question and allow the silence to sit there and allow that conversation to happen so they can truly share how they're feeling. That to me is the difference, is freeing up my mental bandwidth as well to be able to sit and perform on a call, which is something we don't talk about as much is mental budget and overwhelm. And I find that those two things are really imperative because AI can't look you in the eye and have that hard conversation.

Rob Zambito: Somer, if I can jump in, I want to add to that. There was a really cool thing that I workshopped with a CSM last week. This customer was threatening to churn, threatening to write bad reviews online. They were super mad. None of us have ever seen that before.

And so we came up with a really interesting talk track, which was, scale of one to 10, 10 being 100% you're going to renew, zero being you're 100% going to leave us, where are you on that scale? And we role play that the customer says three. Three. I'm super ready to leave. Then the follow on question is, just curious, why didn't you choose two? Then what comes out of the customer is, well, you guys are the future, and you've got the integration that my last system didn't support. And I was like, that was a really cool interaction.

And if you look at the beauty of good discovery, you immediately see... A lot of us in Customer Success, we don't have CSMs ourselves, a lot of us aren't... The funny irony about Customer Success and being a CSM is that a lot of times you've never had a CSM yourself, so maybe you've never had that great discovery performed on you. Hopefully some of you have had that in therapy or something. But the cool thing is when you see discovery done super well, you're like, wow, this is night and day from the generic AI type questions.

So when I think about this problem overall, I saw a question in the chat around strictly digital motions. So usually the first pass of implementing AI for me is like, yes, you do your segmentation, like enterprise versus long tail, maybe something in between, and you develop a service model per segment. So there's definitely a segmentation solve. But then you also find ways to supplement your enterprise segment with digital motions. Digital motions shouldn't just be for that long tail. Digital motions should also be to enrich and enhance the relationships with your enterprise segment as well.

Somer Morton: I forgot the question. I just want to keep [inaudible].

Kristi Faltorusso: I was going to say something, but then Rebecca, I saw you come off mute.

Rebecca Nerad: No, it's okay. Go ahead, Kristi. Go ahead.

Kristi Faltorusso: I was just going to say one of the ways that I think about this is moments of intervention. What is being signaled to me? I think we talk a lot about AI use, the external use of it to how AI interacts with our customers. I'm just going to flip it around and say I think about the AI personalization use cases internally that signal to me moments to intervene. And that doesn't mean bad intervention. It could be something great happened, my customer did something in our solution or had some outcome. Or guess what, I was signaled from some external data that we brought in, there was, again, I think we talked about acquisition. Or people do charity work. Just anything that could feed me something that would be an appropriate moment to intervene, to build and strengthen the relationship that we have with our customers.

So that's how I think about it. It's like serving a moment of intervention that will bring value. And it could be, like I said, a milestone, an activity, an occasion, or whatever the case may be. I like to pull in all of my customers' LinkedIn profiles also and see if there is a job change and stuff like that and be able to signal and be like, oh, congratulations, or I see your hiring. Those are great moments to show that you're paying attention and I think those resonate and I think help build that trust and credibility and that relationship which ultimately builds trust.

Rebecca Nerad: I think I was looking as well through some of the questions, and one was asking about on an exec level how we connect our execs and our CSMs leverage some of that same type of info, Kristi, when we're summarizing and even if we're ghost writing to support that the leadership connect and saying this is the person. But it's when there's a change or useful information, not just we're sharing something about our release, but we heard that they did an acquisition or whatever those things are, and then we make it relevant to how we're able to help them.

I paused because there were a lot of things I was thinking of as Somer and Rob were sharing. And the one for me, you mentioned Kristi internally, it's not sexy at all, but using AI to improve our efficiency on some of the more complicated renewals, and how we look in and comparing last year. As we're working on something, a complex pricing sort of thing, we're able to do a lot more with the technology now than we ever did. And again, that drives us to be able to have the more strategic conversations instead of spending the time in the way that we used to was another example that came to mind.

Kristi Faltorusso: If anyone's ever supported a publicly traded company, and actually manually read through a 10-K report or the transcript from an earnings call, AI is a gift. I used to literally sit there with a highlighter and read these 10-K reports and try to distill them down into things that could be woven into my action plan for the customer or building relationships or thinking about my growth strategy. And now I have a prompt that I've created, and I have a GPT to process those types of things with specific objectives for those learnings and those reports.

So if you're supporting true enterprise where there is so much data and information available, I mean think about it, a publicly traded company's board of directors, if you just even entered in all their names, the amount of information that would come back, it's crazy. And so I've been using, I like the use cases for large enterprises because of all of the context that I remember very empathetically for myself having to do very manually.

Rebecca Nerad: Well, and even then, when we talk about using AI as a thought partner, and Rob was saying challenging so that you're practicing those conversations, you can even send, again, depending on the security part, but the idea of sending your board deck or your QBR deck or saying, here's the persona I'm used to working with, what questions are they going to ask? Help poke holes into this presentation. And in particular if you have recordings of past sessions, then you can even say, what will this stakeholder ask me? So that you're preparing in advance. I know again, these are the strategic examples, not the volume. But again, the way that it prepares you then, and you're much more strategic and prepared for the objections.

Kristi Faltorusso: All right. So now we've talked about all the benefits, but we obviously know that there's probably some ways that this could go terribly wrong, and let's talk about those for a minute. Because this is going to be the fun part of the conversation. So what are some of the most common pitfalls that CS orgs are going to face or face seeing when they think about scaling personalization with AI?

Somer Morton: Where do you start?

Kristi Faltorusso: Well, they get my name wrong. I'm just kidding.

Rebecca Nerad: The most common one I see is just copy, pasting, and sending. It can be a meeting summary, it can be like an AI, some email, and it's not just the name, it's just the way it's sent written without any thought to make sure that it actually is relevant to the... I mean that sounds obvious, but that you asked for the most common one, and that's the one I see most.

Kristi Faltorusso: I'm just going to jump in here and offer one before Rob and Somer are jumping in to steal all the great ideas. Governance. I just feel like, listen, Customer Success in a lot of companies, not all, lacks governance in general. And then you layer in AI, which 10x's our ability to get things really wrong for customers. And without governance over that, it's just going to amplify it. And so I think that if you don't have a program designed very intentionally around even the work that your team would do manually, amplifying that with AI is going to send things off the trail really fast. So that's my thought there is governance is probably a good place to start in terms of where it's going to go wrong.

Somer Morton: Plus one for that.

Rob Zambito: You know what was... Go ahead, Somer.

Somer Morton: Well, I was-

Rob Zambito: Oh you [inaudible].

Somer Morton: ... just going to say from... All right, I was just going to say I agree with you Kristi. And from the bottom up looking at it, there's also, which I can touch on a minute so that you can riff off Kristi, Rob, there's a cost of change for every behavioral change. Like anyone who goes to the gym, for instance, or runs is a great example. And let's say you run every day and you're good. And I come and say, "Hey, if you implement this new technique, toe running and you run every day toe running, you're going to be able to run faster." That's the potential. And so you start running toe running, and you can only run for three days because your calves are completely cooked because there's a cost of change.

And so what often happens is that it's not backed in from an enablement lens or from a sort of just thinking about the mental budget from a workflow perspective that every change incurs cost. And so there's a lot of ideas that happen, and then it's not always rolled out. There might be seven ideas at once. And so as an IC, you might see your performance dip because learning a new talk track, or you're learning a new workflow and your muscle memory's not clicking as well. So you should get a performance dip.

And so sometimes when I'm consulting leaders who are looking at implementing AI into their go-to market, amongst AEs and CSMs and stuff, we're thinking about what's their mental capacity for this quarter, and what's the upside of this AI change? If they get a 20% performance dip, is there a 30% gain so that we're net 10, or is it equal? How are we actually thinking about changing across the whole cohort? And so that's something I think is missed, given that when I ask the question, most of them say, "Oh, I've never thought about that." But there is a cost. Sorry, Rob. Go for it, bro.

Rob Zambito: No, no, that was great. That was great. It made me think about, with a lot of AI implementations, I don't think a lot of teams are taking enough time to define what success looks like with that implementation. I also think, Kristi, what you said is true. There's not a lot of folks who have stopped to define their internal charter around what, when, and how to use AI, and what tools to use. So you have a lot of CSMs having secret affairs with different tools of choice. And it's like, okay, at what point do we just pause to say we should maybe have a degree of governance around this? So I think those are two pitfalls that jumped to mind that I consistently see.

The other ones that jump to mind are hallucination and AI doing math, large language models doing math. So on the hallucination front, I've had a lot of really frustrating experiences where, like I said, I just probably spent way too much time studying behavioral science, but a lot of times these different tools are just making up studies. And it's so upsetting to me. I'm like, have some respect for the game. So the hallucination is seriously problematic at times. And it sometimes calls me Lauren for some reason. I don't know why. I don't know where it's getting some of this information from.

Kristi Faltorusso: It's because you talked about moving to Claude, so they're like, no, forget you, Lauren.

Rob Zambito: Yeah, yeah. It's not supposed to know that's my secret name. No, but anyway. The other thing is, this is a big concern for me lately is math. And when I say math, I'm specifically referring to forecasting. I have found that large language models are not the right fit in their current state to be doing forecasting. I worked for a period of time last year on a project to basically make a prediction market out of large language models. But what we consistently found, well, we found a number of barriers, one of them was that just like the AI doing the math was really not that effective and-

Kristi Faltorusso: Because it doesn't do math. Or it hasn't to date done math. It'll search the web for the things to piece it together, but it's got to be in there, but it's not doing math.

Rob Zambito: And I think part of the problem is just look at the term large language model. I'm not an expert, but I do come to realize that the unit of truth, the fundamental unit of truth for an LLM is language. And it's not necessarily, that's not always quantitative. So I'm still exploring different tools. This is also another reason why I think Claude has probably better functionality in this regard. But yeah, I don't know. I keep resorting back to spreadsheets.

Rebecca Nerad: For me, one final risk I want to call out is the risk of not leaning in and being afraid of AI and not doing anything with it at all because we're scared or because we know there's hallucinations, or maybe something didn't go well, or you weren't as successful or it took longer.

And if you're at an organization like mine where we are all leaning in, every SLT member, the third quarter of last year, we all had initiatives around it. And we're like, we're going to move fast and we're going to fail some on our way, but we are leaning in because it will make the difference in the long term. If you aren't at a company like that, it can be really scary. Because you're saying, I want to try, I've heard about this. There are experts in the area who are talking about it. But I don't know, and it might take me longer. And then there's some element that you don't trust.

And I've read some of these books around, like in the MIT study that says 95% of AI projects fail, but that's because they weren't thought out. People give up early. And so if I can say anything to this audience, it's try and try again. And you won't always get it right. So double check, stay in the loop. Don't just send and automate things right away. Get feedback. Give feedback to improve. But don't give up. The differentiator for you as someone in Customer Success, especially going forward, is how do you leverage these tools, not how you avoid them.

Somer Morton: Yeah.

Kristi Faltorusso: I love that. I think that's a great place to... Oh, sorry, Somer, go.

Somer Morton: I was just going to say we're most probably all employees here, Kristi, Rob, don't know about the audience percentage. Think about your hirability if you couldn't use a keyboard. Or now with Uber, if you can't drive a car. This is happening. It's already in. There's a cost to not changing. And as time changes, the variables of the decision change over time.

So the longer we spend planning, if you like books, there's a book called Extreme Ownership by Jocko Willink who's like an Navy SEAL. There's a clip on YouTube of him talking about the continuum of planning to action. And the longer you plan for your enemies' maneuvering. And so in the field of business, the longer it is that we plan, by the time that we spend 30 days out of our 35 days planning, the environment's changed. You don't have time to iterate. And so to riff off you, Rebecca, do what you can, and just fail repetitively really fast. Otherwise, there's a significant cost to us all for not participating.

Kristi Faltorusso: I love that. All right guys, listen, while we do have a bunch of more questions that we could potentially go through, I'm actually going to go over to the questions that our audience has asked. So just a reminder for everyone. We do go quarter past, or yeah, quarter past. No, not a quarter past. We go 15 minutes into the hour. So anyway, we're going to spend a couple minutes going through your question. So if you've asked a question, stick around, we'll likely get to it if it was upvoted. If you haven't asked a question, you want to, please go over to the Q&A, drop your question there. We are going to sort it by most upvotes. So take a minute, scan the questions there, upvote the ones that you love. For my panelists, take a sip of something, get ready. We've got some good ones here.

All right, so we're going to get started. Dawn asked, "I would love to know exactly which tools CSMs are using for AI. Is it the standard ones like ChatGPT, Claude? And how are they using it besides just refining emails and crafting messages?" I think we rattled off a couple. So why don't we just do a fast rapid fire top three AI tools that you love for CS, and no one's allowed to repeat one. Rob, go.

Rob Zambito: Can I repeat what I said before though?

Kristi Faltorusso: You can repeat what you've already said, but nobody else on this panel can repeat one that's already been said. So we are going to walk away with nine unique tool, right? Three times three. I'm like ChatGPT, I can't do math. Go.

Rob Zambito: Yeah. So for me, Spiky for sentiment analysis on calls, also transcription too, but specifically sentiment analysis, which can then feed health scoring. Quarterzip is the most advanced AI I've seen for onboarding so far. Brand new tool. But it allows context-based guidance, user guidance for users who are onboarding. And then the third, I don't know, I think I mentioned this in the chat, but Wavelength. It was called Assembly, but I think there were too many companies called Assembly. They just recently rebranded. I've been super impressed with some of the stuff that Wavelength can do. Knowing when stakeholders change. That's pretty important information when you're going into most of your critical customer interactions. Or even just like if you're sending emails to somebody who actually left their job 10 months ago, and you didn't realize. Those are the three that come to mind.

Kristi Faltorusso: All right, Somer, three.

Somer Morton: All right, I'm going to throw one, it's not an AI tool, but it's an AI function within a tool. So it's going to be in LinkedIn Sales Navigator, it can build an account profile for you. And I find that to be extremely helpful at synthesizing information around initiatives, but most importantly problems that they're having. And then looking at changes in head count so that I can adjust how I approach a customer. So that's very helpful.

Anything that's a conversational or meeting intelligence tool. I use Highspot. I used to use Gong, whatever it is. There's like a million use cases I have within Highspot. And then the last one, I'm just going to take a custom Gem ChatGPT whatever, a custom like co-pilot sidekick that understands all of your context so that you can quiz it and put information in there and accelerate how quickly you can get to that point of action when you have some kind of stumbling block or hurdle that you've come across. They're my three.

Rebecca Nerad: I am most experienced with ChatGPT where we've built agents. So ask me next time about Claude because that's what I need to go play with. But for today, my answer is ChatGPT. And again, Somer, to the point that you're saying, you can put individual... I mean I built a wine agent where I can take a picture. I know this isn't [inaudible], but where I take a picture and it tells me exactly what I've told it to tell me about the grape and where it comes from. You can make and do all the things. Yeah. Number two, Gamma, ha, ha, we didn't say that yet in part of this nine. And number three for me it's Glyphic that my team uses a lot of. And we did transition to Glyphic instead of Gong, and I'll leave it at that.

Kristi Faltorusso: All right, very good. We're going to go on to our next question. All right. Again, doing it by upvotes, guys. How are companies leveraging AI to build executive relationships between C-suites?

Rebecca Nerad: Some of that we've hit. When you think about really understanding how can you use intelligence and insights to present information to bring it back to your CSMs or to your leadership, about changes in the customer. I think that's the main thing for us. It also helps with just some of the summarizing. That sounds so, so simple, but when I think about the CSMs, just hosted a QBR, and I mean we're recording that and capturing, and what we're able to send as a summary to the leadership to explain what just happened in some of those strategic customer meetings, and then setting up the execs for follow up. I mean, it sounds obvious at this point, but that's what we primarily do.

Kristi Faltorusso: I had used AI for that specifically. So last role I was in I was CCO of our client success. So I was using it to actually drive, again, when I talked about the intervention, these moments where I was actually, of all the milestones across the customer lifecycle, there were certain that I wanted to intervene where I was reaching out to the customer specifically when certain things happened, as opposed to the CSM who might be responsible for the day-to-day.

And so I very much mapped those things out with our CSMs, and said, "I'm going to take this one, this one, and this one." And then that way it was actually a facilitator of stronger relationships because I was the one engaging and had context and an appropriate moment in time where there was a relevant outreach as opposed to an executive doing a blind outreach saying, "Hey, I just want to check in and say hi and see how things are going." Nobody cares. So an exec checking in is the same thing as a CSM checking in, it's useless, it's a waste of time, and most people won't engage. So for me it was finding appropriate triggers, and I always found that that was really helpful.

And then using AI to synthesize everything that had happened and transpired around that moment in time to drive that trigger. So I was also reaching out contextually. It wasn't like, hey, I'm reaching out because you did X, it wasn't just the activity, but it was all of the things that were happening around it too. So if they had certain support tickets open or feature requests open or CSM sentiment had had some volatility or product usage and stuff had had movement, all of the contextual signals around it were being fed to me. So that way I could use it in that conversation and also use those signals to draft the email. So it felt really relevant to the person I was connecting with.

Rob Zambito: I really like that. I feel like for me, Kristi, it actually goes back to that panel I was saying that you did... For anyone who's interested in this guy's research, I think it's really great. His name is Advait Sarkar. I think I'm saying that right.

Kristi Faltorusso: Close enough.

Rob Zambito: I'll throw it in the chat.

Kristi Faltorusso: Put it in the chat. Yep.

Rob Zambito: He and Kristi did this amazing panel last month where it was like how to use AI to challenge you. And I'm not going to lie, when I was managing accounts, I would often show up to meetings lightly prepared. And I almost took it as a point of pride. Like, oh, I could just show up to a QBR, go win a renewal, and high five my colleague and move on. But it wasn't really a point of pride. It was actually me just like sheepishly not really taking the time to prepare in the right ways.

So I would pull up a spreadsheet of customer data, and I'm like, do I really have to go through all this? But now it's like I can come into customer interactions, not just prepared with the right triggers, the right context, but also thinking three steps ahead like it's a chess match. Like, okay, the customer has this objection based on this value milestone that they were looking to achieve that I pulled from their kickoff call transcript that was nine months ago. And I'm going to prepare. I'm going to rehearse now, and I can just even do it just walking around the block. So someone with ADHD like me really benefits from that kind of thing. I can rehearse that call. So like I said before, the first time I have that conversation with the customer is not really the first time I've had that conversation. But it all depends on making sure that you're prompting your AI to challenge you in ways that might be a bit uncomfortable, and then also carving out that time in advance.

Kristi Faltorusso: All right. Very good. We're going to move on to the next question. We'll see if we can to one or two more here. So this one's from Michael for all of the panelists, what are your top three concerns or fears with using AI in your roles?

Somer Morton: I mean, eventually, I actually don't really have... Kristi, we spoke about this on our first call together ever. It was like I don't have that much fear about it, to be entirely honest because it's going to take over most of everything, and then there'll be some stuff it won't take over. I'm just going to try and ride the wave. It's disrupting everything, and that's a fact. And so then fear makes us think in binary and restrict our behavior. And so I'm actually working really hard, Michael, to not work out of a place of fear wherever possible and work out of a place of opportunity, which takes a bit of mental work, and maybe 20 minutes of free writing in my journal. But it's like accepting an inevitability that things are going to change so that I can sort of iterate from a place of creativity and excitement.

Kristi Faltorusso: I love that. I think-

Rob Zambito: I'm terrified, Somer.

Kristi Faltorusso: ... that's such a good headspace to be in. All right, I share, I'm going to do my fear, but from the context of being in my former role, so running our post-initial sales organization. My fear, because I'm thinking about AI from a senior leadership level, my fear was my team not being motivated to learn it. So for me, it's like that adoption of AI, I wanted that ingrained in the DNA of how we were thinking about solving, and I wanted people who just wanted to test and try and all that. But you can't force people to do these things. Spend all your free time. And I had half my team who was building crazy things on the weekend and other members of my team who could literally care less. So my big fear was how do you inspire and motivate people to want to creatively lean in, not be afraid of it, and figure out ways to solve problems.

Rebecca Nerad: I was going to hop on that. To me, it's really leveraging the early adopters because people are fearful. But it can't just come from me as a leader on yay AI. We have a great CSM shout out to Joe Kern who leaned in when we were starting to adopt Glyphic. And so when he was like, here's how I'm using, and asking questions.

And then we actually, he helped build out some of the workflows because he's a CSM who's using it every day and saying, here's what would be more helpful for me, and then we leverage him to help enable some of the other CSMs. So they're seeing it from Joe, Joe who knows our customers and our solutions and our challenges. And that to me was a big, it's a win for him because he obviously was curious and interested, but then more relatable for the rest of the team.

For me, my fear is, like I said, people not being mindful of what should be private. Again, there's a whole privacy thing we need to be aware of. You can't just send out your information into... When we think about what LLMs using customer sensitive data. But beyond that, if we can allow that we are in a secure place where we're allowed to share this data, to me it's how do we learn fast enough? How do we choose and prioritize probably among all the different directions in technology, how we're going in the right way. But again, some of that's just not being afraid of failing.

Rob Zambito: Can I put on my pessimist hat for a second?

Kristi Faltorusso: Let's go.

Rebecca Nerad: Please.

Kristi Faltorusso: What do you got?

Rob Zambito: I'm terrified, and I think a lot of you guys should be too. Look, I've spent this whole last hour or whatever talking about really cool tools and interesting ways to use AI. But I think if you look at a macroeconomic standpoint, so 10, 11 years ago at the first startup I was at, the founding engineers, they were Stanford AI people. And they were front row center to all the capabilities of AI like 10, 11 years ago. And now they're like, so actually two of them have spun up a nonprofit called CivAI, which is basically meant to prevent AI from taking over the world and turning us into gorillas, where we're the primate subserves of our AI overlords. I'm bastardizing a bit how they would describe their initiative and their mission.

But I don't know. I've been terrified in a way that there could be, in the near term, significant job loss. There really could be. And I don't want to scare anybody here, but this should be a motivation to stay on the bleeding edge of all the tools that are coming out there. There could be near term job loss. There could be significant near term changes to how the economics of Customer Success shake out. For example, when we're all using AI, that's not free. It actually has a cost. Every time you use AI, there's tokens being used and there's significant hardware pressure, and someone's paying for that.

And so I think it changes the economics of the CS role where we have to think about the margins of our initiatives and the tooling that we're using in a way that a lot of us hadn't before. If we stay on top of those trends, hopefully we won't become guerrilla subserves to our AI overlords. I'm exaggerating a little bit, but I do think...

Actually there is one thing that reassures me is, I was talking with a Google engineer last week, and he was like, there's a certain extent to which there are hardware limitations where AI innovation might actually start to plateau for the near term, just because there's just not enough hardware to support more innovation. Also, these things do take time. The dot com era did not take over the world in a year. It took like 20 years. So we have time to adapt. But definitely encourage everyone to stay on the cutting edge as much as possible.

Kristi Faltorusso: With the caveat saying, use your time strategically. There are so many tools out there that it could easily become a full-time job. It's funny, I'm looking at my notebook right now, I have a list of 72 tools so far of things that I should go explore. I mean, it's impossible. It would be a full-time job. So think about it strategically, and put your time where it makes the most sense because it can easily just eat all of your time.

All right, so that said, speaking of time, we are at time for today. So we have reached the end of our session. I want to thank all our guests for sharing their valuable insights, experiences. Obviously guys, your contributions made the discussion today truly meaningful for our community. To our audience, thank you for your active participation. I know that there's a bunch of questions that we didn't get to and they're good. Feel free to reach out directly to our panelists. I'm sure they'll be happy to lean in and give you a point of view on any of these.

Share your thoughts about today's session on LinkedIn. Tag SuccessCOACHING, tag SuccessHACKER. I know they love to hear the takeaways, so please go ahead and share your thoughts there. The next session will be on March 18th. These are now monthly, and they're going to be discussing how to design and operationalize handoffs between sales, onboarding, support, Customer Success, and so on, so that customers' experiences are single seamless journeys.

Finally, let me leave you with this. Great customer focused individuals know that they don't have all the answers, but they know where to find them, and that's why we've created this series. So go ahead, have a great rest of your month, and hopefully we'll see you back March 18th. Thanks, guys.

Why We Tore Down the Certification Ladder and Rebuilt from the Ground Up

What changed, why it's better, and what it means for your career or your team.

Over the last 15 years, SuccessCOACHING has trained over 39,000 Customer Success professionals across 2,000+ companies. We're ranked #1 with the highest Satisfaction score on G2 in both Customer Success Training and Training & Development. 98% of our clients rated their satisfaction at 4.6+ stars, with a 93% recommendation rate. By every traditional measure, we've been doing this well.

So why did we tear it all down?

Because the industry changed around the certification ladder, and we had to be honest about what that meant for the people relying on it.

This article will discuss:

• What NRR hides beneath the surface and why a single metric can't tell you which function broke the chain

• Why we retired the CCSM certification ladder after 15 years and what we learned from splitting a unified curriculum into two levels

• What CS Foundations is, what changed in the design, and why progressive exercises and a capstone simulation produce a fundamentally different professional

• How Core Skills Packages replace the old Levels 3-5 with capability domains that match how professional development actually works

• The new certification and recertification model, including standalone exam access, what recertification costs, and why credentials that don't evolve are souvenirs

The Ceiling We Had to Confront

In 2022, KeyBanc Capital Markets reported median SaaS Net Revenue Retention at 106%. By 2023: 102%. By 2024: 101%. Then Bain & Company published a finding that put CS in the crosshairs: 75% of companies that increased CS spending saw NRR decline.

Their conclusion was that Customer Success was failing and that post-sales teams had to evolve.

They weren't entirely wrong about the second part, but their diagnosis was overly simplistic, built on the assumption that correlation equaled causation.

The real problem wasn't that they drew the wrong conclusion. It's that they didn't cast a wide enough net. It wasn't just the post-sale teams that needed to evolve.

The real story is more complex than that. No single function is solely responsible for NRR. Blaming CS for retention outcomes is like blaming the last person who touched the ball for losing the game.

NRR as a metric requires more nuanced understanding than most leadership teams give it.

A healthy-looking number can mask serious problems underneath: new customer expansion covering for accelerating churn in mature accounts, a few large upsells offsetting a pattern of spend reductions across the rest of the portfolio, strong gross retention hiding the fact that expansion has flatlined.

Conversely, a declining number doesn't automatically point to the team managing the post-sale relationship.

NRR is the output of the entire value delivery system: how value gets identified by Marketing, communicated and committed to by Sales, and delivered and expanded by CS.

It reflects every promise made, every expectation set, and every handoff where context either transferred or evaporated. When those functions don't share a common understanding of what value means to the customer, NRR absorbs the cumulative damage without telling you where it started.

Marketing positions outcomes that sound compelling but have never been validated against what the product actually delivers in the first 90 days.

Sales translates that positioning into whatever story closes the deal, often making commitments that are technically possible but practically unachievable within the customer's constraints.

CS receives a contract, a handful of CRM notes, and a customer whose expectations were set by people now focused entirely on the next deal. The customer's first interaction with CS is a value reset.

The relationship starts with a trust deficit.

That's the pattern.

Every function hits its own numbers. Marketing hits MQLs. Sales hits new ARR. CS hits activity metrics.

And NRR keeps falling, because nobody is measuring whether value is actually flowing consistently from one function to the next.

When every department's dashboard is green, nobody looks for a system problem.

The missing piece is a shared methodology for identifying and communicating customer value that connects every function so the handoffs stop destroying the very thing that drives retention.

That understanding is what forced us to rethink not just our curriculum, but our entire approach as we needed to not only enable CS, we needed to enable a series of functional areas to operate as a single entity.

We'll be publishing a separate post that goes deep on the full cross-functional value delivery challenge and how we're addressing it across Marketing, Sales, and CS with a unified methodology. But the part that matters for CS professionals right now is this: even the best-trained CSM in the world has a ceiling when the value gap was created before they ever met the customer. And CS training that doesn't equip people to identify, articulate, and prove value in business terms that connect to what was promised upstream isn't just incomplete. It's building capability that stops short of where the profession actually needs it.

That ceiling forced us to ask a hard question: if CS training alone can't solve the retention problem, what does CS training need to become?

The answer had two parts.

First, we needed to infuse a systematic value identification and communication methodology into the CS curriculum itself, so that CS professionals have the tools to not just deliver value but to trace breakdowns back to their source and make a credible, data-backed case for systemic change.

Second, we needed to extend that same methodology to Marketing and Sales so that the upstream handoffs stop creating the problems CS has been absorbing. The first part is CS Foundations. The second part is coming in our next post.

But it all started with fixing what we'd gotten wrong in our own curriculum.

Why CS Foundations Replaces CCSM Levels 1 & 2

The original SuccessCOACHING curriculum was designed as a single integrated program. Discovery through expansion. Mindset through methodology. One connected system where every skill reinforced every other skill, because that's how Customer Success actually works.

We split it into two levels for one reason: time commitment. A 24-week program is a significant ask for busy CS teams managing live customer portfolios. Breaking it into two levels reduced the upfront commitment and made it easier to get started.

That was the right instinct. But it had an unintended consequence.

When you divide a single integrated curriculum into two levels, you create a hierarchy that tells organizations certain skills are foundational and others are "next-level." The skills that ended up in Level 2 were the ones most directly tied to revenue: health scoring, risk management, business reviews, retention and renewal execution, expansion methodology.

These aren't advanced skills. They're essential capabilities that every CSM needs from the moment they're managing a customer portfolio.

But the two-level structure gave organizations a natural stopping point right before the revenue-critical content. "Complete Level 1 first, evaluate Level 2 next quarter." That next quarter often became next year, not because anyone failed, but because the structure provided permission to defer.

CS Foundations restores the original intent. One integrated program, 18 courses, complete lifecycle coverage, no hierarchy. And we solved the time commitment problem through better instructional design rather than by splitting the curriculum apart.

What Actually Changed

The critical addition: progressive exercises that build on each other across the entire program, culminating in a capstone simulation.

When the curriculum was split, exercises were self-contained within each course. In CS Foundations, each exercise extends the work from the previous one, so by the time a CSM reaches retention and expansion, they've built an integrated body of work that demonstrates how discovery, success planning, relationship management, health scoring, and risk management connect as a unified system.

The capstone was only possible because the curriculum was reunified. There was no point in the two-level structure where a learner had completed the full lifecycle and could be assessed on integrated capability. CS Foundations creates that point, and uses it.

Before CS Foundations, a CSM walks into a renewal conversation and improvises a value narrative from whatever data they can find. They run business reviews that customers tolerate. They spot risk when a customer stops responding, which is too late. They know expansion matters but don't have a methodology for connecting achieved value to unrealized potential in a way that feels like guidance rather than a sales pitch.

After CS Foundations, that same CSM walks into the renewal with a value realization framework they've been building since discovery, where the business case for renewal was constructed progressively, not assembled the night before. Their business reviews become working sessions customers actually want because they're organized around the customer's outcomes, not the vendor's metrics. They see risk in health score patterns weeks before it becomes silence. And they surface expansion opportunities by connecting what's already been achieved to what's possible next, in the customer's language, tied to the customer's goals.

Same person. Completely different professional.

And here's what that looks like in practice beyond individual CS performance: a CS team with this methodology stops relying on anecdotes to describe upstream problems. They produce data. They trace churn to specific expectation gaps set during sales. They quantify the revenue impact of positioning that doesn't match deliverable outcomes. They walk it back through pipeline sources, win/loss patterns, and deal velocity by segment, and connect it to retention outcomes in a way that builds a case every CEO and CFO should listen to.

CS sees how the entire value delivery system shakes out. That's not a limitation. It's a strategic advantage, and it's how CS stops being seen as shifting blame and starts being seen as an agent of change.

Core Skills Replace Levels 3-5

The old CCSM Levels 3 through 5 assumed everyone needs to climb the same rungs in the same order. That's not how professional development works. A CSM managing enterprise accounts needs stakeholder influence and executive engagement. A CSM promoted to lead a team needs segmentation strategy and capacity modeling. The ladder forced everyone through the same progression regardless of role, experience, or immediate needs.

The new model organizes the same expertise, and significantly more of it, into eight capability domains with 66+ courses. Customer Value & Business Acumen. Interactions & Trust. Problem Solving & Critical Thinking. Execution & Operating Rhythm. Health & Risk. Stakeholders & Influence. Storytelling & Communication. Personal Performance & Career Growth.

Purchasable as complete packages or individual courses. No gates, no prerequisites, no prescribed sequence. Build into what you need based on where you are and where you're going.

Certification and Exam Model

CS Foundations Certification tests applied methodology, not memorized content. The exam is aligned with the capstone simulation model where you demonstrate integrated capability across the complete lifecycle.

Already have the skills? The CSF Certification Exam is available standalone at $199. One attempt plus one retake. Pass and you're certified without the program. Don't pass on the second attempt, and your $199 is credited toward the CS Foundations program price.

Recertification is new, and it matters. The CS discipline doesn't stand still. Revenue targets, AI-augmented workflows, cross-functional accountability. A certification that validates a moment in time but never asks whether you've kept pace isn't a professional credential. It's a souvenir. Recertification happens every two years via exam. No requirement to retake the program. Pre-purchase at enrollment for $99, which also extends your access to the complete course materials and all updates until your certification expiration date.

Additional certification levels are coming, organized around capability domains rather than sequential tiers. They'll validate demonstrable expertise in specific capability areas, not content completion. Details soon.

Pricing

CS Foundations: $595 for the complete 18-course integrated program with progressive exercises and capstone simulation.

CSF Certification Exam (standalone): $199. One attempt plus one retake. Credited toward program price if you need it.

Recertification (pre-purchase at enrollment): $99. Includes extended course material access through certification expiration.

Core Skills: Varies by package and individual course selection.

Why This Matters Right Now

The profession is splitting, and the data is unambiguous about which direction it's going. Companies are eliminating tactical CS roles (44.2% report layoffs) while paying $175,000-$200,000 for strategic CSMs with proven methodology. Gartner predicts half the companies that cut CS staff will rehire by 2027, but for systematic capability, not relationship management.

The question isn't whether you're good at your job. It's whether you have the methodology to prove it. To walk into a renewal with a business case built on demonstrated value, to run a business review your VP actually wants to attend, to surface expansion in terms your customer's CFO cares about, and to do all of it systematically rather than through intuition and effort alone. That's the difference between the CSMs getting laid off and the CSMs writing their own job descriptions.

For CS leaders: you already know that training your team harder on the same things isn't moving NRR. You've felt the ceiling. CS Foundations gives your team the methodological core to prove value in business terms, and more importantly, to produce the data that makes a credible case for fixing the upstream problems you've been trying to articulate for years.

What Comes Next

CS Foundations is the first part of the answer. The second part, extending the same value methodology to Marketing and Sales through Identifying & Communicating Value (IACV) and Value-Based Selling (VBS), is what closes the loop. We'll cover the full Revenue Team enablement offering in a follow-on post.

But it starts here, because CS is where the entire value delivery system either proves itself or falls apart. And it starts with your team having the methodology to do both: deliver value systematically and prove it in terms the business can act on.

Frequently Asked Questions

What is Revenue Team enablement?

Revenue Team enablement is a training and methodology approach that aligns Marketing, Sales, Customer Success, and Customer Support around a shared framework for identifying and communicating customer value. Unlike traditional department-specific training, it addresses the cross-functional handoff failures that cause Net Revenue Retention to decline, even when individual departments perform well by their own metrics.

Why doesn't increasing Customer Success spending improve NRR?

Because most of that spending doesn't go to enablement. Companies buy CS management software, add headcount, change strategy, and redesign processes, but they never equip the people doing the work with a shared methodology for identifying and communicating customer value. They optimize inside the CS silo while the real problem starts upstream: Marketing sets expectations the product can't deliver, Sales makes commitments CS can't execute, and the customer arrives with a value gap that more headcount and better software can't close. Bain & Company found that 75% of companies that increased CS spending saw NRR decline, because the investment attacked the symptoms while leaving the fragmented value delivery system that produces them completely intact.

What is IACV (Identifying & Communicating Value)?

IACV is a course that establishes a shared methodology for how every customer-facing function identifies what value means from the customer's perspective and communicates it without distortion. It serves as the connective tissue across the Revenue Team, ensuring that what Marketing positions, Sales sells, and CS delivers are the same thing. IACV is available as a standalone course ($99) and is also encompassed within Value-Based Selling.

What is Value-Based Selling (VBS)?

Value-Based Selling is SuccessCOACHING's sales enablement program that teaches outcome-based discovery, value narrative development, stakeholder influence, negotiation, and expansion strategy. VBS encompasses IACV and extends it with the complete methodology for selling on value rather than features or price, while ensuring that what's sold is what CS can deliver. It's designed for Sales teams ($795) and increasingly for CS professionals who carry revenue and expansion targets.

What is CS Foundations?

CS Foundations is an 18-course integrated program covering the complete Customer Success lifecycle from discovery through expansion. It replaces the former CCSM Level 1 and Level 2 certifications by reunifying the curriculum into one program with progressive exercises that build on each other and a capstone simulation that assesses integrated capability. CS Foundations is CPD Service accredited and developed in partnership with the University of San Francisco's School of Management.

What happened to CCSM Levels 1 through 5?

CCSM Levels 1 and 2 have been replaced by CS Foundations, which restores the original integrated curriculum design. The split into two levels created an unintended hierarchy that gave organizations a natural stopping point before the revenue-critical content. Levels 3 through 5 have been reorganized into Core Skills Packages and a Core Skills Library. The same expertise (and more), organized by capability domain rather than sequential levels, so professionals can build into what they need based on role and growth trajectory rather than climbing a prescribed ladder.

Can I take the CS Foundations certification exam without completing the program?

Yes. The CSF Certification Exam is available as a standalone option at $199. You receive one attempt and one retake. If you pass, you're certified without purchasing the program. If you don't pass on the second attempt, you'll need to complete CS Foundations before sitting the exam again, and your $199 exam purchase is credited toward the program price.

How does recertification work?

Recertification is a new program launching alongside CS Foundations. Certified professionals recertify every two years via exam. No requirement to retake the program. This ensures that your certification reflects current capability, not a historical achievement. Students can pre-purchase recertification for $99 at the time of their original enrollment, which also extends access to the complete course materials and all updates until the certification expiration date, an additional two years of access to an evolving curriculum.

Will there be certification levels beyond CS Foundations?

Yes. The former CCSM Level 3, Level 4, and Level 5 certifications were organized as sequential rungs on a ladder, each one certifying that you completed the next tier of content. The new certification levels being developed replace that approach entirely. They'll be organized around the capability domain architecture, validating demonstrable expertise in specific capability areas rather than simply certifying that more content was completed. Details will be announced soon, but the principle is consistent with the CS Foundations redesign: certifications should measure what you can do, not what you sat through.

Customer centricity isn’t a new concept. But recently, this framework has grown more important for both business outcomes and customer satisfaction. In a market where budgets are shrinking, expectations are high, and customers can churn on a dime, it’s customer centricity that can be a key competitive differentiator. 

But creating a truly customer-centric organization requires more than just slogans and mission statements: it requires full buy-in from each function, from Sales to Marketing. And while each business unit plays a role in customer centricity, Customer Support is uniquely positioned to move the needle in delivering a superior customer-centric experience, given its regular contact with customers who need help resolving issues.

Why? When Customer Support professionals are equipped with the right skills, context, and confidence, they don’t just quickly close tickets – they reinforce customer trust, uncover expansion revenue opportunities, and become strategic partners. 

So, which skills can help Support reps accomplish these goals? Customer Success principles, which, as it turns out, are the missing link in many customer experience initiatives. 

Here’s why Customer Support teams should become customer-centric, and why Customer Support team training (which incorporates CS principles) is your secret weapon.

This article discusses: 

• Beyond lip service: What real customer-centricity looks like.

• The front lines: why Support teams are critical to customer experience.

• Knowledge gaps: what most Support teams don’t know about Customer Success.

• Structured training vs. on-the-job learning: the case for formal programs.

• Creating alignment: how support training affects other departments.

• Implementation strategy: starting with CCSS certification.

• Long-term impact: how transformed Support teams change organizational culture

Beyond Lip Service: What Real Customer-Centricity Looks Like

To understand why Customer Support team training is essential for building a customer-centric organization, we first need to define what customer-centricity means.

It’s easy for organizations to say “we put customers first.” But for too many companies, customer-centricity stops at mission statements and slide decks. Real, tangible customer-centricity goes beyond what is said, and shows up in how decisions are made, how teams are measured, and how employees are empowered. 

When organizations fully adopt customer-centric business models, both businesses and their customers can feel the benefits. Research shows that customer centricity can lead to significant gains in key metrics such as sales growth, customer loyalty, net profit, and customer confidence, and further data indicates that customer-centric businesses are 60% more profitable than non-customer-centric businesses.

Here’s what customer centricity actually looks like:

1. Customer impact is a main KPI: Measurements like customer satisfaction, retention, and customer lifetime value are key metrics that are tracked, reported, and tied to performance across teams.

2. Frontline teams are key: Customer-facing functions (such as Customer Support and Customer Success) have a seat at the table, helping shape strategy and ideas. Their feedback about what customers need, desire, and are lacking help inform everything from product design to go-to-market strategies. 

3. Feedback loops are built in: Customer feedback isn’t something that’s haphazardly collected and forgotten. In a customer-centric business model, feedback is shared, analyzed, and acted upon. When a customer points out friction or confusion, teams don’t just fix issues: they aim to prevent them from happening again.

4. Emphasis on long-term outcomes: Real customer-centric companies focus on playing the long game rather than short-term wins. For example, they’ll avoid overpromising to close a deal or prioritizing efficiency at the cost of experience. Instead, they focus on building trust and loyalty. 

Customer-centricity isn’t a label or a buzzword: it shows up in everyday actions, cross-functional collaboration, and a culture that prioritizes doing what’s right for the customer.

The Front Lines: Why Support Teams Are Critical to Customer Experience

Customer-centricity is an organization-wide effort. But when customers think about your company, they’re not thinking about your internal org chart; they’re thinking about the experiences they have. And in many cases, Support reps are the front-line team members who actually make contact with your customers. 

Consider this: Support reps are the first to hear when something breaks, when expectations aren’t met, or when a customer simply needs help. In those moments, Support doesn’t just fix problems (although that’s a big part of what they do). They influence customer perceptions, build trust, and directly impact whether a customer stays or churns. 

Here’s why Support teams are so vital to delivering a customer-centric experience:

1. They Hear (Unfiltered) Customer Sentiment

Support reps regularly get a real-time pulse on customer frustrations, needs, and desires, oftentimes long before those insights make it into a formal feedback survey or report. This allows Support teams to surface (and address) pain points and identify patterns that other teams might not ever see.

2. They Influence Customer Emotion

When customers are frustrated, confused, or under pressure, Support can be their lifeline. A fast, effective, empathetic response can turn a negative moment into a brand loyalty win, while a poor response can undo months of relationship-building.

3. They Drive Retention and Expansions

Support interactions are key touchpoints in the customer journey, and can vastly influence retention and expansion decisions. Keep in mind, data shows more than half of customers will churn to a competitor after just one unsatisfactory customer experience. Beyond that, Support reps can also be notable drivers of expansion by offering tactful suggestions on features or service tiers that might be useful to customers.

4. They Inform Tactics, Products, and Strategies

Customer Support reps have the opportunity to drive meaningful change within their organizations that benefits customers. When reps are empowered and trained to obtain insights, they can use feedback to inform product changes, feature launches, marketing campaigns, and sales strategies, so that they’re better tailored for what customers really want (and need).

In short, Customer Support plays a critical role in shaping the customer experience. But to curate a meaningful and positive customer experience, Support reps need to be trained in Customer Success principles, which allows them to go beyond mere ticket resolution. 

Knowledge Gaps: What Most Support Teams Don't Know About Customer Success

Customer Success and Customer Support both aim to help customers, but the way they approach that goal is like two sides of the same coin. But for Support teams to drive customer-centricity with Customer Success principles, they first need to be clear on what these principles are.

Here’s what you might (or might not) know about Customer Success.

• Success is about achieving outcomes: While Support teams are trained to close tickets, Success teams are focused on whether customers are reaching their long-term goals. When Support starts tailoring their interactions around those goals, they can resolve issues in ways that reinforce progress (instead of just providing temporary fixes).

• Success teams map the entire customer journey: Support teams operate in the moment, handling isolated issues. But Customer Success teams work across the entire customer lifecycle, from onboarding to renewal. Understanding this journey helps Support agents tailor their tone, urgency, and guidance.

• Success relies on strategic conversations: Support is often reactive and technical. But with Success principles, Support agents can be proactive, strategic, and consultative.

• Success can spot cross-sell and upsell opportunities: Customer Success Managers are pros at recognizing revenue signals and driving expansion conversations. Support reps can develop the ability to read between the lines during customer interactions and suggest expansions that are actually useful to customers. 

By bridging these knowledge gaps, Customer Support teams can move from single-ticket problem-solvers to proactive partners who help drive retention, expansion, and loyalty at scale. 

Structured Training vs. On-the-Job Learning: The Case for Formal Programs

When it comes to choosing Support team training, it’s possible to learn through both formal and informal methods. Many Support reps learn by doing – shadowing peers, troubleshooting in real-time, and figuring things out on-the-fly. While hands-on experience is valuable, it’s usually not a substitute for structured, intentional training. In fact, relying solely on on-the-job learning can lead to inconsistent service, knowledge gaps, and missed opportunities to truly deliver customer value. 

Why exactly? First, let’s consider consistency. Without structured training, each rep develops their own way of handling tickets, leading to wildly different experiences for customers. Formal programs create standardized skills and processes, ensuring customers get consistent, high-quality service every time.

Next, on-the-job learning can be random, with agents only learning what they encounter. On the other hand, formal training ensures everyone is taught the full range of skills, systems, and customer scenarios they need to succeed, including how to think strategically rather than just react tactically. 

Importantly, with structured training, learning doesn’t stop after onboarding. Instead, continuous learning becomes part of the culture. Ongoing training, coaching, workshops, and skill refreshers keep Support teams smart and adaptable. Data shows that organizations that emphasize continuous learning are 92% more likely to innovate, and that they’re more profitable, deliver higher-quality work, and more likely to have the skills they need for the future.

Creating Alignment: How Support Training Affects Other Departments

Support team training isn’t just an investment in one department: it’s a catalyst for top-tier cross-functional alignment. Why exactly? When Support is trained in Customer Success principles, reps become a bridge between customers and the rest of the organization by delivering insights, reducing friction, and helping teams work together to create a customer-centric environment.

For example, consider the Product team. Support teams trained with Customer Success principles don’t just report bugs – they take corrective action, like translating customer insights into actionable product insights. With their ability to identify patterns, gauge sentiment, and articulate feature gaps, Support teams can help Product teams take customer feedback into account for roadmaps and rollouts.

Support can similarly impact marketing. Think about it: Support hears firsthand when customers have misaligned expectations (which can stem from inaccurate marketing messaging). Instead of simply ignoring the “bigger picture,” Support teams trained in CS practices capture and communicate that feedback, so marketing gains clarity on which messages resonate and which need to be adjusted.

Well-trained Support teams can also use their understanding of the full customer journey to provide context-rich handoffs and insights to Sales and Customer Success teams. This reduces repetition for customers and creates a seamless, coordinated experience that builds credibility from Day One.

Implementation Strategy: Starting with CCSS Certification

If you’re serious about building a customer-centric organization, you’ll need to lean on your Support reps to get there. But it’s likely the case that their current skills aren’t enough to drive the outcomes you’re looking for. To achieve these strategic results, your Support team needs to adopt Customer Success principles. That’s where the Certified Customer Support Specialist (CCSS) training program comes into play. It’s designed to transform your Support function into a strategic growth driver through the use of Customer Success skills. 

This training program equips reps with the consultative problem-solving and relationship-building skills they need to turn everyday Support interactions into business-growth opportunities. This proven 12-course curriculum transforms reps from reactive problem-solvers to proactive business contributors. 

Ultimately, when you use formal Support training to upskill your team with CS principles, you reposition your reps from ticket-closers to customer champions (who have tools to create meaningful impact).

Long-term Impact: How Transformed Support Teams Change Organizational Culture

Launching the right Support team training does more than improve metrics: it can reshape the DNA of your organization. Why? Support reps can use their newfound abilities to inspire significant shifts in organizational culture. 

Here’s how transformed Support teams trigger ripple effects that create lasting cultural change:

• Customer-centricity becomes a company-wide mindset: When Support leads with emotional intelligence, empathy, and a deep understanding of customer goals, other teams can follow. For example, Product might start asking, “How will this feature help the customer succeed?” while Sales begins to frame their pitch in terms of value rather than features.

• Silos break down around shared goals: A strategically trained Support team speaks the same language as Customer Success, Product, and Marketing. This shared understanding fosters better handoffs, more collaboration, and a unified focus on helping customers reach their goals. 

• The customer experience becomes a competitive advantage: As Support teams positively impact the customer experience, the entire organization begins to benefit. Over time, it becomes a competitive advantage, where your organization provides a collectively excellent customer experience, which fosters stronger retention, higher lifetime value, and a brand customers trust.
  
  

In the long run, investing in CS-informed Support training does more than elevate just a single team. It sparks a cultural shift in which customer-centricity is everyone’s responsibility and where every team member plays a role in customer outcomes.

Frequently Asked Questions About Training Support in CS Principles

Why should Customer Support teams learn Customer Success principles? 

Support teams trained in Customer Success principles move beyond reactive ticket resolution to become strategic partners who reinforce customer trust, identify expansion opportunities, and drive retention—directly impacting business outcomes like customer lifetime value and satisfaction scores.

How does training Support teams in CS principles impact revenue? 

Support reps trained in Customer Success principles learn to recognize revenue signals and cross-sell opportunities during everyday interactions, turning routine support conversations into expansion drivers; research shows customer-centric businesses are 60% more profitable than their counterparts, and trained teams can identify 25-30% more expansion opportunities while achieving higher conversion rates.

What's the difference between Customer Support and Customer Success approaches? 

Customer Support traditionally focuses on resolving isolated issues in the moment, while Customer Success takes a proactive, lifecycle-wide approach to helping customers achieve long-term outcomes. When Support teams understand this distinction, they can tailor interactions to reinforce customer progress rather than just provide temporary fixes.

How does Support team training impact other departments? 

Well-trained Support teams become bridges between customers and the rest of the organization by translating customer insights into actionable feedback for Product, identifying messaging misalignments for Marketing, and providing context-rich handoffs to Sales and Customer Success teams.

What is the CCSS Certification, and how does it help Support teams? 

The Certified Customer Support Specialist (CCSS) program is a 12-course curriculum that equips Support reps with consultative problem-solving and relationship-building skills, transforming them from reactive ticket-closers into proactive customer champions who can turn everyday interactions into business-growth opportunities.

CS Mastermind #81 Transcript: Customer Health Scores and Predictive Analytics: Using Data to Get Ahead

Customer health scores and predictive analytics are essential tools for CSMs who want to move from reacting to problems to preventing them. By combining product usage data, sentiment signals, engagement activity, and historical trends, health scores give Customer Success professionals a clear, data-driven view of which accounts are thriving, which are at risk, and where to focus their time.

In a world where portfolios are growing and expectations are rising, data becomes your advantage. Customers expect personalized, proactive guidance, and companies expect CS teams to deliver measurable results. Health scoring and predictive insights allow CSMs to work smarter, not harder: streamlining workflows, improving customer experiences, and driving better outcomes.

In this CS Mastermind session, hosted by Andrew Marks and Kristi Faltorusso, our panelists discussed:

• How predictive analytics help identify early indications of churn

• The tools, platforms, and data points helpful for uncovering expansion opportunities

• Balancing quantitative data with qualitative signals

• Common mistakes when building or interpreting health scores

• Using health score data to prioritize workflows

• Effectively communicating health score insights

This webcast featured:

• Ariel Benzakein, Founder & Principal Consultant at RetentionForge

• Krista Roberts, Director, Success Services at ClientSuccess

• Rachel Jennings-Keane, Principal Customer Success Manager at People.ai

Top Takeaways:  

1. Design more useful health scores by focusing on outcome-based indicators instead of activity data. Start by analyzing 10-20 recently churned customers to identify predictive signals of renewal risk. Rather than relying on activity-based metrics, health scores should measure progress toward customer value realization to more accurately predict renewal risk.

2. Monitor leading indicators that can be influenced before renewal risk appears. Measuring early milestones, such as pre-training content completion or feature adoption momentum, provides opportunities for proactive intervention before problems manifest in renewal risk. This enables CS professionals to take preventive action instead of simply documenting what has already occurred.

3. Validate health scores against actual churn data before rolling them out. Backtesting proposed health scoring models reveals whether the selected metrics actually correlate with risk. This prevents teams from wasting time chasing misleading signals that don't predict actual customer outcomes.

4. View health scores as tools for visibility and prioritization, not replacements for relationship management. Health scores help leaders identify patterns across portfolios and spot risk at scale, while individual CSMs should maintain direct customer relationships that surface nuanced issues data cannot detect. Predictive analytics are most effective when automated signals are paired with human insight and context.

5. Apply different health scoring methodologies by customer segment rather than relying on a one-size-fits-all model. Strategic accounts and tech-touch customers require distinct indicators that reflect their engagement and value realization patterns. Segment-specific health scores keep predictive metrics relevant and actionable across the customer base.

Session Replay

Session Transcript

NOTE: The following transcript has been edited for clarity and content where necessary to improve readability.

Andrew Marks: Welcome, everyone, and thanks for joining us. I'm Andrew Marks, co-founder of SuccessHACKER and architect of the SuccessCOACHING Training Program. You're joining us for our newly-evolved CS Mastermind, a single monthly conversation designed for both Customer Success leaders and individual contributors.

This series is brought to you by SuccessCOACHING, where we've helped more than 40,000 customer-facing professionals across 96 countries build the skills they need to deliver real, measurable value to customers. Whether you're leading a CS organization, managing accounts, supporting customers, or sitting somewhere in between, our goal is simple, help you do work that actually matters. You can find details on all of our programs at successcoaching.co, and Ashli is about to drop links and any offers we're running into chat.

Before we get into today's topic, I want to take a minute to explain what's changed and why. Historically, we ran two separate monthly webcasts, one focused on leadership topics and one designed specifically for practitioners, but over time and based on a lot of feedback from this community, it became clear that the line between leader challenges and IC challenges isn't nearly as clean as we once thought. The best individual contributors think strategically. The best leaders stay close to the work. So instead of splitting those perspectives apart, we're bringing them together.

And going forward, CS Mastermind will be one shared conversation where leaders can think more tactically, practitioners can think more strategically, and we can all benefit from hearing how different roles experience the same challenges from different angles.

Every session will be designed to deliver practical insight you can apply immediately, strategic context for why the work matters, and honest conversations that challenge some of the best practices we've all inherited.

Before we move on, I want to share a quick piece of context, just something personal that's been on my mind lately. As some of you who follow me may have read on LinkedIn, I lost my father on New Year's Eve. I'm not going to get into the details, but there's one thing he used to say to me all the time, growing up. He absolutely loved this line and he said it so often that it basically burned into my brain. Half of being smart is knowing what you're not smart at. At the time, I mostly rolled my eyes. And as it turns out, he was right. Over the years, that idea has shaped how I think about leadership, about Customer Success, and honestly about how I've tried to build my own career. And it's a big reason this series exists, and it actually underpins how we've built SuccessHACKER and the SuccessCOACHING Training Program. We don't believe great professionals succeed because they have all the answers. They succeed because they know where they're strong, where they're not, and when to learn from people who see the world differently than they do.

CS Mastermind was built to create that kind of space, which brings me to the next evolution of this series. I'm excited to welcome Kristi Faltorusso as my co-host for CS Mastermind. Kristi is a colleague, a longtime friend, and one of the most respected voices in the Customer Success community. She brings a practitioner's mindset, a leader's perspective, and a very real worldview of what actually works.

Some months, Kristi and I will host together. Other months, one of us may be flying solo, but regardless of who's on the screen, the intent stays the same. Thoughtful moderation, meaningful dialogue, and conversations that go beyond surface-level advice.

And if you follow Kristi's work, you already know she doesn't shy away from nuance or uncomfortable truth. I don't think shy is in her lexicon, and that's exactly why I'm excited to build this series together. So welcome, Kristi, and thank you for joining me on this ride.

Kristi Faltorusso: I'm so excited to be here. Obviously, we've partnered a lot over the past couple years. So to make it a bit more formal, to come together this way at this time, when you're bringing these sessions together, I'm super excited about it. So I'm grateful for you, for Todd, and for the community for giving me this opportunity.

Andrew Marks: Awesome. And we are of you. A few quick housekeeping notes before we begin. This session is being recorded, and the replay and transcript will be shared next week. Please use the Q&A feature for questions. The most upvoted ones will get priority. Use the chat for commentary and reactions. For LinkedIn Live viewers, you can post questions directly in the comments, which will be relayed to us.

Now I'm excited to introduce today's panel. As always, I'll let our guests introduce themselves to y'all in alphabetical order so you can hear directly about their backgrounds and perspectives. So let's get started with Ariel.

Ariel Benzakein: Yeah. I mean, as AB, I always get to go first on these, so that's great. So I'm Ariel. I'm the Founder of RetentionForge, which is a consulting company that helps SaaS businesses grow their GRR, NRR, and evaluate why you have churn reasons and fix them. So if your GRR is not 94 plus and your NRR is not 115 plus, we can help you get there.

Before that, I have 25 years of experience leading all of the post-Sale customer-facing teams at software companies. I've worked at some big places like Experian, Donnelley Financial, PerkinElmer, as well as a bunch of startups. So really pleased to be here today. This is a great panel.

Just one other thing real quick. I'm having work done on my house, so if you hear some noise, I will mute myself. Thanks.

Andrew Marks: Awesome. Thank you, sir. Next up is Krista.

Krista Roberts: Hi, everyone. Excited to be back. These are some of my favorite webinars to be on. So I'm Krista Roberts. I am currently the Director of Success Services at ClientSuccess. I've spent over a decade in the Customer Success world, working across various SaaS organizations in both leadership roles and as individual contributor. So I've really seen the CS space from every angle, and in this particular topic from every angle as well. I've built teams, led teams, partnered closely with customers, really focused most recently on creating and reinventing onboarding, also managing retention, and really trying to make things scalable and all that fun stuff that we do. And so just super excited to be here to contribute to this chat on customer health scores today, and excited for the rest of the panel and for Kristi.

Andrew Marks: Awesome. And finally, Rachel.

Rachel Jennings-Keane: Hi, everyone. I'm Rachel Jennings-Keane. I'm a Principal Customer Success Manager at People.ai currently, but I've been in Customer Success for over 10 years, both in an IC role and leading a team. I've had several iterations of building a health score, what should go into it, all of that. So excited for this discussion today, and looking forward to us diving in.

Andrew Marks: Awesome. Thanks for joining us, Rachel, from across the pond. Kristi, I don't know if you want to ... By the way, folks, Kristi and I are still figuring this out. So Kristi, I don't know if you want to mention to people what you're doing now or any of that stuff before we get started?

Kristi Faltorusso: No, not yet. Nope. Not today.

Andrew Marks: Okay. All right.

Krista Roberts: Today, this is what she's doing today, Andrew.

Kristi Faltorusso: Today, this is my priority.

Andrew Marks: Oh, I like that. That's great.

Krista Roberts: He likes to keep us all on our toes.

Andrew Marks: Yeah, yeah. Yeah.

Kristi Faltorusso: Soon. Soon. Soon. Not today, though.

Andrew Marks: Awesome. Awesome. All right. Thank you all for being here and for making the time to share your experiences with this community. So today, we're talking about customer health scores and predictive analytics. And I'm going to start by saying something that might be a little uncomfortable, which has been a trend for me for the last, I don't know, 18 to 24 months on this webinar series. I think that most customer health scores are theater. They look good in QBRs. They make executives feel like we have our finger on the pulse. They give us something quantifiable to point to when leadership asks how our customers are doing.

But here's the problem. How many of us have had a customer churn that was green in the system the week before? How many of us have seen an at-risk customer renew and expand because someone actually picked up the phone and had a real conversation?

We've built an entire industry around the idea that if we just get the right combination of product usage metrics, NPS scores, Support tickets, and engagement data, we can predict the future, but customers aren't algorithms. They're people making decisions based on budgets, politics, competing priorities, and relationships, things that don't always show up in the dashboard of a CSP or CRM system.

Now, I'm not saying that health scores are useless. I'm saying we might be over-indexing on the score and under-indexing on the judgment, intuition, and the relationship intelligence that actually saves and grows accounts. I've always said it's not about what's happened, it's about what you're doing now.

So today, I want to challenge our panelists and all of you to think critically about how we're using these tools. Are they making us better at our jobs or are they giving us a false confidence while we miss what's really happening with our customers?

So here's my challenge to the panel, and I've got a bunch of zingers to throw at you as you go through this. Defend the health score. Tell me why I'm wrong or tell me where I'm right and what we should do about it. And I just realized we didn't decide who was going to talk first like I normally do. So who wants to jump in on this first? Ariel, it's all you.

Ariel Benzakein: Yeah. So because I'm AB, I get to go first again.

Andrew Marks: I don't think ... All right. Whatever. Whatever makes you happy.

Ariel Benzakein: I love this question, Andrew, because it's forcing us to defend something that fails most of the time at most companies, from what I've seen. So I'm not going to try to say that every health score is valuable. I think most of them actually are theater, but what I'd push back on a little bit is that the problem isn't the concept of a health score. It's the execution.

So I think there's really three or four reasons why they're theater. So one of the main ones is that they're built backwards. So when a team is building a health score, they'll start by saying, "What data do we have," instead of the more important question, which is, "What causes customers to churn?" So what they'll do is they'll throw 30 attributes into a dashboard, half of them don't predict anything. That's not a health score. That's just noise integrated into your Salesforce or your CSP. I can give you three more if you want, but I'll stop there.

Andrew Marks: Did you know that there was a survey that found that not only do just 7% of companies regularly monitor health scores, but 50% of companies don't track it at all?

Ariel Benzakein: Yeah, I'm not surprised. When I've inherited teams, 90% of the time I would inherit one where they had no working health scores. So something is in there and the team is just not using it. They're ignoring it. So why have it? And then the other half or the other 10% is exactly what you're describing. There's no health score.

Rachel Jennings-Keane: I'd be curious to understand from everyone that's joining the webinar who has a health score that they actually use and rely on today, because I think I've had that experience of ... I've inherited a team, there's a health score, nobody trusts the health score. It's using data that's no longer relevant for the time that we live in, especially now. I feel like that's accelerated a lot. The old way of health scoring, I think, is going out the window faster than we know and believe in this AI era especially, and I think we just need to be a lot smarter in the way that we approach health scores.

I think the intuition piece, Andrew, as you're saying, is really key, but how do you build that into a health scoring model? That's, I think, one of the things that everyone gets stuck on, and then you're spending a lot of time on that rather than just getting something and starting to measure it to see ... Does this actually make sense for our business?

A health score is unreliable and no one trusts it. That's what I find most of the time. Yeah.

Krista Roberts: No, I agree definitely with all that and want to definitely add, with the metrics piece, is I feel like a lot of companies and a lot of people and leaders will look at the metrics that are easy to track or, like Ariel said, the ones that we can easily grasp, but they're not the most meaningful. They're not the ones that are really going to help. And then to Rachel's point, then people are going to ignore them. If the health score gives us really nothing to do, if there's really no validity behind it, then why do we even have it? If we really are using it as a tool, or in some cases it is the tool, the holistic score that's supposed to tell us everything, and when you dig into it and you look at it, it really tells us nothing.

So I think that's the piece there, is why I think a lot of people think the health score is kind of crap now, is it doesn't really do anything. It doesn't tell us anything, or maybe we have a couple pieces in there that are helpful, but overall we're not looking at the right things to really move the needle and get ahead of any of the risk or churn.

Kristi Faltorusso: Let me jump ... I want to add something. Sorry, Ariel. So here's something else I want to add to this, and maybe this segues where we go next with this, but I think the objective is all wrong on what the health score is, also. If you ask five different leaders, you're going to get five different answers onto what they think the health score is supposed to be doing. I've got people who say, "Well, it's going to tell us who's renewing or who's churning or what stage they're in or what milestones they've hit or how they're using the product." And I think all of those could be valid, but the fact that any one organization is going to have multiple views on that, that's a problem. There's a big disconnect there. And also, if those are the different use cases, there should be different data feeding into them.

So that said, I want to understand from our panelists, as you guys think about the design of this, what is the information that you believe is even useful in driving what this could or should be? Because the inputs, I think, matter if we think about it being useful at all. I think a lot of companies get hung up on historical data points and it's a snapshot view. We lack trends, we lack anything that is predictive or future state. And I feel like that makes it stagnant. Also, not useful. So just curious, as you guys think about the inputs of what could possibly be useful, since I think we all agree that it's trash, if you were designing it, what would you put in it? How would you think about the inputs?

Ariel Benzakein: Can I just address-

Andrew Marks: Historical data. That's a really good point. Historical data trends. I think we spend too much time focused on what's happened and not enough on what's happening.

Kristi Faltorusso: Andrew, why is the windshield bigger than the rearview mirror? We should be looking forward, not back.

Andrew Marks: Yeah, exactly.

Ariel Benzakein: So one of the problems there is that people build health scores to measure activity rather than intent. So if they-

Andrew Marks: Outcomes.

Ariel Benzakein: Right, exactly. Can I just back up one second because I want to add on to something that Krista ... Or what Krista was talking about, and then I'll stop. One of the main problems beyond what you brought up a minute ago, Krista, is that people don't validate the health scores. I actually just did two projects in the last six weeks where companies hired me to build their health score. And the first question I ask is, "Did you backtest this against your last 20 churn customers?" Both times the answer was no, and that's super surprising. So people will grab a template from a blog post or an expert or whatever, and it just doesn't work. So just wanted to throw that out there too.

Andrew Marks: And the problem with that, a problem with half-assing it like that, is that you start throwing out these scores. You say, "Hey, this is accurate," and it's not and it's bullshit, and then people lose faith in the score. I spent nearly a decade in analytics and BI. You have to be really careful about what you put out there because if you put out bullshit and people call, "Bullshit," on you, then the next time you put something out and you say, "No, no, this is right," they're like, "Yeah, I don't think so. I'm going to be skeptical."

Ariel Benzakein: Yeah. Well, for example, here's a good one showing intent rather than activity. Executive sponsor changed. Now, building that into your CSP isn't easy, but that's a huge red flag. So that should affect a health score. That's just one example.

Andrew Marks: Yeah. When a customer champion leaves, there's a 51% chance the account churns within the next 12 months. And that number rises to 65% when the champion lost is a senior executive. And that's a study done by Sturdy and ChurnZero from their big rig conference last year.

Krista Roberts: Yeah. I think looking at the metrics that we should use, the data that we should use that actually matter, I think one of the biggest metrics and areas of data that most obviously SaaS companies are looking at are usage, but we really need to be focusing on the trends, not the volume, because I think the big thing is ... Okay, how many logins, how many page views? Again, this was in the past. This is what have we seen. It needs to be more of the deltas. What is it in the 30, 60, 90-day usage deltas, feature adoption, momentum? If there's different pieces, different modules, how quickly are they adopting those and using those? And then just even looking at different roles, if that makes sense for your platform, which it does for a lot of us, is admins versus end users versus leaders, what are they using versus not?

And so I feel like so much of us, and I'm guilty of it too ... And some of it is because of the data and what we have available is, yeah, logins and page views and minutes in platform are great, but it's vanity activity. It's kind of vague. It doesn't really give us a lot, where we really need to look at the trends to see what is really going to give us those indicators of potential risk.

Andrew Marks: Well, I want to take a step beyond that. I think it's not ... The vanity metrics, like you said, are historical. The story's been written, right? The best health scores that I have seen have been the ones that are focused on ... I mean, they have those vanity metrics, they have those trailing indicators, but they also have some leading indicators. And the leading indicators are the things that we can have an effect on. I don't want to look at a bunch of trailing indicators or vanity metrics. I want to look at what are the things that can have an effect on those trailing indicators.

Rachel Jennings-Keane: Andrew or anyone else on the panel, I'm curious to understand from your perspective, what do you think is a good set of leading indicators? Because I think that that's something that a lot of people get stuck on. For example, at People.ai, we really care about ... Do we have upcoming meetings scheduled? If you don't, that affects your health score because that means you don't have that engagement.

Ariel Benzakein: No, you shouldn't. Actually, I'm sorry to jump in there, but you shouldn't do that because-

Rachel Jennings-Keane: Shouldn't do that? Okay.

Ariel Benzakein: I would not do that because I've seen so many times ... I can tell you. Well, I don't want to name the company. Recently, I was at a company where CSM activity was a primary metric. So it drives bad behavior. It causes CSMs to just have meetings for the sake of having meetings. So the worst thing you can have are the dreaded check-in meetings. CSMs will do that, and then they'll complain that the customers have gone dark. So the reason the customers went dark is because they're not getting value out of the meetings. So what customer meetings should be, what are your goals, what are the current roadblocks, how can we knock them out? And have an agenda. If you don't have that, cancel the meeting. You're better off not having meetings with customers and giving them check-ins or useless stuff.

Rachel Jennings-Keane: Oh, no. I 100% agree with you. I don't want to have a meeting with the customer if there is no agenda, if there is no roadmap that we're working towards.

Andrew Marks: I have an example, Rachel, from one of our early consulting clients many years ago. A big part of driving adoption was getting people to go through ... Which was the outcome that we were focused on. We want to drive adoption. And in order for the value to really be realized for this particular solution, they needed everybody within the organization that we sold it to, to use the product. And I'm not going to get into too many details about who the product was and all that stuff, but that's the setup.

And so we were focused on the outcome of a successful training session. And we had determined that people had a 95% chance of adopting the product, after they went through the training session, if they had consumed this 20-minute video, self-paced video, before they joined the session.

So what we did is we used that as a leading indicator, and we monitored that. And a week out from the training session, we'd look at that number and we'd see what percentage of the organization that we sold this, the number of licenses we sold to, and we said, "How many of these people have actually consumed that content a week out from the training session?" And we used that as a health indicator. And if it was below ... I think it was below 70%, picked up the phone and called the executive sponsor and said, "Hey, listen, this indicator is telling us that there's some risk in people adopting this thing that you signed off on, that you sold to your CFO, and you want to be successful. We've shown that 95% of people that finish that prior to participating in the 90-minute live training session adopt the product."

So there's an example of a leading indicator that we used as part of the customer health that ended up driving the type of outcome, lagging indicator, that we wanted to see, which was high adoption.

Rachel Jennings-Keane: Yeah. No, I like that example. That's a great example. I also think that some of these leading indicators, i.e., upcoming meeting, needs a process wrapped around it. Our leader is like, "Don't have a meeting to check in. That's the last thing you should be doing." It seems like the most obvious thing in this day and age, but also it's always a great reminder as a practitioner.

Andrew Marks: I don't know about you, Kristi. I get them multiple times.

Rachel Jennings-Keane: You still get them?

Andrew Marks: Multiple times a day. I get emails.

Kristi Faltorusso: Yeah. And it actually still uses that exact same language of, like, "Hey, I'm just checking in." So I would disagree. Well, I would agree in the sense we don't want to do that. But Andrew, your point about the exercise that you went through, it reminded me of Slack and when they were early in their journey, they had a number, a magic number of Slacks that an individual would send to say that they were a Slacker. If they hit that number, that was their magic number, they had converted that person into a lifetime user of Slack. And so it's those types of things.

I think what a lot of companies don't get right and they're not spending a lot of time on is actually mapping out what are all the milestones an individual or a company needs to accomplish in order to be on a path to success. It's very rare that I look at any, and I look at hundreds of health scores, that I ever see milestones in there because they're not easy. They're not easy to track, and I feel like this is a big challenge with a lot of the health scores that we see. By design, and almost intentionally designed, is that they're using what they have. It's not easy to get the data that might be the most pertinent, the information that's actually going to inform. So we use what we have, which maybe is a V1, maybe. I would actually be more inclined to say, "Don't have a health score if you can't put the right things in it because then you're going to start to drive bad behaviors in the business," but a lot of companies rely on what they have, and what they have is trash.

Andrew Marks: I like that. And there's an argument ... To lead to my next question, there's an argument that health scores create lazy CSMs who manage dashboards instead of managing relationships.

Kristi Faltorusso: I like that.

Andrew Marks: Is there truth to that?

Ariel Benzakein: Yes.

Rachel Jennings-Keane: Yeah.

Krista Roberts: Yeah. I agree.

Ariel Benzakein: I think the health score is something that should be used by the leader, not by the individual CSM as much. So just two cents there. I mean, yes, it's going to help the CSM identify some things going on in their book of business, but as a leader, I can see the big picture. And when I see the red flags, I can alert the CSM too.

Rachel Jennings-Keane: I agree, but I also disagree, depending on the size of your book.

Kristi Faltorusso: Yeah, I was going to say, I disagree. We want the CSM to act as the leader of their book. Right, Rachel?

Rachel Jennings-Keane: Because, for example, I have 11 accounts or 10 accounts right now, which is the lowest I've ever managed, but they're also very high value. So they're super strategic. So I'm in there all the time, so I know what's happening. I've got all my fingers in the pies. However, I've had 50 or 60 accounts. And how am I supposed to stay on top of that? And I think having a signal like a health score is better than nothing, because it at least sets an alarm bell off to you or can alert you, to be like, "Hey, your health score is dropping." And it's like, "Oh, crap. I need to go and actually do something. Not just check in, but actually bring something that's of value."

I think I saw a comment up here earlier from Stephan, of how do we approach highly mature customers with strong solution adoption but remain unresponsive? I'd say, Stephan, bring them something that's interesting to the person that you are working with. For example, I work with Sales enablement. So like, "Hey, we have this play we do internally called a go-to-market AI hackathon to help your teams become more familiar with AI." And they're like, "That's great. I need something in my enablement calendar." So it's bringing them things like that that helps them do their job better. Don't tell them about what your tool does, but give them something that I think helps them look good in their job.

Andrew Marks: Something valuable.

Rachel Jennings-Keane: Yes, brings them value.

Andrew Marks: Something valuable to them.

Rachel Jennings-Keane: It looks good in their job. It gets their team engaged, and also helps the company at the end of the day. You got to think about what's in it for them. Why should they get on a call with you?

Krista Roberts: I think with the CSM piece and the balancing how important the success score is to the individual CSM managing the book of business and then obviously the leaders as well, I feel like there should be that balance. I think that, to what you said, Rachel, that for CSMs, it's nice to have that score, again, if it's built properly and has the right data to be able to say, "Okay, maybe I do have a really large book of business and I can help sort that to see what do I need to prioritize on outside of my meetings I have scheduled, outside of other things that I know are happening, so I can pick a handful of customers to really dig into."

But if CSMs are doing the job that they should be doing the right way, then they should be able to spot the churn before systems do. So that's the thing. That's that human element of it. The data is not going to do the job for the CSM. And no matter how perfect the data is, there's just that human element piece to it.

And then it really forces the CSM to not necessarily work ... Or I guess only work to what the score says, but to really force more of the structured inputs that could be the CSM sentiment. So the renewal confidence, maybe that relationship risk, expansion likelihood, things like that, because I think just having open-text notes or binary ... Healthy versus unhealthy isn't really that. That's not going to work in a health score, but I think it is that balance because I know as a CSM, it is nice to have those signals. Again, if I need to grab some customers. Maybe I have my blinders on. Maybe, again, everything looks fine. They just renewed or they renewed eight months ago and it's a two-year contract, so I'm not really worried about it, but there could be something out there that I need to be worried about, regardless of what the contract says.

Andrew Marks: The problem is, though, that mediocre health scores that are telling you something but maybe not telling it accurately is more of a problem than not having one. There's a Vitale survey mid-year last year where they talked about CSMs spending nearly two thirds of their time on admin work. You got a mediocre health score and you end up sending the CSM down a rat hole that, actually, there wasn't an issue there, or maybe they should have been looking at something. It causes so much stress and unneeded extra work for a role that already is overburdened with admin.

And by the way, folks, please use the Q&A button to ask questions. We're just using the webinar chat for commentary, but we will get to questions here in about 10 minutes.

Kristi Faltorusso: All right, Andrew, I'm going to pick on some of what I'm reading in the chat a little bit, and only because I've also had this experience at client success, but everyone's always looking for a template. Everyone's always looking for a best practice. And my problem with that is that no two companies are the same, which means no two inputs of what the health score should look like should be the same.

And so I'm actually going to swing the other way and say I don't believe that there's a best practice when it comes to the health score because everyone's business, your maturation, your company segments, all of that, is very unique. Even having a one-size-fits-all health score for all of your customers, that's crazy to me. But then again, so is also segmenting your customers based on ARR, but that's not this topic. So I won't go down that rabbit hole.

But I think that we need to get away from this idea of templates or what worked for you and asking people, because I think you need to look outside in and not inside out. Stop focusing on your business. Start focusing on your customers, think about it through their lens and what they should be doing. What does a great customer look like? How does a great customer behave? What are those behaviors? And then on the reverse, what signals bad behaviors? This tells me my customer is on my naughty list. They're not doing what they should be because they're not going to get the value that they purchase when they purchase our product. I think those are the things that we need to be looking at.

Andrew Marks: There's the buzzword right there, is value, right?

Kristi Faltorusso: Right. We keep saying it.

Andrew Marks: We all should be focused on how do I make sure my customer is getting value? Right?

Kristi Faltorusso: Right. Well, half the CSMs ... Let's be honest. Most CSMs don't even know what their customers' goals are.

Rachel Jennings-Keane: Kristi, I agree with what a lot of you just said. When I first was tasked with building a health score back in 2016, obviously I went scouring internet for all of the templates.

Kristi Faltorusso: I'll give you ... 2016, you were allowed to do that. 2026, we need to know better.

Rachel Jennings-Keane: I still think these two questions are very true, that you should be asking yourself that go in that. Like you said, what does a good customer look like? What does a bad customer look like? And then what are the attributes of those? And it's an exercise I think that's really good to get the teams to do because you start to see themes. And I did this with the team, and it was really interesting because everyone's like, "Oh, well, this is what I think a really good customer is." And it was interesting to see from different CSMs, who had different books and different verticals, what that actually looked like, because then you can start to, I think, identify that. And it varies. You shouldn't just be a blanket health score for all. I don't think that-

Andrew Marks: So Rachel, double-clicking on that, were you describing the activities that the customer was achieving?

Rachel Jennings-Keane: No. The outcome.

Andrew Marks: Or were you talking about the value that they were getting out of your solution?

Rachel Jennings-Keane: Yeah, or the value they weren't getting that they were sold. That was also really important.

Andrew Marks: And Ariel mentioned this at the beginning, right? And we talked about this briefly at the beginning. It's not about tracking the activities.

Rachel Jennings-Keane: No.

Andrew Marks: You need to be tracking the outcomes. That's where the focus needs to be. Sorry, go ahead.

Rachel Jennings-Keane: How have we helped their business in a workflow, i.e., we saved them four hours on payroll a week. Four hours is a big amount or whatever. That's an outcome for them.

Andrew Marks: Yes.

Ariel Benzakein: Yes.

Rachel Jennings-Keane: And that was what we brought to the session. I don't want to hear about ... You did all of these things. What were the outcomes-

Andrew Marks: At the end of the day, it's all about how much money am I helping you make? How much money am I helping you save?

Ariel Benzakein: But it's beyond ROI a little bit. I mean, that's important. Especially when you're doing a QBR, you want to show the ROI. That's super powerful. But if you look at the ChurnRX research, great gains, you know that when customers achieve their results, they stay 6X as long. So one of the things that I put into health scores, and I also measure CSMs individually on this, if you have success plans ... And if you don't, you're not doing Customer Success. I mean, that's one of the most important things to do. You should be tracking the goals that the customer wants to achieve. Next 30 days, next quarter, all year, it doesn't really matter. You find the right cadence for each client.

And then you should track that in your CSP. For example, I was a client success customer in my last job, and we had all the goals for enterprise, strategic, and most of the mid-market clients in the system, and we were tracking are they hitting those goals or not. And part of that was built into the health score. I even built into the health score whether or not they had goals, which is kind of important too.

So it also should be a metric for individual CSMs. You should look at not just NRR and GRR, which are super important on an individual level, but also what percent of their customers' goals are actually being achieved. That's huge. That's really what Customer Success is.

Andrew Marks: At the end of the day, it's all about delivering the value. It's not about activities. It's about outcomes, because when it comes to budget season, they're not going to be interested in, oh, here's all the shit that we got done, all the activities we did. It's how much money are we making? How much money are we saving? How is this helping us achieve our overarching strategic objectives as an organization?

You don't want to be at the top of the list of potential vendors to cut. You want to be at the bottom of that list. And the only way you do that is by positioning yourself as a critical part of their success. And so you have to go beyond the activities and translate that value into ... This is what it means to your organization. Let's see.

Kristi Faltorusso: All right. I got to double-click on something, though. We have to also just live in reality with the scale of some books of business. So Ariel, to your point about the success plans and all that stuff, I think in a high-engagement model, sure, that can be the reality, but that's not the reality for most organizations. And most CSMs have a book far too large to have that level of engagement and that level of intelligence on any account, or even that level of collaboration. So I think it makes sense in certain segments and certain businesses. I would actually challenge to go as far as saying this is something that the Product teams should be listening to, because why aren't we building this stuff into Product? Why aren't we capturing the right moments in the product? It should be intentionally designed into the infrastructure of the product, not the byproduct of the people supporting it to bridge the gaps.

Ariel Benzakein: Yeah. Tech touch CS is-

Andrew Marks: I agree with you and disagree with you, Kristi. I know I'm going out on a limb here by disagreeing with you.

Kristi Faltorusso: You can agree with me, though.

Krista Roberts: Do that first.

Ariel Benzakein: I agree with you too. I mean, tech touch CS is a totally different animal from strategic enterprise.

Kristi Faltorusso: No, but Ariel, not even tech touch. Tech touch would assume that maybe you don't even have designated CSMs. If you've got a CSM with 50 accounts, that might not be tech touch, but 50 accounts, to have the level of a high engagement model in a solution that might be somewhat complex, that's a lot. I think that we forget sometimes how much work actually goes in to support any one customer. So I don't know.

Ariel Benzakein: I mean, if you have an enterprise CSM managing 150K plus accounts and they have 50 of them, that's an org design problem. I mean, that should not be happening.

Kristi Faltorusso: And I'm not even talking about that. It could be significantly lower in value, but still 50 accounts. Let's call it even 40,000. And I don't even care how much money they spend because the spend, to me, is irrelevant. If all of our customers should be getting value, should a customer who's spending $10,000 not get value and a customer that's spending $100,000 get value? No. All of our customers should get it. How we deliver that, though, should be the main focal point.

Ariel Benzakein: Yeah, but Kristi, if you're spending a lot of time on those $10,000 customers, that's not correct. I mean, you need a lot of those to churn to equal to the $100,000 customer.

Kristi Faltorusso: Sure, but everybody's business is different at different stages. And that's what I'm saying. I'm just saying that there's no one way to do it, and so we just shouldn't put a blanket over it to say that everyone who's managing accounts should be doing success plans or should be doing these things. It should be intentionally designed by the business to achieve the outcome for the organization. So I just don't want to generalize things.

Ariel Benzakein: Sure. I mean, obviously, different segments have different health scoring too. I mean, your enterprise health scoring methodology is not the same as your SMB or your mid-market. So yes, but focusing too much attention on the small clients is not ... It's not worth it. I mean, they're not going to get that level of service.

Andrew Marks: I think these days, you can use a combination of technology to ... So first of all, Kristi, I do agree with you that Product should be on this freaking call. As a matter of fact, Product, we look at ... And you're going to be hearing a lot of this out of us this year and moving forward. The revenue organization, and disagree with me if you think this is different, should be considered Marketing, Sales, Customer Success, and Product, because they are all responsible for revenue. And they all need to be thinking about their roles from a Customer Success lens.

So I 100% agree with you, that Product should be building this sort of shit into the product, but I also think that there are ways in which you can leverage technology and be very prescriptive about things like success plans and capturing outcomes and things like that, and then have a more ... We call it reactive proactivity approach to alerting CSMs, "Hey, you need to pick up the phone and call," whether it's a pooled model or it's a one to ... I got 300 accounts. At least there's something there that says, "Hey, there's something that might be wrong here. You should probably look into it."

Kristi Faltorusso: And listen, I love the idea of technology. I also live in reality, where there's a lot of companies that don't have budgets, don't have that tech stack. So I want to diversify the talking points on the call so we cover everybody. We don't just speak to people that have access to these tools and resources.

Andrew Marks: Don't get me started with budgets, man.

Kristi Faltorusso: Budgets. I know. I don't want to send you.

Andrew Marks: When it comes to sustaining revenue.

Kristi Faltorusso: If anyone wants to go and get-

Andrew Marks: You saw my LinkedIn-

Kristi Faltorusso: I was going to say your LinkedIn post took a turn.

Andrew Marks: That LinkedIn post was ... I got 170,000 impressions on that. So it definitely struck a nerve.

Kristi Faltorusso: Because there was a lot of emotion behind your post.

Andrew Marks: You what?

Kristi Faltorusso: I said there was a lot of emotion behind that post.

Andrew Marks: Yeah. Yes, there was. All right. Let's get to some questions. I asked my panelists to take a look at the Q&A. I'd like to answer some questions from the audience. Remember, we're going to answer them based on most upvotes. If you see a question in here that you want to jump in on first, hit that answer live button. I see Ariel's already done a couple of them. Otherwise, I'm just going to ask the entire group. So if you see something there, hit that answer live button and we'll get started here with David. David, thanks for joining us. David asks, "If we're wanting to include some amount of weight on a subjective CSM feedback component to health scores, how do you turn that into something quantifiable beyond red, yellow, green?" Include some amount of weight on a subjective CSM feedback-

Kristi Faltorusso: I mean, are we looking to generate a number, as opposed to red, yellow, green?

Andrew Marks: It's like a gut feel.

Kristi Faltorusso: And then have ranges?

Krista Roberts: Like a range. That's what I was thinking.

Kristi Faltorusso: Yeah. So is it like green is 100 to 80? Again, I'm simplifying this. Is that the idea here, that you need a number so we can quantify it and then suggest that ranges mean something internally?

Andrew Marks: Yeah. I think that's what ... David, if you're on and you want to clarify that, just drop it into the chat.

Krista Roberts: Yeah, that's what I was going to make you do.

Andrew Marks: You want to include some amount of weight on a subject ... Is he still here? David, David. David. Yeah, David, you're still here. Yeah, CSM sentiment, as Josh mentions. We're wanting to include some amount of weight on a subjective CSM feedback component to health scores. How do you turn that into something quantifiable beyond red, yellow, green?

Ariel Benzakein: So CSM sentiment should be part of a health score, but it should be weighted low because CSMs will tend to look for who's happy and who's not.

Yeah. So that's not a good predictor of churn, but it's important to put into health score, but I wouldn't put it more than 15% max in the weighting of your health score.

Kristi Faltorusso: Why don't just have it as a separate number? I think the metric itself is very telling. I wouldn't put it in my health score. If we said a health score was a behavioral activity monitor, how are our customers behaving? Are they behaving like good customers or bad customers? Take the sentiment out of it. Make that its own metric.

I do think that there is value in there. And I think if CSMs don't know how to assign sentiment properly, they should be coached on that. Maybe call Andrew. I'm sure he's got a course or something he could do to help you.

But alternatively, M&A for me is a big one. You learned things about customers in conversations in that partnership that might not show up in a health score. I could have a customer who is behaving like a good customer, all signs point to yes, but I get on a call with them and they were recently acquired. That might change the trajectory of the partnership over time, or at least the motions in which we run at that. So I'm just saying I don't want to bury a metric that could actually be valuable. I would just break it out.

Andrew Marks: I like that. I like that you break it out from the health score. I agree with you. I don't think it should be necessarily ... If it is included in a health score, to Ariel's point, it should be a very small weight. But I also like the sentiment as a lookback and say, "Hey, you know what? That customer churned, but you had ..." As a green sentiment, where's the disconnect? Is there questions we're not asking? Was there information they weren't sharing with you?

Kristi Faltorusso: It's good for coaching.

Andrew Marks: Right, exactly. For coaching, exactly. Is the fact that you only had a great relationship with the key stakeholder and none of the other stakeholders, maybe that played a role in not raising that red flag that there was something wrong.

Rachel Jennings-Keane: I think it also ... There needs to be a good definition of sentiment and how do you ... As a CSM, I'm judging sentiment, like you said. Oh, I have a great relationship with the person I talk to all the time. So I think the company and the organization needs to define what does good sentiment mean as a CSM, because I'd be like, "Yeah, I have great sentiment with this account." As you said, I actually had that happen where I got on a call where they have all the green indicators, but they're being acquired. Thank god they're being acquired by another customer. So I'm going to take a churn, but we're going to obviously have them migrate over to that other customer account in that regard. I was very fortunate in that situation.

Andrew Marks: And you know what? You will always have watermelon accounts.

Rachel Jennings-Keane: I was about to say that, actually.

Andrew Marks: Watermelon accounts, right?

Rachel Jennings-Keane: Yeah.

Kristi Faltorusso: Green on the outside.

Andrew Marks: Green on the outside, red on the-

Rachel Jennings-Keane: Green on the outside, red in the middle.

Kristi Faltorusso: Red on the inside.

Andrew Marks: And you cannot solve for that. They will always be there, whether it's an M&A or there's a decision being made at the board level or e-staff that you are not privy to, you're going to get surprised.

Rachel Jennings-Keane: Yeah, I agree with you on that. I think Bob London, he has a great course on questions, and there's one question I always come back to, of, "Hey, I want to check in and hear from you how you think this partnership is going from customers, because I'm getting a sense of these things from you and I just want to check, am I reading this correctly?" And it's a very scary conversation to have because sometimes it's like, "Yeah, we're going to churn." But I find that out eight months before the contract ends. So it's like ... Okay, there's enough time to have a discussion about this. And it actually-

Andrew Marks: Yeah. You need to be asking those questions with enough runway so that if there is a chance to save the customer, you can save the customer.

Rachel Jennings-Keane: If I'm taking over an account, for example, I'll ask that question upfront. How is this partnership going for you, from your perspective and the value you are getting? Rather than me getting all of the other analysis that we get internally from our lens, like what Kristi says, outside in. And then I get a better idea of how much the house is on fire, from the customer's perspective.

Andrew Marks: Right. Exactly. Okay. Awesome. David, thanks for the question. That led to some good conversation here. And just a reminder, folks, we go until a quarter past the hour. So if you can stick around, we will keep going until 12: 15 Pacific, and try and answer as many questions as we can.

All right. Our next question comes from Derek. Derek asks, "What data inputs matter the most for predictive trends for a useful customer health score, mainly for a SaaS company? What leading indicators are the ones that research has proven to be the most valuable?" It depends.

Krista Roberts: Yeah. I think that goes back to the ... Each business is going to be different. I mean, it's hard to say ... Just again, to put a blanket, these types of predictive trends or indicators are going to show that this customer is healthy and successful versus not. It's really going to depend by the company and the product.

Andrew Marks: Think about that example I gave earlier. We found this thing that was predictive of success, and it was unique for that particular company in their particular situation. That's the type of thing that you want to be thinking about. How do we ensure that the right people are doing the right things in the right ways and at the right times to have the effect that we're looking for them to have?

Rachel Jennings-Keane: A way I've looked at this before is you obviously have a lot of data. Telemetry data is a great place to start, I think. And looking at what are the most sticky parts of your product and where you see the customers who stay the longest, do they use those sticky parts of the product or not? It's coming back to what do good customers look like and backing into some data. So I would use your data team to explore that first because you probably have a hypothesis, right? Does these data inputs also ... Do our most tenured customers use them the most? I think that's a good place to start with that, and then you can start to back into some of more of these leading indicators from there. But I think it's good to understand what has happened, to help you move towards a predictive trend because if you don't know what's happened and what's happening, how can you get to predictive?

Ariel Benzakein: Yes, that's absolutely true. And I think most companies do it backwards. They start with data, then they try to build a health score. The right way to do it, in my opinion, is go back and look at 10 to 20 customers that recently churned and understand why they churned. And then build that, whatever that is, into your health score. I'll drop a resource in the chat that you can use to analyze your customer churn reasons.

Andrew Marks: I love the strategy, though, for identifying the features that you know that they're getting high value from, but what you need to do is I think you need to take it a step further and say, "Okay, well, what does that translate to?"

Rachel Jennings-Keane: Yeah, what's the value or the outcome? Yeah.

Andrew Marks: Revenue, expense, risk mitigation, whatever it is. You know that, hey, when they use this feature, they are reducing what used to cost them two hours of work to 15 minutes. I can develop an ROI model based on that. And I can also use that ... Not only is that a great indicator that, hey, they're getting value, but I can actually turn that into a transportable message. Anybody else? Anything to add to this? All right. Derek, thanks for the question.

Let's see. Refresh here. Our next question comes from Sarah. Sarah asks, "In the absence of robust engagement and usage data, and at current state, a very low-touch CX, how do you recommend building a rubric for a health score?" And it looks like, Ariel, you want to jump in on this out of the gate.

Ariel Benzakein: I did? Let me see. I don't remember. I'm sorry, can you repeat what it was again, Andrew? What was the question?

Andrew Marks: In the absence of robust engagement and usage data, and at current state, a very low-touch CX, how do you recommend building a rubric for a health score?

Ariel Benzakein: Yeah. So usage data I think is only so valuable. So what a lot of companies will do, they'll do something like number of logins. That's showing activity, not intent, like I was talking about before. So that's not valuable at all. I think what you want to do with usage data is look at the differential. So what is it over the last 30 days? How did it change, versus the 30 days before that? I think that's what you want to do with usage data. I don't know if everybody else agrees, but I've found that to be more effective than things like logins.

Krista Roberts: Yeah, I agree. I think that's one of the biggest pieces of advice that I always give when I'm working with customers and building their health score, is what are ... Yeah, login's fine, but again, that doesn't mean anything. I can log in and just have the app open on my computer all day, but I'm doing nothing. What am I actually doing? And then that's pairing it with the features that we feel, as a company and our Product team, that are the sticky features or the ones that are going to equal success and equal positive outcomes and what the customer wants to see. So if a customer's goal is to do X, Y, Z, and they're not using the three features, they're not logging in and actively using those features, then they're not going to meet that goal. They're not going to see that value. So it definitely goes beyond the ... Are we just logging in and the activity of that? Are we actually adapting into what level of ... That is success for those specific features.

Ariel Benzakein: Krista, I have a question for you. Many places I've been, we've had on-prem products. So what do you do, in your opinion? And I think I asked you this question in the past when you were my CSM, but what do you do in those cases when you can't see usage then? I mean, I guess you just do everything else, but it's tough. Somebody asked that question in the chat too, but I'd be really interested to get your take on that.

Krista Roberts: That's a great question because, actually, years ago, one of the companies that I was at and built and led the CS team, I would say 70 to 80% of our customers were on prem. So we did not have access, for the most part, to how they were actually utilizing the products.

And so what we did there and what I advise, and it kind of goes into one of the questions I had marked to answer, was a client scorecard. Again, this is, I guess, that ideal. If we do have regular engagements and we are actively working with our customers, but you could find ways to do it at scale, asking them how they're using the product, because they know that it's on prem. They know that we can't see the activity. We can't see how they're using it. And so it's just having those conversations and saying, "This is having a grid or a scorecard of what we feel are successful customers and the goals that you have for our product are doing and using. How are you doing in these areas?" And being able to actually have the customer tell you.

And I know that it can seem kind of silly, but that's what we had to do where ... It was kind of wild because I'm like, "I don't know how many ..." It was a security safety software, and I'm like, "I don't know how many reports your team's writing, or how many ... Whatever. What you're resolving because I can't see any of it. So you have to tell me." And that can be tricky. So I think that can be somewhat of a solution there.

But yeah. Then, of course, it becomes the bigger scale piece of ... We have 200 customers that are on prem and one CSM overseeing those. How do we do that? There's some things we could do at scale. Surveys, forms to send out, things like that. But yeah, that part can be tricky. That's where we can go back to ... It might not make sense to have a health score for them. Let's have different metrics that we're looking at because, again, I'd rather not have a health score that's not going to give me anything.

Andrew Marks: I actually solved that problem for a customer of ours. Early customer. Actually, this technically was my customer before I spun up the business. On-prem company that ... You ever call a support number and they tell you that you're X number in line but we can call you back. We can save your ... So this is the technology. Virtual Hold Technology was the company. They've been acquired and PE and merged and whatever, so they're not around anymore.

But what we did, same challenge. 98%, 99% were on prem. So we're talking really early SaaS days. We created a health check script that we would ask the system admin to run on a quarterly basis. And this health check script, I mean, it was a health check, but it gathered up a bunch of data, and we were very transparent about the data that we were gathering. And we'd say, "Run this script and it's going to kick out a file and here's what the file has in it. And when it's done, kick it out, send it to us. And we're going to analyze it to make sure that you are operating our software on your premise at the most optimal settings."

Ariel Benzakein: So we did that-

Andrew Marks: And from that, we were able to determine how healthy ... Hey, are they using the features that they should be using? Are they getting the type of performance that they're expecting? And this is the type of software where it was all about helping them provide their customers with a better experience.

Ariel Benzakein: The problem though ... And we did, actually, what Krista was talking about and what you're talking about. The problem then is getting it back into the CSP if you've got tele-scores, because most of them don't make it that easy to do that, unfortunately.

Andrew Marks: Well, we did an analysis outside of the CSP and we had a couple of different indicators, and then we fed that into the CSP. And it wasn't a CSP. It was a CRM. I think there were four or five indicators that turned red, yellow, green. Hey, for this thing, they're green, but for this thing, they're red.

Krista Roberts: Yeah. That's where you could have that range for each of those, and then that could be what is in the health score maybe, in those fields. But yeah.

Andrew Marks: Awesome. Sarah, thank you for the question. Ariel, if you can hit done on that. Our next question comes from Narupa. I hope I'm pronouncing that right, Narupa. In my experience, high usage does not always prevent churn. It can actually accelerate it as needs become more sophisticated. With the current AI hype, many power users are now looking for automation to replace manual tasks they've mastered. How should CSMs shift their strategy when a client is maxing out current features but is starting to look elsewhere for AI-driven efficiencies to find that strategic ROI? Ariel, you want to jump in on this first as well?

Ariel Benzakein: Yeah. Again, I would just caution about usage in general. It is such a thing that's measuring activity versus measuring intent. So I wouldn't even weigh it that high in the score. When you talk about AI-driven efficiencies, are you talking about ... I just wanted to get a clarification from the person that asked the question. Are you talking about internally with the CSM or are you talking about the customer doing that?

Andrew Marks: Yeah, Narupa is not online anymore. So I would say give it your best shot.

Ariel Benzakein: Yeah. Oh, it does say when a client is maxing out. So I'm assuming they mean the client is looking for those efficiencies. I mean, that sounds to me like she's saying another product has that but your product doesn't. I mean, that's more of a product question or a question for your Product Management team than a CSM.

Rachel Jennings-Keane: I would agree with you on that. How I would attack this issue is I would go to my team and document ... I did this once, because you need to take this back to the Product team and be like, "Hey, this isn't just a $500,000 problem. This is a $20 million problem across our entire book of business." And that gets people listening in other teams because they're like, "Oh, crap. What are we doing to solve that?" What are we going to do to solve that? Because now you have $20 million at risk because we have this gap between what our product does and where our customers need it to be. And I've learned over time that money at risk makes people actually internally pay attention to the problem that you deal with every day.

Andrew Marks: Not just internally. It's your customers too.

Rachel Jennings-Keane: Yeah.

Andrew Marks: It's money.

Rachel Jennings-Keane: If you don't have AI embedded into your product today and you're trying to get buy-in internally to move in that direction, that's a really effective way to show to your leadership, "Hey, I've gone and documented this is the problem, and this is how much the problem is worth to our business."

Ariel Benzakein: Yeah, that's such a great point and that's what you should do. I think there's another thing in this question that's implied, which is usage will go down as AI usage goes up because there's more efficiencies, so the product usage is going to go down. But if you're measuring that usage, you'll see it go down, it's going to affect the health score, but then it's going to even out again. So I wouldn't worry about it long-term, but it's going to make an inaccuracy in the short-term, for sure. That's an interesting point.

Andrew Marks: Yeah. At the end of the day, show me the money. Show me the money. That gets people's attention. All right. Next question comes from Rebecca. Rebecca. Rebecca. Good to see you, Rebecca. Glad you're here. I appreciate Krista's point that CSMs should know their customers, but I have found data to be important for high-volume CSMs with hundreds of customers. I'm wondering if any panelists want to speak to volume number of accounts per CSM as a factor when a health score should be utilized.

Krista Roberts: I can speak to that. I think we touched on it a little bit, that this is where having different health scores for different segments of customers can be helpful, versus having just one blanket health score for your full customer base. So if you have 200 customers and 50 of them are in this lower tier of ... In this, I know it was hundreds, so we could use hundreds again, that they maybe have a CSM assigned to them, but that's just for someone to go to if something crazy's blowing up, but they really don't have a true high engagement relationship with them. That is going to be a completely different health score than those strategic accounts where I'm only managing five to 15 accounts and I should really know everything that's going on with my customer because I'm working with them every single day, probably.

So I think that's the first thing, is having different health scores. And again, depending on the data that's available, depending on your product, that health score could be just those usage metrics, again, that are the valuable ones. Not just the logins, but how they're actually utilizing those key feature functionality. Any way that we can try to track that because that's where, again, we have that huge segment of customers that ... Do we even know if they're utilizing the product or not?

And I do feel like that's where partnering with Product, figuring out what are some things that we could pull and track could be valuable, and having just a completely different health score or some way that we're looking at it because we're not going to be able to have CSM sentiment, we're not going to be able to have some of those things in there because we just don't have that relationship.

You could have Support ticketing for some of those, even some of those customers or some of my customers, those are the support customers that their CSM is support. So there could be some metrics you could pull from your Support ticketing app to show, again, not number of tickets, but some indicators of ... That could raise the flag of tickets that are reopened, tickets that have been open for X number of days, that kind of thing, because again, number of tickets isn't always an indicator of risk. A high number of tickets is they have a lot of users and they're all using the tool, so they have a lot of questions. That's fine. I'd rather have a lot of tickets than no tickets at all from the customer because they're probably not using your tool if they have no Support tickets. But I think that could be valuable for all customers, but for that segment of customers, to see how are they interacting with our support team and ticketing and those tools there.

Ariel Benzakein: Ticketing is a sign of health, unless it's a lot of high-priority emergency.

Andrew Marks: It can be a red herring though. I've worked with customers before where low ticket volume is bad and low ticket volume is good.

Krista Roberts: Right. Type of tickets. I think type of tickets. And I think that's where, depending on the ticketing system that you're using ... So here at ClientSuccess, we are just transitioning all of our support into Intercom, and you can classify different types of tickets. And even utilizing, I think for us, the percentage of tickets that can be resolved using the knowledge base and the AI features in there before needing to even open a ticket, that could be the metrics that you're looking at, but having different types of tickets where it's truly a break fix. Something's not working, and how that's identified versus not.

And there's your product too. I mean, if your product's just really simple and there's not a lot to it, you might not have tickets from some customers. And again, that might not be the worst thing. I use apps every day in my life that I've never had to open a Support ticket and I love it and I'll continue to renew, but I have others that I don't really use it as much, and then when I go in, it's broken. So I'm probably going to cancel it.

Andrew Marks: Anybody else want to add to that? Okay. I think we got time for one more question. Josh. Let me refresh this. Josh asks, "What are some strategies to tease out customer goals when they're struggling to define and communicate them, especially when they're vague and not easily quantifiable?"

Ariel Benzakein: Yeah, this is such a great question because it's so common. And one of the other challenges you'll find is that the doer that you're talking to on a daily basis, their goals are probably different from the buyer a lot of times.

Andrew Marks: They are. I guarantee it. Guarantee it, they are.

Ariel Benzakein: Guarantee it, yeah. So you've got to take both into account, but to address the immediate concern of they don't know what should they do, you should write the success plan first and then go to them and have a discussion. That works much better than trying to sit down with your day-to-day contact, because they're not going to know, or they might know but they're not thinking of it that way and you're kind of putting them on the spot. It's a lot of work. So do as much of it in advance as you can, but also try to get up the chain and make sure you're capturing everything.

And I think another mistake people make when they're doing success plans, they start too tactical. And I think the SuccessHACKER success plan template is actually a really good one to use for doing this correctly, but start with the high-level business goals, not even something that has anything to do with your product. Just company X, what is your goal for the year? I mean, what are you trying to achieve? And then take it down levels until you get to those tactical things, rather than try to do it the other way around. But right at first, sit down with your contact, validate, change as necessary.

Rachel Jennings-Keane: I have another approach to this, and it's something I learned in my time at Domo. They have this concept which took me ages to grasp, but it's called a 4D value statement. And it's really, I think, a good way of breaking it down when people don't know how to articulate what their outcome is, and taking them on the journey. So typically, they know what the business overarching objectives are. Let's say grow revenue by 50% by 2030 is a nice, easy one that most companies would have a revenue goal of something like that. Okay, great. That's the future state. Then back in, how are you going to measure that year over year? You have five years to get to 2030. So you can take the math of what the business is at today and then work that out.

Current state is ... We aren't even making a current number, for example, but what's the approach? How are we going to get there? And I think that that's where you can start to bring some of what you were saying, Ariel, around some ideas to help tease them out. It's all about doing discovery with them. And it can take them awhile. And if they don't know the answer, I think this is a great indicator that you're talking to the wrong person in the business. If they don't know what the-

Andrew Marks: You're definitely talking to the wrong ... I'm going to call bullshit. I'm not calling you out, Josh, but I'm calling bullshit on this because there is a reason ... Companies don't spend money to spend money. So you need to start at the top. And you need to be looking at what the goals are, starting at the top, and how you can quantify those goals. I mean, you have to start at the top, the key stakeholder. They made a deal with you because they're expecting an ROI. So there is a quantifiable outcome. It's hard and takes some effort to dismantle that and figure out, okay, for each of these stakeholders that I'm going to be dealing with as part of the journey, I need to understand the role and the piece that they play in that overarching business objective that got us the business to begin with. And you need to decompose that. Yes, Kristi.

Kristi Faltorusso: Okay. So I love that you believe that that is what's happening, but plenty of people are securing budget and procuring tools and have no idea how they're measuring success with it.

Andrew Marks: And that's a huge problem.

Kristi Faltorusso: I spoke with leaders. I didn't speak with end users. And I would speak to them about their goals. And very many times, they would be unable to articulate a smart goal. I would get a lot of, "Well, what are other customers doing?"

Andrew Marks: That should be a huge red flag for you right out of the gate.

Kristi Faltorusso: Yeah, Andrew, there is red flags all over the play, all the time. Okay? But I'm just saying that this is not uncommon. So I think that we want to believe that the higher up we go, that there will be clarity, and that's just not always the case. And you know what? I put it back on the CFOs. Who's cutting the checks for these products without goals? I want to blame the CFOs. That's who I'm blaming.

Ariel Benzakein: So that's a Sales problem. Andrew, that's a Sales problem.

Andrew Marks: I'm not buying that though, Kristi. I'm not buying that. And I agree with you, but it doesn't make any sense.

Kristi Faltorusso: They may have a reason. Hold on. Andrew, they may have a reason. They may have a pain, but they don't have a goal. And those two things are not the same. I have a pain, but I don't know how to articulate when this pain is resolved or how I'm measuring that.

Ariel Benzakein: Yeah, but that needs to be determined upfront when you're closing a deal. That's why you need CS involved-

Kristi Faltorusso: Well, this goes back to the Sales governance model that I feel like is not in place in a lot of organizations either, because if they have a pain identified, and again, it's not a smart goal that is being tracked, measured, and monitored without governance around that, I'm sorry. AEs are not going to not close deals because the person that's buying this didn't have the ability to articulate how they're measuring success. If the pain is there, they're going to assume that that's enough. But

Andrew Marks: You can't ignore that.

Kristi Faltorusso: I'm not ignoring that.

Andrew Marks: If that deal gets handed over to you-

Kristi Faltorusso: I agree.

Andrew Marks: In post Sales, you have to be like, "Whoa, wait a minute. They don't even know what their fucking goals are."

Krista Roberts: We do, but they already signed the contract.

Kristi Faltorusso: Listen, as somebody who's on the receiving end of that, Krista and I can attest to this quite a bit, is we're always like, "Hey." Calling fouls left and right.

Andrew Marks: Yeah. So the message here, folks, is don't ignore that.

Kristi Faltorusso: No, listen, I'm not ignoring it. I would fight for it. I continue to advocate for others to fight for it and be part of the solution, but I just don't want to ignore the fact that, regardless right or wrong, it's still people's realities and things that we have to navigate. So I don't want to make assumptions and say, "Yes, the higher up we go, they're going to have these goals." Yes. Should they? Absolutely. Should Sales have done the discovery? Absolutely. Should these things be documented in someplace? Absolutely. Yes, yes, yes. Does that happen? No, no, no. So I just want to be here speaking on behalf of the people that are living more of the reality of what is, not what should be.

Andrew Marks: No, I get that. I agree with you. I understand. It doesn't excuse you though from ... That just means more work for the CS.

Kristi Faltorusso: Yes, yes. It doesn't excuse us from not having it.

Andrew Marks: But it doesn't excuse you from not doing that work.

Kristi Faltorusso: Right. And this is the other thing, is I will never say, "I don't have my customer's goals because Sales didn't collect it." I'm sorry. There's accountability that needs to live on everybody who's facing that customer. And just because some part of the chain was broken doesn't mean the part that you are accountable for should be, or that you should use that as an excuse.

Andrew Marks: All right. All right. Thanks, everybody. We've reached the end of today's session. We're actually over by five minutes.

Kristi Faltorusso: I'm sure you're so happy.

Krista Roberts: Kristi may or may not be on the next one.

Kristi Faltorusso: I may or may be back for February.

Andrew Marks: Of course you will be. I love having Kristi here. We've reached the end of today's session. I want to start by thanking our panelists for sharing their perspectives and experiences. Thank you, panelists. These conversations are only as valuable as the people willing to be honest about what exactly is happening in the work, and we truly appreciate you making the time to be here. Kristi, once again, really appreciate you being here, being part of this. I'm excited about our partnership, and yes.

Kristi Faltorusso: I'll be better. I'll be better.

Andrew Marks: No, I want you to be the same. I want you to be exactly who you are.

Krista Roberts: Be you.

Andrew Marks: This was why I was excited that we're doing this, okay? You be you. To everyone who joined us live, thank you for your questions, your engagement, for being part of this community. If you found today's discussion useful, we'd love for you to continue the conversation on LinkedIn. Tag one of us or SuccessHACKER, share a key takeaway that stuck with you.

Our next CS Mastermind is scheduled for February 18th. I believe we will both be there. I'll be back from Vienna by then. So Kristi and I will be there again, where we'll be diving into how CS organizations can leverage tools such as AI to deliver truly personalized experiences across their book of business. I believe we still are looking for some panelists for that one. So let us know if you're interested in participating or if you know somebody that's got a perspective on that. We hope you'll join us again for what promises to be another thoughtful and practical conversation.

Finally, let me leave you with this, great customer-focused professionals. Whether you're leading a team or you are working directly with customers, don't pretend to have all the answers, but do know where to find them. And that's exactly why we created this series. Have a great rest of your day, a great rest of your week and your month, and we'll see you next time.

Kristi Faltorusso: Bye, everyone.

Customer onboarding is one of the most critical stages in a customer’s journey with your company. Far more than just another item on the “to-do” list, onboarding is when customers get their first glimpse of your product on the way to delivering value. If promises made during Sales aren’t kept, or new customers otherwise feel friction during these crucial early days, they can quickly become a flight risk. One way Customer Success teams can ensure this process is effective–driving revenue and reducing churn–is by mapping the customer onboarding journey.

An onboarding journey map is a blueprint that helps Customer Success Managers clearly see every part of onboarding. By outlining onboarding touchpoints, stages, goals, and milestones, CS teams avoid a free-for-all inconsistent experience and create a structured onboarding process that eliminates gaps in the experience and accelerates time-to-value.

Here’s a step-by-step protocol you can follow to map the customer onboarding journey, tips for making the most of each touchpoint, and common (but serious) mistakes that can derail your efforts.

This article will discuss:

• What is a customer onboarding journey map?

• What are the key stages of the onboarding journey?

• Tips for mapping the journey.

• How to optimize touchpoints in the customer journey.

• Customer journey mapping mistakes to avoid.

What is a Customer Onboarding Journey Map?

A customer onboarding journey map is a structured representation of the path customers take from the moment they sign their contract to when they start using your product independently. It documents each stage, touchpoint, and milestone,  providing a clear blueprint for both your Customer Success Managers and your customers.

Without a journey map, onboarding can become fragmented. Sales promises one thing, Customer Success delivers another, and customers are left confused or unsupported. And when customers don’t know how to use a new product properly, they often churn: studies show that 80% of users have deleted an app because they didn’t know how to use it. A map prevents this by:

• Clarifying responsibilities: Ensuring Sales, Customer Success, and Support know exactly when and how to engage.

• Highlighting customer milestones: From the kickoff call to the first value moment, the map ensures no critical step is overlooked.

• Connecting onboarding to long-term adoption: The journey doesn’t stop once a customer is on their own; it should transition smoothly into value realization and account growth.

• Creating consistency at scale: Whether you have 10 customers or 10,000, a mapped customer onboarding process ensures every client receives a predictable, high-quality experience. 

You can create a broad customer journey map for your typical customer, journeys for different customer segments, and even maps for specific customers, depending on your needs and bandwidth. For example, high-touch enterprise clients might receive their own custom roadmap with a high level of personalization, while an SMB with a more universal use case might fall neatly into a pre-made customer segment map. 

What are the Key Stages of the Onboarding Journey?

Every business has its own unique customer onboarding journey, but overall, the process typically looks similar between organizations. It’s made up of phases that guide your customers from excitement at purchase to confidence in using your product. And when onboarding is done right, it can be powerful for business outcomes: nearly 90% of people say they’re more likely to be loyal to a business that invests in educational and welcoming onboarding content. 

Here are the common stages of successful onboarding programs:

1. Sales-to-CS Handoff

The customer onboarding journey begins when a customer wraps up the sales cycle. At that point, Sales needs to successfully hand off the account, along with any key insights they’ve captured, such as customer goals, expectations, and use cases. This avoids customers having to “start over” and builds trust by showing continuity from Day One.

2. Kickoff

The kickoff (usually a phone call or video chat) sets the tone for the relationship. This stage introduces the CSM to the customers, aligns stakeholders on goals and needs, clarifies roles, and confirms metrics for success. When kickoff is well-executed, it should reinforce the customer’s decision to buy.

3. Account Setup & Configuration

Here, customers prepare their environment for using your product, whether that means technical integrations, data import, user provisioning, or initial configurations. Clear guidance, documentation, and project management are critical for preventing delays or frustrations.

4. Product Training

Now, customers start learning how to use your product. This stage can include live training, role-based workshops, and self-service resources. For example, the CSM might host role-based training sessions for administrators and end-users, while also providing customers with access to an on-demand learning hub. The focus is on building confidence quickly, so that teams can move from learning to doing. 

5. Early Checkpoints & First Value

As training progresses to usage, CSMs should check in with their customers to confirm product adoption and measure progress against goals. The priority here is helping customers achieve their first value moment: a tangible result that proves the product is working for them. Early wins here build momentum and strengthen engagement. 

6. Milestone Reviews

As customers advance, CSMs should measure their progress against agreed-upon milestones. This stage is where CSMs can identify adoption gaps, proactively address risks, and highlight additional ways to drive value. They might see that while the finance team is adopting quickly, the marketing team is lagging, and schedule targeted follow-up training for that group.

7. Transition to Steady-State Success

The final stage of onboarding is the transition into the ongoing customer lifecycle. The customer should now feel confident using your product and see it as part of their day-to-day workflow. 

Master the Execution: Tips for Mapping the Journey

For onboarding journey mapping to lead to benefits like faster time-to-value, improved retention, and expansion readiness, it needs to be more than just a flowchart. 

To make your map effective and actionable, keep these best practices in mind:

1.Start with the Customer’s Goals

A customer journey map should be anchored in what the customer is trying to achieve, not just what steps your Customer Success Managers should take. Use discovery notes from Sales to identify specific success metrics, then design your map around milestones that reflect these outcomes. For example, if Sales captures that the customer’s goal is “reduce manual reporting by 80% within 90 days,” the journey map should highlight milestones like “first automated report created.”

2. Define Ownership at Each Stage

Clarity prevents confusion and stops CSMs and Sales reps from stepping on each other’s toes (or dropping the ball altogether). Document who is responsible at each step, whether it’s CS, Sales, onboarding specialists, or Support. This ensures nothing slips through the cracks, and workflows are smooth.

3. Balance Internal Tasks and Customer Experience

Journey maps often focus on internal workflows, but they should also reflect what the customer sees and feels. For example, instead of “training delivered,” frame the milestone as “customer feels confident in using core features.” This customer-centric perspective helps CSMs ensure customer goals and satisfaction remain top of mind.

4. Build in Checkpoints and Feedback Loops

Your customer may be completing steps, but are they really learning how to use your product and integrating it into their workflows? Create checkpoints where you validate adoption, gather feedback, and see how things are going. If customers aren’t sticking to the journey or they’re struggling, you can recalibrate. This prevents silent disengagement that leads to churn (studies show that more than 91% of unhappy customers don’t tell you they’re dissatisfied, they just leave).

5. Iterate Based on Data 

Treat your map as a living document. Customer goals, product features, and market conditions change over time. Your map should adjust to remain effective. Track metrics like time-to-value, training completion, and usage patterns to identify where customers stall and where they thrive. Refine touchpoints and onboarding content over time to continually shorten the path to value.

How to Optimize Touchpoints in the Customer Journey

Every interaction during onboarding is an opportunity to build confidence, deliver value, and deepen the customer relationship. Understanding and optimizing these touchpoints ensures customers don’t just move through the steps – they make meaningful progress towards achieving their goals with your product.

Here are some tips to keep in mind:

• Align every touchpoint with outcomes: Each interaction should be linked to the customer’s goals. For example, if their main concern is shortening reporting cycles, use the kickoff call to map which product features will directly enable that outcome.

• Use checkpoints to validate adoption: Don’t assume training equals adoption – verify it. For instance, two weeks after launching training, review product data usage. If only 30% of licensed users are active, schedule role-specific follow-up sessions or provide targeted self-service tutorial resources to improve adoption.

• Personalize where it matters: Standardization is critical for effective scaling, but personalization drives engagement, and it’s important to find the right balance between the two. Small bespoke details can make a big difference: while all customers might receive a similar kickoff deck, even just tailoring it with their logo, success metrics, and team structure shows your commitment and helps customers envision success. 

• Leverage proactive risk signals: Touchpoints allow you to catch risks before they escalate into churn drivers, and take corrective action. You can also use digital Customer Success tools to help: if a customer hasn’t logged in within 7 days of setup, trigger an automated alert to the CSM to reach out with a “quick start” call.

• Celebrate progress (visibly): Recognition reinforces value and strengthens relationships (and shows that CSMs are watching and engaged). Idea: when a customer hits their first significant milestone, send a congratulatory email summarizing the impact (e.g., “Your team saved 8 hours this month with automated reporting!”). This reinforces ROI and helps maintain momentum. 
  
  

What are Customer Journey Mapping Mistakes to Avoid?

Your customer journey map can be a powerful tool for driving retention and improving customer satisfaction, but it can also become ineffective if not executed thoughtfully. Here are some of the most common mapping mistakes Customer Success teams should watch out for:

1. Making it Too Complicated

The mistake: Trying to capture every possible step, use case, and customer variation, resulting in an onboarding experience that is ineffective. Three-quarters of customers will switch to other solutions if onboarding is too complicated. 

Why it’s a problem: Maps that include too much detail overwhelm both CSMs and customers, and make them impractical to use.

A better approach: Focus on the critical milestones that every customer should hit, then add breathing room and flexibility for unique needs.

2. Treating it as a One-Off Exercise

The mistake: Building the journey map once and never revisiting it. 

Why it’s a problem: A static map quickly becomes outdated in today’s fast-moving SaaS ecosystem. 

A better approach: Review the journey regularly (such as every quarter). Use metrics and customer feedback to adjust touchpoints and add milestones.

3. Missing the Sales-to-CS Handoff

The mistake: Treating onboarding as a “cold start” instead of building on the Sales relationship.

Why it’s a problem: Customers feel frustrated when they need to repeat themselves, and some of the information might be lost in transit. 

A better approach: Ensure Sales provides documents and data that include customer goals, use cases, and expectations, and review them with the customer during kickoff. 

A well-designed customer journey map sets the foundation for a successful, long-term customer relationship. By breaking the journey into clear stages, optimizing touchpoints, and avoiding key mistakes, Customer Success functions set customers up to achieve value quickly and consistently.

Frequently Asked Questions About Customer Onboarding Journey Mapping

What is a customer onboarding journey map?

A customer onboarding journey map is a visual framework that outlines the key stages, milestones, and touchpoints a new customer goes through from contracting signing to independent use. It helps Customer Success teams create consistency, prevent gaps in the experience, and accelerate adoption.

What are the steps for mapping the customer onboarding journey?

Start by identifying the customer’s goals, and design your map around milestones that reflect those outcomes. Then, define ownership at each stage to avoid gaps and smooth workflows. Build in checkpoints and feedback loops, to ensure customers are succeeding (and to recalibrate if necessary). Lastly, iterate and continuously improve your map based on your findings. 

How do you optimize touchpoints in the onboarding journey?

To optimize touchpoints, align each one with customer outcomes, validate adoption through checkpoints, personalize key moments, and proactively monitor risk signals (like low usage or engagement).

What common onboarding mapping mistakes should I avoid?

The most common onboarding mapping mistakes include making the journey too complex, failing to update the map regularly, and missing the sales-to-CS handoff. 

In Customer Success, high-touch accounts often represent both the greatest opportunity and the greatest risk. These are the customers with complex implementations, executive visibility, and high expectations–the ones who rely on CSM partnerships, not just your product. When managed well, high-touch relationships can become strategic growth engines, driving renewals, advocacy, and meaningful upsell. When mismanaged, they drain resources, stall momentum, and lead to churn. This article explores high-touch clients and how you can not only manage and retain them, but also position them for growth and expansion.

This article will discuss:

• What do we mean by “high-touch” and why does it matter?

• Which customers merit a high-touch approach?

• Strategies for managing high-touch customers

• Leveraging high-touch relationships for growth
  
  

What Do We Mean by “High-Touch” and Why Does It Matter?

What exactly is a high-touch client, and why should Customer Success Managers care? 

High-touch is a Customer Success engagement model where you intentionally invest more human time and specialized resources into a particular account. It emphasizes proactive planning, multi-threaded relationships, tailored enablement, and frequent value checkpoints. 

This is in contrast to a tech-touch or low-touch engagement model that relies on automation and Digital Customer Success to deliver service. 

Characteristics of High-Touch Customer Relationships

High-touch customers don’t just require more meetings. Here’s what this engagement model looks like:

• Frequent, direct interaction: High-touch relationships involve regular communication via direct channels like phone calls, personalized emails, or video chats. These customers expect to be in constant contact with their CSMs.

• Highly personalized service: Each interaction is tailored to the individual customer’s preferences, pain points, and business goals. From customized product offerings to bespoke Success Plans, high-touch relationships require a level of attention to detail that goes beyond what’s typically offered. Research shows that highly personalized customer experiences can lift revenue by up to 15%, lead to better customer outcomes, and accelerate business growth. 

• Increased responsiveness and availability: High-touch customers expect rapid response times – these customers shouldn’t be left waiting.  

• Collaborative and consultative approach: High-touch customer relationships are built on collaboration. Rather than simply fulfilling orders or requests, a CSM's role is that of a trusted advisor, and they should use a consultative approach to guide customers. 

• Continuous feedback and customization: These relationships thrive on ongoing feedback loops. High-touch customers want their input to matter, and they appreciate it when their feedback leads to tangible changes.
  
  

Why High-Touch Matters for Your Business

While high-touch customers may seem resource-intensive for CSMs to manage, their potential to drive growth and long-term success is significant. 

Here’s why:

1. Revenue Potential

High-touch customers are often willing to pay a premium for the personalized experience. This can translate into higher-value contracts, bigger deals, and more consistent revenue streams.

2. Customer Loyalty & Retention

In today’s SaaS ecosystem, customer churn is a constant concern. But high-touch clients are more likely to remain loyal to a brand that understands their needs and consistently delivers on them. Data shows that three-quarters of leaders say most company revenue now comes from existing customers, meaning retention is central to business success. 

3. Competitive Differentiation

In crowded markets, the ability to provide a high-touch experience can set your brand apart. When your competitors rely on a more automated or transactional approach, offering personalized service creates a meaningful distinction. 

4. Expansion Opportunities (Cross-Selling & Upselling)

CSMs deeply understand the evolving needs of their high-touch customers, positioning them for effective expansion execution. That means CSMs can identify strong opportunities to suggest additional services, thus increasing the lifetime value of the customer. 

5. Referral Potential

Satisfied high-touch customers often become brand ambassadors. A well-managed relationship can drive organic growth through word-of-mouth marketing and client referrals. Data shows that 88% of consumers trust friend recommendations over traditional media, and that 64% of marketers say word-of-mouth marketing is the most effective form of marketing. 

Which Customers Merit a High-Touch Approach?

How can CSMs decide which customers deserve a high-touch approach, and which will be just as successful with a low-touch or Digital Customer Success strategy? Given the resources required to deliver this level of service, it’s important to be strategic about who receives it.

Here are the key types of customers who likely merit a high-touch approach:

1. High lifetime value customers: Customers who have a high CLV might not be your biggest buyers today, but they’re the ones who will spend the most during their relationship with your company. They may sign long-term contracts, make repeat purchases, or have the potential to scale with your business. Delivering a high-touch experience helps to protect and grow this revenue stream.

2. Enterprise/strategic accounts: Large organizations, especially those with complex needs or custom implementations, often require a higher level of engagement. These are the accounts that may span multiple departments, involve longer sales cycles, and require deeper integration with your team. High-touch can make a difference here because losing these accounts can significantly impact your revenue.

3. Customers in the onboarding or expansion phases: New customers or those implementing major upgrades or expansions need more attention to ensure success. A high-touch approach during these critical phases can reduce churn, increase adoption, and uncover early upsell or cross-sell opportunities.

4. At-risk customers: In some cases, a high-touch strategy is used not just to grow a relationship, but to save it. Customers showing signs of dissatisfaction or disengagement may benefit from more focused attention, problem-solving, and personalized service to rebuild trust and prevent churn. 

5. Customers in specialized industries: Some industries (such as healthcare, finance, or government) may require additional compliance, security, or customization. These customers often expect (and need) white-glove service, due to the complexity and risk involved in their operations.

The key to determining which customers merit a high-touch approach lies in balancing customer value with business capacity.

Strategies for Managing High-Touch Customers

Effectively managing high-touch customers requires CSMs to create a personalized, proactive, and value-driven experience that builds long-term trust and drives growth. Because these relationships demand more time and attention, having a clear strategy is essential for maintaining quality without causing CSM burnout. 

Strategies to successfully manage high-touch customer relationships include:

1. Start with a Co-Owned Success Plan

Every high-touch relationship should begin with a mutually defined Success Plan – a living document that aligns both sides on what success looks like and how you’ll measure it.

Key elements of an effective Success Plan:

• Business outcomes: 2–4 clear, measurable goals (like cost savings, productivity gains, revenue enablement).

• Value metrics: Agreed KPIs that reflect impact, not just usage.

• Milestones: Time-bound deliverables that track progress toward each outcome.

2. Establish Executive Alignment 

High-touch management requires executive-level buy-in. To build and maintain executive engagement, start by kicking off the relationship with an executive-to-executive conversation focused on business impact. Next, go the extra mile with your quarterly business reviews (QBRs): include a forward-looking segment which breaks down what’s next, not just what’s been done. Another tip? Regularly create one-page ROI summaries that clearly connect your solution to business KPIs your executives care about. 

3. Drive Adoption Through Enablement

High-touch accounts don’t just need attention for attention’s sake: they need structured enablement. You can:

• Create tailored enablement plans with user personas in mind (such as admins, power users, or executives).

• Use live workshops and recorded content for reinforcement. 

• Leverage usage analytics to spot gaps and proactively intervene. For example, if a CSM sees a high-touch account isn’t using a feature they could benefit from, they can start a sequence to educate and guide the customer to promote adoption.
  
  

4. Provide Exclusive Value 

Make high-touch customers feel like VIPs by offering them value that others don’t get – not just in service, but in access, insight, and recognition. You can do this by providing them with early access to new features or products, invitations to beta programs or advisory boards, and custom reports or business insights. 

5. Systematically Identify Expansion Opportunities

High-touch accounts are often well positioned for expansions. But CSMs need to be tactful: upsells or cross-sells should feel like a natural evolution, not a sales pitch. 

Look for revenue signals such as:

• Usage thresholds: Approaching license limits, feature adoption plateaus.

• Organizational changes: New departments, new executives, new initiatives.

• Success milestones: Outcomes achieved, ROI realized.

• Cross-functional curiosity: New teams asking for access or visibility.
  
  

5. Balance Personalization with Process

While high-touch customers require a bespoke approach, you don’t need to reinvent the wheel every time. Customer Success functions that want to provide service at scale combine personal CSM relationships with repeatable playbooks. You can standardize base templates for business review decks, ROI calculators, and adoption plans, for example. Also, use playbooks for standard processes such as customer onboarding, risk recovery, and expansion, but tailor them to each customer. 

One more good practice? Automate things like reminders and health scoring, so your CSMs focus on insights, not admin work. 

Leveraging High-Touch Relationships for Growth

When CSMs successfully manage high-touch customer relationships, they don’t just guarantee expansion: they also set the stage for growth and upsells. But growth in these accounts rarely happens by chance. It happens when CSMs consistently orchestrate value realization. 

Below are the key strategies for high-touch customer growth.

1. Shift the Mindset from Retention to Expansion 

The first step is philosophical. High-touch needs to go beyond “keeping the customer happy” and continuously creating value that justifies new investment. Start by framing Customer Success as a growth engine. Your job is to help customers grow their business and show how your solution scales with that growth. Also, use language that moves the relationship forward: from support to strategy, from renewal to reinvestment. Lastly, adopt the idea that expansion is the natural outcome of progress, not pressure. When CSMs excel at building relationships and fostering trust, they can even execute customer-led growth conversations – where customers themselves recognize that expanding their relationship with your product or service is the logical next step.

2. Integrate CS, Support, and Sales around a Shared Growth Motion

Expansion thrives when sales, Customer Success, and Customer Support operate as one team, because these functions can share vital insights and work towards the same goal.

To make that happen:

• Build clear handoff processes between each function, as well as feedback loops to share key customer insights.

• Create processes for identifying trends and taking action. If Customer Support notices that a high-touch customer encounters the same usage problem repeatedly, they should flag Customer Success to take action.

• Ensure sales messaging is aligned with Customer Success capabilities and bandwidth. The last thing you want is a brand-new, high-touch client to be disappointed because of misaligned expectations during the sales process.
  
  

3. Identify Expansion Triggers and Buying Signals (and Know What to Do Next)

We briefly discussed revenue signals, or the subtle signs that might indicate a customer is ready to expand, such as hitting usage milestones or launching new initiatives. It’s important to clarify what these signals look like, as well as events that trigger expansions. But CSMs should be trained not only to spot these signs, but also to know what actions to take next. For example, if a customer says “We have a new VP of Operations starting next month,” their CSM should have a playbook of what to do, whether that’s email a user-friendly FAQ one-pager, ask to schedule a call with an executive, or run the numbers of what ROI would look like. 

4. Use Business Reviews as Growth Platforms

Executive business reviews (EBRs) or QBRs should not just be for status updates. Structure them to highlight value achieved, and set the stage for what’s next. To make these meetings strategic selling moments, show ROI “before and after” snapshots, ask about next objectives (such as upcoming initiatives or challenges), and present options for future growth as a “what’s next” discussion. 

High-touch customers might involve more legwork for Customer Success Managers. But these accounts aren’t just about doing more: they’re about directing your limited CSM resources towards the few actions that compound value. When Customer Success teams understand the nuances of high-touch accounts, appreciate the value they bring to your business, and know which strategies to use to nurture them, you can ensure your best customers stay with you for the long haul.

Frequently Asked Questions About Managing High-Touch Customers

What are high-touch customers?

High-touch is a Customer Success engagement model where you intentionally invest more human time and specialized resources into a particular account. It emphasizes proactive planning, multi-threaded relationships, tailored enablement, and frequent value checkpoints.

What are the characteristics of high-touch customer relationships?

High-touch customer engagement models require frequent/direct interaction, highly personalized service, increased responsiveness, and using a collaborative or consultative approach.

Why do high-touch customers matter for your business? 

High-touch customers might be resource-intensive, but they also have many upsides, like strong revenue potential, customer loyalty, competitive differentiation, and expansion opportunities. 

What customers merit a high-touch approach?

Customers with high lifetime value, enterprise or strategic accounts, or at-risk customers can benefit from a high-touch approach. Also, consider using this method for customers in the onboarding or expansion phases, or customers in specialized industries. 

What are some strategies for managing high-touch customers?

Strategies to successfully manage high-touch customer relationships include:

• Starting with a co-owned Success Plan

• Establishing executive alignment

• Driving adoption through enablement

• Providing exclusive value

• Systemically identify expansion opportunities

As we step into 2026, the Customer Success landscape is poised for its most transformative year yet. While 2025 introduced us to the possibilities of AI-powered customer engagement and sparked serious conversations about revenue ownership, the year ahead promises to separate the leaders from the laggards. The question is no longer whether CS teams will evolve; it's how quickly they can adapt to a fundamentally different operating environment.

To understand what's coming, we gathered insights from some of the industry's most respected voices: founders, executives, and thought leaders who are shaping the future of Customer Success. Their predictions paint a picture of a profession at an inflection point, where AI integration, revenue accountability, and strategic transformation will define who thrives and who gets left behind.

This article will discuss:

• The 8 major themes shaping Customer Success in 2026

• Why AI becomes non-negotiable (and what happens to teams that hesitate)

• How the CSM role transforms from product expert to strategic advisor

• The rise of CS-owned expansion forecasting

• Finding the critical balance between AI efficiency and human connection

• Taking action on the 2026 landscape

Top 8 Customer Success Predictions for 2026 

1. AI Becomes Non-Negotiable. The Gap Between Early Adopters and Laggards Widens

If 2025 was the year of AI experimentation in Customer Success, 2026 is the year of AI expectation. Our experts are clear: the window for sitting on the sidelines has closed.

Josh Schachter, SVP, Strategy & Market Development at Gainsight, puts it bluntly: "2026 will be the year AI becomes non-negotiable in Customer Success. The teams that sat on the sidelines in 2025 will jump in, and the gap between AI-enabled and traditional CS orgs will widen fast."

But this isn't about adopting AI for AI's sake. Ed Powers of Service Excellence Partners predicts a natural market correction: "The CS industry will coalesce on a limited set of AI capabilities that add value and reject a large set of capabilities that don't." Expect to see teams become more discerning about which AI tools actually move the needle versus those that simply add complexity.

This evolution will spawn entirely new roles within organizations. Guy Galon, Chief of Customer Success at Obrela, sees "a new set of roles created, possibly under Sales and CS operations—experts who can develop and integrate AI agents and tools. They will not focus solely on CS but will also support GTM teams to streamline the use and benefits of AI agents."

Perhaps most intriguingly, Himanshu Garg, Sr. Director of Customer Renewals at Druva Data Solutions, envisions AI moving beyond analysis into active negotiation support: "AI Negotiators will assist in renewal and expansion conversations. AI starts participating behind the scenes during live calls, feeding CSMs real-time insights such as risk adjustments, concession recommendations, negotiation probabilities, and discount boundaries." The result? "Renewal interactions become more analytical, less reactive. Customers begin expecting a data-backed negotiation experience."

2. The CSM Role Transforms: From Product Expert to Strategic Business Advisor

The CSM job description as we know it is being rewritten. Our experts predict a fundamental shift in what it means to be successful in this role (and it's not about knowing your product better).

Chad Horenfeldt, VP, Customer Success at Siena AI captures the transformation: "In 2026, the value of a CSM will hinge on their ability to act more as a business advisor that drives their customer's business forward than a product expert that is focused solely on adoption. Business acumen, problem-solving frameworks, influencing skills, and deep discovery become baseline expectations." He adds a competitive reality: "The companies that invest in training their teams create an unfair advantage over their competition."

David Karp, Chief Customer Officer at DISQO, offers a stark warning: "CSMs who don't become Strategic Advisors (by domain or product impact) will be automated out." But there's opportunity in this shift: he also predicts that "CS leaders will become the 'truth-telling' executives who best understand the most growth opportunities for companies."

Victoria Shapira, Senior Manager of Customer Success at JFrog, sees this evolution reshaping how customers seek help entirely: "AI will replace traditional knowledge centers, redefining how customers get help. Instead of searching through docs or training portals, customers will increasingly turn to AI to ask 'How do I...?' and get instant, personalized answers." The implication is clear: "This will shift the CSM's role away from tactical guidance and 'how-to' questions, toward coaching on why and what to do to drive measurable outcomes—making strategic advisory the true value driver in CS."

Virginia Bloom, Director of CX at Aclaimant, captures the shifting customer expectations of their CSM: "Widespread use of AI will change the nature of customer contact, eliminating the 'low-hanging fruit' and making reactive service less acceptable to customers. Customers are becoming more sophisticated with their own use of AI and will expect their human CSMs to be strategic and data-driven consultants and not just report the news."

Chad Horenfeldt also introduces a complementary role that will emerge: The Forward-Deployed Engineer. “Customers increasingly want hands-on help, not just guidance, and they're willing to pay for it. This role becomes the perfect complement to the strategic CSM, giving customers both strategic direction and tactical execution. It also creates a clear monetizable service layer for CS teams."

3. CS Owns Revenue and Expansion Forecasting Like Never Before

The debate about whether CS should own revenue is over. In 2026, our experts predict CS teams will own expansion forecasting with the same rigor that Sales owns new ARR, and those who resist will pay the price.

Stijn Smet, Head of Customer Success at Whale, makes the case directly: "Customer Success will own expansion forecasting the same way Sales owns new ARR. CS will no longer be 'post-sale support.' It will become a predictable revenue engine responsible for expansion forecasting, pipeline creation, and long-term revenue protection." He adds: "The companies that master this dual engine—Sales for new ARR, CS for expansion ARR—will be the ones that scale to $10M+ fastest."

Maranda Dziekonski, Chief Customer Officer at Fexa, confirms this shift: "In 2026, CS will sit squarely at the center of expansion and retention revenue, with CSMs owning clear targets tied to ARR growth. This shift will formalize CS as a revenue-generating function rather than a post-sales support arm." She notes the implications: "Teams will need to adopt more structured commercial training and data-driven forecasting to excel in these responsibilities."

Dziekonski also predicts a fundamental change in how SaaS companies structure their pricing: "More SaaS vendors will tie pricing and renewals to measurable customer outcomes rather than usage alone. This will require CS teams to act as revenue strategists who prove value continuously."

Julie Fox, Director of Digital Customer Success at Hyland, describes how the CSM role itself is evolving to meet this challenge: "The CSM role evolves into a strategic, revenue-connected function. The role of the CSM is not going away. But the way the work is done will keep changing. Routine tasks, data pulls, and repetitive outreach will continue to be automated, freeing CSMs to focus on strategic alignment, business value, and influencing renewal and expansion outcomes."

De'Edra S. Williams, Chief Customer Officer at Customer Success Revenue Frontier, introduces a new growth paradigm: “In 2026, revenue growth comes from user-led advocacy, peer-to-peer referrals, and user and customer-driven storytelling that power upsells and cross-sells. The modern user-led growth playbook turbocharges NRR."

David Karp frames the stakes clearly: "Revenue responsibility becomes shared leadership, or companies start missing their numbers."

4. Predictive Analytics Reach New Heights: From Health Scores to Value Scores

The era of reactive customer management is ending. In 2026, AI-powered predictive capabilities will transform how CS teams identify and act on risk and opportunity—often before customers themselves recognize the signals.

Amber Monroe, VP of Customer Experience at Paradigm, predicts a fundamental shift in how we measure customer health: "Health scores get retired. AI-generated 'value scores' will calculate a customer's future ROI trajectory and probability of expansion before the customer realizes it."

Chad Horenfeldt sees this transformation making CSMs more proactive than ever: "Renewal risk will be predicted earlier than ever. Advanced AI, product telemetry, and conversational intelligence will surface risk signals long before customers articulate them. CSMs will know when engagement drops, sentiment shifts, or outcomes stall weeks—or months—before renewal danger becomes visible." The implication: "This transforms the role from reactive firefighter to proactive strategist."

De'Edra S. Williams emphasizes how leadership must evolve: "Next-gen CS leaders are integrating AI copilots to forecast churn, accelerate revenue growth, and optimize every customer touchpoint. The 2026 CS leader isn't replaced by AI—they're amplified by it. Leadership now requires fluency in data ethics, prompt engineering, and revenue intelligence."

She also emphasizes the critical importance of data governance: "Modern CS leaders guard their organization's most valuable resource: customer data. In 2026, success hinges on clean, integrated, ethical data ecosystems that enable predictive insights, faster decisions, and precision in every renewal or expansion motion."

Krishna Kant, Senior Manager, Professional Services at IBM, describes how AI and predictive analytics will transform customer experiences: "AI will drive proactive and context-aware customer experiences. It will evolve beyond basic chatbots to systems that understand context, emotion, and intent, enabling businesses to anticipate customer needs before they are expressed—like predicting churn risks, forecasting buying behavior, and personalizing interactions in real time."

Stijn Smet identifies what may become the most important leading predictor of success: "Onboarding speed will become the #1 leading indicator of Net Revenue Retention. Companies will realize that the first 30–60 days dictate the next 3–5 years of customer value. CS teams that create predictable, milestone-driven onboarding will consistently outperform on expansion and churn control."

5. Scaled CS Becomes the Primary Operating Model, Not a Side Program

For years, digital and scaled CS motions were treated as overflow strategies for smaller accounts. In 2026, that hierarchy flips—and the implications for team structure and customer engagement are profound.

Julie Fox describes the shift: "Scaled CS becomes the primary operating model, not a side program. Companies will stop treating digital and scaled motions as something meant only for smaller accounts or overflow. Instead, they will design customer journeys to scale first, and layer human support where it truly adds value." The payoff: "Teams that do this well will have clearer roles, stronger outcomes, and more predictable retention because the experience will finally feel consistent across the entire customer base."

Amber Monroe sees a radical restructuring of CS teams: "CS teams will start to reorganize into pods where a few humans supervise large numbers of AI agents, enabling scalability while preserving high-touch, strategic relationships."

But Josh Schachter reminds us that human CSMs become more valuable in this environment, not less: "The role of the CSM won't fade; it'll grow in importance. As AI takes on the scalable work of managing long-tail segments, the human conversations led by CSMs will become even more valuable. The quality of those interactions will determine the quality of the insights AI can generate." His advice: "In 2026, the best CS teams will invest heavily in training CSMs to ask smarter questions, listen better, and capture the true voice of the customer—because that's what will fuel every AI-driven decision."

Krishna Kant sees digital CS expanding beyond its traditional boundaries: "Digital Customer Success will be a key to scale CS teams across customer segments and not just for low ACV customers."

Victoria Shapira captures the new paradigm: "The shift from 'high-touch' to 'right-touch' will accelerate powered by AI. The winners in 2026 will be teams who redesign their operating model around intelligent workflows, segment-based engagement, and outcome-driven automation—not just those who deploy tools."

6. CS Operations Rises as the Strategic Orchestration Layer

CS Operations has quietly built the infrastructure of modern Customer Success teams. In 2026, this function steps out of the shadows to become the strategic orchestrator of the entire customer lifecycle.

Kristi Faltorusso, Founder & CEO at Kristi Faltorusso, sees a dramatic elevation of this role: "CS Ops will rise with a focus on AI orchestration. As AI becomes embedded across Customer Success, someone has to design how it all works together. Not just which tools exist, but when signals are triggered, how insights are prioritized, and what action actually follows." She adds, "In 2026, CS Ops is no longer a support function. It is a strategic role that determines how intelligence flows through the business."

Faltorusso also predicts a major shift away from rigid processes: "Flexible over rigid playbooks and workflows. The best CS teams are already shifting from rigid workflows to flexible frameworks that prioritize impact over motion. Playbooks will stop being linear scripts and start acting more like decision trees. Guidance, not guardrails." She notes: "In 2026, the most effective CS teams will give their CSMs room to think, adapt, and respond in the moment. Process will still matter, but it will exist to support judgment, not replace it."

The tech stack itself is due for a reckoning. Faltorusso predicts: "Consolidation of tools and platforms. Customer Success stacks have gotten out of control. Customers are done with that. In 2026, we will see a strong push toward consolidation. Fewer tools, better integrated, with AI doing the heavy lifting behind the scenes."

Rod Cherkas, CEO and Founder of HelloCCO, emphasizes what this means for leaders: "2026 marks the shift from AI awareness to practical AI-fluency for post-sale executives. Leaders will be expected to show how they use AI to simplify complex work, improve operational consistency, and drive measurable retention and expansion gains. Investing in your own AI-fluency now will be essential for maintaining credibility and leading successful post-sale organizations in the year ahead."

Angeline Gavino, Founder & CEO of CS RevSpeak, sees AI becoming seamlessly embedded: "AI will show up less as a separate initiative and more as a natural part of how CS teams work. The teams that win will be the ones that design AI to remove friction from the workflow so humans can spend more time on high-value conversations and decisions."

Julie Fox describes how personalization will evolve: "Personalization becomes contextual, not just automated. The shift will be toward systems that respond to customer signals, timing, behavior, and intent. This level of contextual intelligence will help teams send fewer messages, but with far greater impact because they are based on what the customer needs in that moment, not what is sitting in a generic sequence."

7. The Human-AI Balance: Finding Equilibrium in an Automated World

Perhaps the most nuanced prediction theme involves finding the right balance between AI capabilities and human connection. Our experts see 2026 as the year organizations must deliberately architect this equilibrium or face consequences.

Virginia Bloom offers a reality check on AI expectations: "In 2026, the high-flying expectations for AI replacing human roles in Customer Success will hit a reality checkpoint, as companies grapple with the unforeseen complexities of data cleaning, system integration, and training reliable AI agents." But she sees opportunity in this adjustment: "This struggle will validate that AI is not a magic solution and that the strategic guidance and empathy provided by skilled CS professionals remain essential drivers of retention and expansion. Organizations will pivot their AI strategy from replacement to augmentation, leveraging AI as a force multiplier to automate low-value tasks and eliminate blind spots."

Bloom also predicts a rise in emphasis on emotional intelligence: "CX and CS leaders will push Emotional Intelligence (EQ) to be recognized as a leadership competency. Recognizing the direct link between employee experience and customer outcomes, these leaders will prioritize modeling and teaching high-EQ skills like empathy and relationship management."

Stijn Smet envisions the emergence of AI-powered proactive success: "AI will become the 'Silent CSM' driving scaled proactive success. AI will power the majority of early interventions, friction detection, and activation nudges, long before a human ever steps in. Teams that build AI-powered digital success motions will reduce silent churn dramatically and surface expansion opportunities at scale." But he reminds us: "Human CSMs won't disappear; instead, they'll become far more strategic, focusing on relationships, expansion, and deep business impact."

Ed Powers offers contrarian predictions worth considering: "The AI bubble will pop, leading to significant contraction in the software industry. CS teams will be impacted by 'across-the-board' layoffs." He also predicts: "AI hype will significantly drop, and fewer, purpose-built features will include AI capabilities as a footnote."

Guy Galon sees new governance structures emerging: "Customer Success will seek the right balance between leveraging AI capabilities (and the potential errors they introduce) and a human-first approach. This will lead to new use of CSM governance over tools and technology. For example, applying 'error margins' to sensitive and critical decision-making processes to allow humans to review and approve."

Amber Monroe emphasizes the governance imperative: "As generative and agentic AI proliferates in customer-facing roles, CS orgs will start to invest heavily in AI governance, ethical frameworks, and trust-building to ensure transparency, accuracy, and compliance."

Himanshu Garg positions CS as the critical stabilizing force: "CS becomes the central 'Stability Layer' between Product, Sales, and AI. AIs automation accelerates other functions, CS becomes the human integrator, preventing customer confusion. Rapid product updates + AI-driven touches + aggressive monetization → customers need a stabilizing guide to maintain trust and continuity."

Krishna Kant summarizes the balanced approach: "AI efficiency in small and less complex CS tasks with human connections on most of the customer touch-points will be key to the success of CS process and teams."

8. Value Realization Becomes a Core Operating Discipline

In 2026, helping customers achieve and recognize tangible business outcomes from your product isn't just good practice—it's survival. With customer budgets under intense scrutiny, CS teams must get serious about defining, delivering, and proving customer value throughout the entire journey.

Angeline Gavino frames the back-to-basics imperative: "CS teams will stop chasing every new motion and go back to basics. Leaders will get laser-focused on securing renewals first, especially with tougher macro conditions and more pressure on efficient growth. You can't grow NRR if the bucket is leaking, so retention becomes the primary growth engine."

She elaborates on what this means operationally: "Value realization will become a core operating discipline. With budgets under heavier scrutiny, your product cannot sit in the 'nice to have' category anymore. CS teams will put more structure around how they define, deliver, and prove value throughout the journey, so they can show clear business outcomes in every renewal and exec conversation."

Josh Schachter sees AI finally bridging the gap between what customers do in your product and what they achieve because of it: "Agentic AI will finally close the gap between product usage and customer outcomes. CS teams will be able to see value creation in real time, not just report on it after the fact. The best CSMs will shift from managing accounts to architecting value."

Looking Ahead: The Imperative for Action

Looking across these predictions from our industry leaders, several themes emerge with striking clarity:

• AI adoption is no longer optional. The winners will be those who implement purposefully, not just prolifically. The gap between AI-enabled and traditional CS organizations will widen dramatically.

• The CSM role is being fundamentally redefined from a product expert to a strategic business advisor. Those who can't make this transition risk being automated out of a job.

• Revenue ownership is the new table stakes: CS teams will own expansion forecasting with the same rigor Sales owns new ARR. The "should CS own revenue?" debate is officially over.

• Predictive analytics will shift from nice-to-have to mission-critical: With AI-generated value scores replacing traditional health scores, risk can be identified months before it becomes visible.

• The human element becomes more valuable, not less, but only for those who invest in developing strategic, consultative, and emotionally intelligent capabilities.

The predictions paint a clear picture: Customer Success in 2026 will look fundamentally different from today. The function is evolving from relationship management to revenue engine, from reactive support to predictive intelligence, from manual processes to AI-augmented operations.

But predictions are only valuable if they drive action. As you plan for the year ahead, consider:

• Where is your team on the AI readiness spectrum? The leaders who invest in AI fluency now will have a significant advantage.

• How are you developing your CSMs' strategic capabilities? Technical product knowledge alone won't be enough.

• Is your CS organization positioned as a revenue driver? The teams that can demonstrate clear revenue impact will thrive; those that can't will struggle for resources.

• Are you helping customers realize and articulate value? In a budget-conscious environment, “nice to have” products get cut.

2026 represents a moment of truth for the Customer Success profession. The predictions in this article don't just forecast change; they provide a roadmap for CS professionals and leaders to position themselves for success in what promises to be the most transformative year the industry has seen.

The question isn't whether these changes are coming. It's whether you'll be ready when they arrive.

We'd love to hear your thoughts on what 2026 has in store for Customer Success. What trends do you see emerging? What challenges and opportunities lie ahead? Share your predictions on LinkedIn and join the conversation about shaping the future of CS.

A special thank you to the CS thought leaders who shared their vision and helped us all better prepare for what's coming next:

Amber Monroe, Angeline Gavino, Chad Horenfeldt, David Karp, De'Edra S. Williams, Ed Powers, Guy Galon, Himanshu Garg, Josh Schachter, Julie Fox, Krishna Kant, Kristi Faltorusso, Maranda Dziekonski, Rod Cherkas, Stijn Smet, Victoria Shapira, Virginia Bloom

CS Mastermind #80 Transcript: Preventing Burnout and Maintaining Work-Life Balance

In fast-paced Customer Success roles, the pressure to meet targets, manage a growing book of business, and maintain high-touch engagement can quickly lead to burnout. When boundaries blur and reactive work dominates the day, it’s easy to sacrifice well-being in the name of customer outcomes. But burned-out CSMs can’t deliver consistent value; sustainable success requires protecting your energy and mindset.

This webinar will explore practical, actionable strategies for preventing burnout and preserving a healthy work-life balance. Prioritizing your well-being isn’t a luxury—it’s a requirement for long-term performance and job satisfaction in Customer Success.

In this CS Mastermind session, guest hosted by Kristi Faltorusso, Chief Customer Officer at ClientSuccess, our panelists discussed:

• Early signs of burnout and managing emotional fatigue

• Routines or habits that help reset and recharge during the workday

• Setting healthy boundaries with customers and internal teams

• Prioritizing workloads to avoid overwhelm

• Creating mental “shutdown” rituals to separate work and life in remote settings

• Tools or processes to help reduce task overload or context switching

• Professionally advocating for yourself when you feel overworked

This webcast featured:

• Josh Zamora, Customer Success Leader

• Keishla C. Jones, Managing Director, Partner Success and DEI ERG Leader at EAB

• Patrice Sawchuk, Customer Experience, Retention & Digital Strategy Advisor at Patrice Sawchuk Consulting

Top Takeaways:  

1. Burnout often stems from poorly defined roles rather than personal failure. Customer Success positions often become catch-all roles, with teams inheriting everything from product gaps to support requests. CSMs must establish clear boundaries for responsibilities to prevent CS from becoming the solution for all organizational problems.

2. High performance should be measured by sustainable outcomes, not heroic gestures. Organizations that reward CSMs for staying late, answering emails after hours, or taking extraordinary measures inadvertently create a culture where exhaustion becomes the norm. Celebrating efficiency and boundaries rather than sacrifice helps teams deliver exceptional results without depleting themselves.

3. Leaders must actively model the behaviors they want to see. When managers work around the clock or brag about answering emails on vacation, they send powerful signals that override verbal encouragement to take time off. The most impactful way to build a sustainable culture is to demonstrate that taking breaks strengthens rather than weakens performance.

4. Tactical scheduling changes can significantly reduce meeting fatigue and protect focus time. Simple practices like blocking 15 minutes before and after meetings, protecting lunch breaks with calendar reminders, and establishing a rotating meeting cadence prevent meetings from consuming entire workdays. These micro-adjustments create breathing room, helping teams stay energized and present.

5. Not every customer issue requires immediate human intervention or equal priority treatment. A balanced approach involves triaging accounts based on actual need, routing stable customers to self-service resources, and assigning dedicated coverage only when active projects or renewals require it. This measured response protects both team capacity and relationship continuity during transitions.

6. Regular audits of tasks and meetings reveal opportunities to eliminate burnout-causing busywork. Teams often perpetuate administrative requirements and reporting rituals long after they serve any real purpose, forcing CSMs to maintain systems rather than serve customers. Conducting quarterly reviews with questions like "what should we start, stop, or continue doing" helps identify work that drains energy without delivering value.

7. Early intervention depends on recognizing behavioral changes rather than waiting for crisis moments. Warning signs include missing deadlines, disengagement, scattered focus, difficulty sleeping on non-weekend nights, and consistently sacrificing personal priorities, such as exercise or hobbies. When teams feel safe discussing workload concerns early, problems can be addressed through adjustments rather than requiring recovery from exhaustion.

Session Replay

Session Transcript

NOTE: The following transcript has been edited for clarity and content where necessary to improve readability.

Kristi Faltorusso: Hello, everyone. My name is Kristi Faltorusso. Thank you so much for joining the SuccessCOACHING Monthly CS Mastermind webcast where we bring together professionals from across the customer experience ecosystem, from Customer Success Managers to Support Specialists and everyone in between. Today's session is brought to you by SuccessCOACHING, where they have helped nearly 40,000 customer facing professionals from almost 100 countries develop skills they need to excel. Whether they're in Customer Success, Support, or any customer facing role, you can find the right program for your learning style. You can find all the details from our offering on our website, successcoaching.com or in the chat where Ashley is kind enough to go and drop some links for you and any coupon codes that they're currently offering. CS Mastermind is all about real world expertise, so there's no theoretical frameworks or abstract concepts here. We're going to do a deep dive with practical, tactical advice and actionable insights that you can go and apply immediately.

Today's topic I thought was super timely given we're end of the year and I think we couldn't have a better group of professionals to help lead this, but today we're going to be exploring how to prevent burnout and maintain work-life balance, or as some of us have been discussing maybe work-life integration, but we will debate this. A few housekeeping items before we get started. We are recording this session. We will share the replay next week so sit tight, you'll have that in your inbox, so if you are working next week, be sure to go check that out. Please use the Q&A buttons for questions. Many of you are familiar if you've attended this before, there is a Q&A button in your toolbar. Go and drop any of your questions there. If you drop your questions in the chat, they may be redirected to go put into the Q&A.

We want to make sure that we have time and space to go and recall them at the end so we can get your answers for you. Anyway, you can also upvote them, so even if you don't have any of your own questions, but there's questions there, you can go and give them an upvote. We are going to prioritize by the ones that have the most upvotes, so please take some time, go scroll through the questions that have been asked and give a little thumbs up for the ones that you'd like to hear us answer and we'll get those prioritized for you. LinkedIn live viewers, feel free to go and post your questions directly in the comments. We're going to make sure that we get those over here as well. We'll keep the chat window today for commentary only, I hope, so please feel free to contribute to the conversation. I know everyone's going to have thoughts and opinions, especially on today's topic, so feel free to go and add to the conversation in the chat.

We have that being monitored, so we want to keep the conversation going. We'd love to hear the engagement there. For our guests, just we're going to get started. I want to have each of you introduce yourselves. We've got a wonderful panel today. And so we're going to go alphabetical in true SuccessCOACHING fashion and most of our panel today are returning experts and professionals, but we're going to go ahead and get started with Josh.

Josh Zamora: And I've got to go by first name, so it's very odd for me to go first on any sort of list like this, but-

Kristi Faltorusso: We're proud to give you this opportunity, Josh.

Josh Zamora: Merry Christmas to me. Thank you.

Patrice Sawchuk: I was just going to say, happy holidays.

Josh Zamora: I'm Josh Zamora. I am a Customer Success Leader. I've been in the Customer Success space for about 15 years now. Based in San Diego, currently in between roles, but that may be ending here fairly soon, so really excited to hear about some updates on that front here very shortly. But been doing this, love the community, love being a part of Customer Success. It's a great place to be. Love getting to meet new folks, so connect with me on LinkedIn. Looking forward to chatting with all of you. Thanks.

Kristi Faltorusso: Thanks so much, Josh. Keishla.

Keishla C. Jones: Hi, everybody. My name is Keishla Caesar Jones. My pronouns are she/her. I'm a Customer Success and Revenue Leader. I currently lead our partner success team for our digital experience, virtual tours at EAB. We support higher ed institutions helping students find their best life path, so really exciting to do that work. My work sits right at the intersection of customer outcomes and business performance. And so I'm a leader that really cares about creating sustainable opportunities, both for our partners and for my team members. And so I'm here because burnout is not a personal failure. It's often a systems' problem. And we want to make sure that we're consistently showing up with what we value for both our partners and who I believe is one of our number one partners as Success Leaders is our team members.

Kristi Faltorusso: I love that. And Patrice, last but not least.

Patrice Sawchuk: Hi, everybody. Patrice Sawchuk. I have been in the Customer Success space, similarly to Josh, 15 plus years before Customer Success was Customer Success. I've had the pleasure of leading large scale success functions for some incredible software companies. After taking some time off to be with my family, I am also searching for my next CS leadership opportunity, so a little plug there if anyone knows of any great opportunities. In the meantime, I did start my own consultancy, so I've got an amazing network of past employers and just network connections. Mostly advising on digital scale strategy. That's a big topic right now. AI strategy and tooling and automation. Super excited to be here today. It is a topic near and dear to my heart. I think it's really important so that we all ensure we show up as our best selves every single day, so looking forward to having a conversation today.

Kristi Faltorusso: I love that. And I know just from obviously watching all three of you contribute to conversations on social media and other podcasts and webinars, today's going to be a very, very thoughtful conversation. I'm super excited for it. Welcome everyone. Today we're going to do a deep dive into a topic that many of us privately but rarely in the open talk about, burnout in customer facing roles and the uncomfortable truth that the industry often treats it like a badge of honor. Let's be honest, somewhere along the way, being a team player started to mean answering emails at 10: 00 PM, taking on more accounts because, well, you're so good with customers or pushing through exhaustion because retention targets don't wait. We celebrate hustle, grit and responsiveness, but rarely do we celebrate boundaries, rest or saying no. And yet here's the contradiction. We expect customer facing professionals to bring empathy, energy, and strategic thinking to their customers while quietly ignoring the conditions that drain all three.

The reality is simple, but often ignored. Burnout, CS, Support, Service professionals cannot deliver exceptional customer outcomes. If we're burnt out, can't do it. And it's just not sustainable. It's not consistent and certainly it's not joyful. And this is the holiday season. We want to be filled with joy. Today we're going to challenge the narrative. We're saying out loud that protecting your mental health is not a bonus, it's a business requirement, that work-life balance isn't a perk, it's a foundation. And that taking time to care for yourself, it isn't selfish, it's the only way to take care of your customers long-term. We're joined by these professionals who have lived this. They've set their boundaries, they've created environments, and they know that while it wasn't easy, it was important. Instead of draining it, we want to understand how do we restore it, so we're going to dig in today.

We're going to talk openly and honestly, hopefully have a safe and engaging conversation around this, but we need to rethink what it truly means to succeed in Customer Success facing roles, so super excited to lead this conversation, guys. I think it's going to be great. Let's start with just a quick overall question that I'd love to hear from all of you, but do you think burnout is quietly normalized or even rewarded in Customer Success? And if so, how have you seen that show up in real life?

Keishla C. Jones: 100% it's normalized, Kristi. I think in one of the most common phrases, which I always cringe when I hear it, because I think it has some challenging roots, but just the way we talk about how we want to serve our customers, hyper responsive, white glove service, do what it takes. All those things create a environment where you feel like you can't say no, the customer's always right, all these different things. And that does create a sense where you put your CS in a servant position as opposed to a Success Leader position and it creates a lot of challenges and people will be willing to do things for the sake of upholding those mindsets.

Kristi Faltorusso: I mean, you're spot on. Josh, what are your thoughts?

Josh Zamora: I mean, I think that there's a glorification of the martyrdom, if you will, of actually doing this sort of work. If anyone who's going to bend over backwards to actually achieve specific outcomes for their customers, then they should put their personal lives on the shelf while they're doing this work. And it is very much normalized to actually have this sense of super heroics out of our professionals to do the work that they're getting paid for. And sometimes with a healthy dose of guilt that's added on top of it, if you don't. I think what I've seen in my career and even in most recent jobs is the sense that everyone's just got to get it done. Just get it done, make sure that you're putting all the effort to close out these deals, to close out these renewals without always recognizing that there's got to be some give and take on this as well.

Patrice Sawchuk: I think too, where I think this is a workforce problem, but I think where it gets hard for Customer Success is a lot of companies struggle to define the role of a CSM and draw the boundaries, the racy kind of whatever. And I think forever, the role of the CSM was to do whatever you can do to make that Customer Successful, make sure they renew, make sure they expand. And so I think the role in itself, if not carefully crafted, lends itself to being everything in the kitchen sink. And so I think we've all had roles like that where it just was not clear and everyone was shoving everything over to Customer Success. And so that just naturally creates that environment. And I think sometimes folks who set boundaries can be seen as rigid or not a team player. And so you get that dose of guilt that Josh mentions there. I think I've seen people exhibit really healthy boundaries and that's not always respected in the workforce.

Josh Zamora: And there's two sides to that too. Forgive me Kristi, but there's two sides to that, so it's number one, you as an individual setting the boundary for what I'm capable of doing, what I'm going to actually do, what I'm willing to do. But then also from a leadership perspective, what am I willing to hear from my team members about what they're capable of doing? There's got to be that mutual accountability that goes into play for a good work life... We were going to talk about it. It's work-life integration, not necessarily balance, but it's an important factor that affects everybody in the workforce, not just individuals, but the overall team as a whole.

Kristi Faltorusso: Now, I know that we're going to dig into this and talk about how the environment that we work in signals good behavior, bad behavior and all that. But just playing off, Patrice, because you've raised an interesting point here, but even I think each of you would probably share a similar sentiment that we oftentimes reward the folks that demonstrate these heroics, as you mentioned, Josh. And so even when you look at the folks who are being promoted into roles, into leadership, they're given new opportunities, they're given the cool, fancy projects, they're usually the ones that overextend themselves. They're the ones stepping out and leading out as the company would like them to, but really not protecting any boundaries of their own. I mean, what do you guys see in that regard? Or how do you think about it when you're even promoting or elevating their careers or giving opportunities to folks in your organizations?

Keishla C. Jones: I think, Kristi, it's challenging sometimes because those people who do those heroics over index whether or not those heroics were even successful, like were they the difference maker? Like we tell ourselves, "Oh, I brought the cupcakes to the meeting and that was the reason the customer signed the contract." And so we overindex on those things without evidence and data that those were the things that really changed the outcome, and is it something that we could repeat over and over again? And so I think that as a leader, one of the things I work to try to do is create an environment where people are going to excel the way they're going to excel, but my job is to have an equally yolked team.

Everybody's great at their job because I've supported them to give them their tools and then I give them the science to do their job and they bring their artist's mentality to it, their special sauce. But most of the times we throw our CSMs in the pit and be like, "Duke it out, figure it out for yourself." And then we wonder why we don't have good quality or things of that nature because we haven't standardized the things that need to be standardized. We haven't figured out what's the my pleasure moment in our customer journeys that we want to say that we're doing that with consistency so we don't find ourselves saying, "Oh, this person did this and got a result and this person did this crazy ridiculous thing and got a result, but maybe this was the thing you really needed to do and you did team too much."

Kristi Faltorusso: I think it's a very valid point. Josh.

Josh Zamora: From a leadership perspective too, I know I certainly struggle with the nine box mentality. Everyone that's seen a nine box, everyone knows what their... Especially if you're a manager at any period of time, you're going to have a nine box that helps you evaluate whether your team is doing the right things. It's really easy for us as human beings, and especially in a very urgent workforce to minimize the humanity of people into very specific performance metrics. And I like what Keishla's talking about here because what you're saying is that there's a whole human being involved with being a part of a team. And it's not just, did you accomplish these goals, but did you accomplish them in a way that you can say it's my pleasure, that it is something that I want to do and I am capable of doing this at scale with a repeatable process? There's got to be a more holistic view of our team members, of us as human beings, before we get into this purely performance-driven mindset. And I think that's going to facilitate more of that burnout normalization as well.

Patrice Sawchuk: I think too, as folks in leadership positions, it cannot be understated how much you need to role model what healthy hours, work-life balance. And I think sometimes as leaders, you have to burn the candle at both ends. And so it can be difficult, but I think we cannot underestimate that people are looking to us. And I think we've all worked for leaders that are just total workhorses and work 24/7, and then you're like, "Shoot, am I supposed to be working 24/7?" And so I think if you are a 24/7 worker as a leader, and that's just who you are and you're not going to change, I think it's important for you to verbalize to your team, this is not what I expect you to do and set really healthy boundaries for your team to set them up for success and their emotional wellbeing.

Kristi Faltorusso: That's a tricky one. That is a really hard one. And I've been coached many times on things like, Kristi, don't send the email, don't send the Slack, don't do the things, or talk to the team about why, or doing the things a certain way, so I do think it's important. I think this is actually a great segue to our next question here. Patrice, let's start with you, but can you remember a time when you realized your own workload or expectations had crossed the line from dedicated to unsustainable? And what were the signals that maybe you missed at first?

Patrice Sawchuk: I mean, I think when you're reaching that danger zone, I think the scales quite literally have tipped in one way or another. I think there has been times where we were talking about this before, but everything's urgent, everything's a priority, like I'm a maniac. That's how I know that I have over indexed in one direction or I am detached, I'm not motivated, I am not showing up as my best self. And that's telling me until I'm in center again, and that is the epitome of balance there. And I think it's not one or the other, it's kind of just how you are responding to those situations and just recognizing when you have fallen outside your center and your center is unique to you. And I think it's important to recognize what those signs are for yourself.

Kristi Faltorusso: Keishla, what are your thoughts on that?

Keishla C. Jones: This is going to be a tell me about a time when. I worked in an individual contributor role and I was a SME and part of my role was to deliver high stakes presentations for multimillion dollar opportunities. And I traveled all around the country. And one of the preferences, traditions, and requirements of this job, how they always did it was you would go in a day or two before and you would deliver your presentation in front of the internal stakeholders, ad nauseum, it was like a bad American Idol panel. It was just like, it's a no for me. And everybody's giving you feedback, say this, do that, do it that way. And as a SME, I was exhausted and most of the time I had delivered my best presentation to these people with no money, no signing contract power. And then I had to turn around and go do it for the customers, for the prospects.

And it was just the way it was done. And it was cruel, it was mean, it was hard. I mean, I could tell you that, did I get things out of it? Yes. Did I go through the fire and grow some thick skin and all that stuff? Yes. And then I happened to engage with a stakeholder once, I was going in to deliver her presentation and I'd set up my projector because I was all ready to do my show. And she was like, "What are you doing?" I was like, "I'm going to do the presentation." She's like, "No, I don't want to do that. Let's sit down and let's talk through each slide and I'm going to tell you what this customer wants to hear. I'm going to tell you what this prospect needs, what they told me in my discovery." And it was such a collaborative process and it was like amazing.

We did the presentation, won the deal. And we had won deals the other way, but it never questioned, is this sustainable, is it the right thing? And we were running the SME group into the ground doing this this way. And it was just refreshing to have somebody do something different and then realize that I could use that to set some boundaries for myself. And I think sometimes we find ourselves in workspaces and it's like, is it the way you've always done it and are you just doing it because of that and not because you've determined that is there another way? Is there a better way? And I think that creates more opportunity for better ideas. And in this world that we're in right now, the way we've always done it isn't going to hold up. And we really need opportunities for people to challenge the system.

Kristi Faltorusso: Well, that's a great story and a good example of that. Josh, what about you? Have you had a situation like this where you were kind of navigating your own imbalance?

Josh Zamora: Yeah, and this is actually my most recent role. I think like what Keishla was talking about, there's always the things that we've always done it this way. There's always processing tools that have been done a certain way. And I found myself waking up at 3: 00 in the morning or 4: 00 in the morning to prepare for something that ended up being kind of a non-event because just it's that artificial urgency. It's that artificial sense of doom and gloom that if you don't do it this way, you don't do it this certain process the right way, then you're going to basically fail. And what I found was that... And in this particular case, it was some reporting that I would do on a weekly basis and I would have to go and prepare for the CEO to show up and the chief customer officer to show up and I'd have all this data that I needed to talk about. And it ended up being like a 30 slide presentation for just internal note-taking for really something that could have been on a dashboard. But because it's always been done this way, I would stress about it.

And I noticed for me, the burnout point happened when I couldn't sleep the night before, my appetite was getting messed up. I was not having a good day before. The Sunday scaries were happening on Tuesdays. It was just that sense of dread around actually doing the things that needed to get done, not because they were bad in themselves, because there had been so much undue pressure put onto this thing that half the times most of the people didn't even show up to. But asking why we were doing it this way was never accepted. It was always like, well, that's what we do, so you just get it done. And I think that that was a good indicator for me that that's not a healthy way for me to actually be doing not just this work, but actually doing life in general. If I'm putting so much overemphasis on things that were not truly valuable or truly moving the needle in terms of getting some traction with customers or getting engagement for renewals or that sort of stuff, then I was just kind of wasting my time.

And that was a good learning moment for me that I've been able to take into looking for in new roles that I'm applying for.

Kristi Faltorusso: Let's offer folks some practical tactical advice here because I feel like we're thematically all saying some similar things, like it's always the way that it's been done, but how would you guys advise folks who are listening on how to manage up and how to challenge the norm in a way that doesn't threaten them? Because I feel like we all operate out of a place of fear. And especially if you're an IC, you don't have a leadership position, it is really hard for you to not be scared to challenge process and programs that have been designed by your leaders. What advice would you offer to somebody who's finding them in a similar situation to go and suggest, recommend an alternative while also helping that individual navigate their fear? Because don't forget, leaders are also operating from a place of fear a lot of times too, and we still need to figure out alternative ways, so what's the advice here guys?

Josh Zamora: I'll take the first stab at this because I think one of the things that helped me out, not just with that particular example, but in other occasions as well, get data to prove that this process is not working right. Using data is so important for this sorts of thing. You can't come into a meeting where you want to change a process without doing a little bit of preparation and readiness for that, so being able to come in and say, "Look, I get it. I know why we're doing this, but here's another alternative and here's what I've been able to do to make it work." AI is a great tool for that. It's a great, fantastic way to actually accumulate a bunch of data, tell a meaningful story, and then be able to present something in a efficient fashion that can help you change processes, especially when it's someone's baby and they are just overly attached to that process because they built it. Sometimes they just need a different perspective of someone telling them, "Hey, this is not the best way and here's what we can do a little bit differently."

Patrice Sawchuk: I agree wholeheartedly in that approach. I think the only other thing I might add in that storytelling, if you could anchor it to company values, outcomes, goals, that type of thing. And so you're tying it to a larger, more strategic objective, like we could do this differently. We can achieve this faster kind of thing that will speak to leadership and executives whenever you're tying to larger company goals.

Josh Zamora: That's not to say that ego won't get involved because ego is going to be a problem at some point there, but having the data, being able to tie it to specific outcomes and specific vision elements is going to be really helpful for that conversation.

Keishla C. Jones: I think Patrice and Josh, the thing that you guys are talking about is when you're trying to challenge big processes or systems that might be a part of your team's practices and behaviors, but oftentimes this level of getting over your fear of what some people like to call pushing back, and I kind of don't really like that phrase, to me, it's just about being a collaborative contributor to the work is to find it in those small ways. I had a team member a couple of years ago. It was one in one of my early leadership roles and inevitably things come up. There's things that you started your day and this thing pops up that you want people to do. And she did an excellent job. It took me a back the first time. I would say, "Hey, I got this thing, da, da, da, da. I need it, da, da." And she's like, "Okay, cool. I have these things that you asked me to do before." She would ask me what was priority.

We got shared understanding and she was excellent at doing it in a way that wasn't saying, "I don't want to do that or I'm trying to opt out of it or anything like that." But if you do it in the small ways and you give that good feedback to your leadership on a daily basis, it makes it a lot easier to build those practices and those behaviors for when you're trying to push at something bigger. And it's just small, like just saying, my team now, I would pop Slack messages and they're like, "Keishla, you're driving us crazy with the Slack." And they made me change my practice and my behaviors about how I brought messages to them in Slack and they said, "How you do it now is manageable." And so I think if you do it in those small ways, it makes it a lot easier to push on bigger things and have an input.

Patrice Sawchuk: I love that tip. That's such a great example. It's like I will work on the highest priority to you at this moment. These are the three things that are on my plate, help me to reprioritize with this new thing coming in. I think that's a great tip.

Kristi Faltorusso: All right, guys. Let's talk about a little bit more common practice that's specific to Customer Success because I think our space is a little nuanced compared to marketing and sales and product. What's one common practice that you all see in Customer Success, like always being available or taking on one more account? Or my favorite is when somebody resigns and you now have an entirely doubled book of business, but we treat that like a standard. It's just something we should expect will happen or can happen, but we also know that that's pretty harmful to someone's wellbeing when we are expected to just do these things, so how do you guys think about it? What's a common practice that we can do to not normalize this, but to address it?

Josh Zamora: I don't know if there's a silver bullet for these sorts of situations. I don't think there's any way to eliminate that situation happening because people are always going to move on. There's always going to be some need for new accounts coming in. And realistically speaking, from a leadership perspective, I'm not always going to have a really strong bench that I can pull from to bring someone up into a full CSM role. That said, communication is really the key here, so if you're an individual contributor, I want to hear whether or not adding that additional customer or bringing on some of those customers from the resigned team member are going to really impact you negatively.

And what those impacts are, if I hear that as a leader from my team and says, "Hey, this is going to really mess up these other customers because of this workload or this demand or here's what I need to take off as a result of it," that's going to help me be able to make a more informed decision for how I'm going to distribute those accounts and potentially make it easier for my team members to handle it. That's not to say that I'm going to avoid assigning those accounts, but it is going to at least help with finding a better balance there.

Kristi Faltorusso: Patrice, Keishla, any additional points there?

Patrice Sawchuk: Yeah, I mean, I'm trying to think of a... It's a compilation I think of a lot of the things that we talked about today already. I think it's the getting really comfortable or empowering yourself to set healthy boundaries, and to Josh's point and open up the lines of communication, I think that's early and often. I think the sooner you can make that your norm and the way that you operate and the way that you operate with your leadership team, then it doesn't feel really scary to have that conversation to Keishla's example, how can you help me prioritize this list? I would love that if somebody brought that to me. I, of course, want folks to be working on things that are highest priority. And so if that's not clear, I certainly want them to seek clarity there. And so I think the sooner you can generate that open and safe and honest working environment with your leadership team and setting those boundaries and asking them for clarity, I think those are really important and healthy habits to have across the board.

Keishla C. Jones: I think one of the biggest things that we've normalized as common practice and Customer Success is being the stop gap for all things. And it carries an amount of emotional labor, but oftentimes Customer Success Managers are covering for product deficiencies and they're standing in the gap, they're building hacks, they're building workarounds and things for partners and customers to use because we chose not to prioritize some product enhancement or some feature that we know is necessary. And that puts a lot of emotional toil on our Customer Success Managers. And then as a result, the wins and the losses really rest on them. I had a PSM a couple of years ago, she said, "I lost a customer today."

And I told her, I said, "You didn't lose a customer today. The company lost the customer today." And that means that there were a lot of factors of why that customer left, but it also means that when you win one, you didn't win it on your own either. There's a lot of reasons why that customer stayed. And so you've got to be willing to take both. And I think when we take a healthy look at that and don't make them feel like you lost, we lost, then it allows us the opportunity to look at those spaces where we are, once again, asking CS to be the Swiss Army Knife of all things.

Kristi Faltorusso: Let's talk about this because I think at scale, one of the things that we see very commonly in Customer Success is that someone on the team leaves. And they leave and then you have 10, 20, 30, 50 customers that need a home and it's really easy to give that to a top performer. And I feel like that's always an interesting dynamic is that, oh, well, you can handle this or this is something that you have, so we're going to give this to you because we know that you can handle it or you can do it or you're going to do a great job. How do we manage to that? How do we design more intentionally better processes and infrastructure so that that's not a common thing in Customer Success?

Keishla C. Jones: We take a tiered approach. I don't reassign every account when I have a gap and we're actually just dealing with that now. One of the things when we're doing short-term coverage, we take an all inbox approach to partners and we communicate them, "Hey, so-and-so's left the team. We are working on filling the space." For the partners who are sort of in homeostasis and there's no big things going on, we don't assign somebody. We say, "Come to tech support." The things that we want them to do anyways, we reaffirm the self-service ways and things like that and how we're working in the gap. If you need something, come here. And then the partners who might be in renewal, we assign those out because they're in some sort of active space or where there's an active project, so I think there's a way as leaders that you don't have to take a book and reset them.

You can allow yourself to hold them with the team and then we triage for the moment and then you're not reintroducing them to somebody else to then reintroduce them to somebody else. That gets confusing too. And so we take a very triaged approach and we only sign out by name where there's commercial situations going on, an active project or some other reason for that partner to need somebody for six weeks or whatever that might be. And I think it's a reasonable thing that partners can understand.

Patrice Sawchuk: It's a terrible customer experience to assign somebody temporarily. It's like, I just lost this person that I love and now I'm going to meet Josh for two months until someone new comes on board. And it's just like a ping pong, so I think that's a really great approach to prioritize the must haves. And then everybody can just sit in harmony for a little while as long as they have somewhere to go.

Keishla C. Jones: Yep.

Josh Zamora: And I think it boils down to not everything is priority, not every customer is priority, not every issue is priority, so figure out which ones are, work on those. Everything else can sit for a little bit. It's okay.

Patrice Sawchuk: Yeah.

Kristi Faltorusso: It's not unreasonable to set that expectation with anybody.

Keishla C. Jones: Anybody.

Kristi Faltorusso: Customers or internal or anybody.

Keishla C. Jones: And I think that helps us to level set with our customers. When we do heroics for our customers, heroics don't become heroics anymore. They become the norm.

Josh Zamora: The standard.

Kristi Faltorusso: That's the baseline for how we can help support them.

Keishla C. Jones: They're always rushing to them. It's like the baby who you rush to them and then they weren't going to cry until you went... And then they cry. It's like, so let's just calm down.

Kristi Faltorusso: All right. Well, so let's talk about mindset because... Oh, I'm sorry, Josh. Go.

Josh Zamora: Real quick, I just saw Nicole's comment in the chat and I wanted to address that real quick because as a leader, this is something that I feel very personally about. As a leader, I need to be mindful enough and sensitive enough to my top performers so that I'm not putting so much on them that they don't stay as top performance. I need to act as a shield for my team in some cases where they're getting overloaded or getting overworked and they're not able to do their best because if we want them to continue to be top performers, then we got to make sure that we're not overloading them to the point where they can't handle it, so if we're getting to that point where I can't take this on and that's viewed as a negative thing, then I as a leader have potentially have not done a good job of protecting them from that mentality.

Keishla C. Jones: I think even in doing that, that can create a dynamic in your team where people sort of withhold because they don't... If being a top performer just gets you more work.

Josh Zamora: No good deed goes unpunished.

Keishla C. Jones: I want to keep my head down. I want to protect myself. And that doesn't benefit the team, right?

Josh Zamora: No.

Kristi Faltorusso: All right. Well, let's talk about mindset because I do think that that plays a big part in what we're talking about here. Let me open this up to the group, but if you could change one mindset across the industry about what it means to be a high performer in Customer Success, what would you change and why? Keishla, go first. You're burning to contribute here.

Keishla C. Jones: I'm not burning. I had something that I'd noted. I think one of the... High performers don't mean that customers love you. It's not just about adoration, it's about progress. And so sometimes because we are so deeply attuned as CS professionals to the relationship we spend a lot of time cultivating what feels like good congenial relationships, and we mistake that for a healthy partner, for progress, for value realization. And even a high performer who's producing commercially could be masking health problems. And so I think it's just really important that we understand what... High performance can get rewarded, and it's maybe not the thing that's healthiest for the business. You can have somebody that's a high performer individually, but they're not necessarily always helping the business outcome, so I think that's one mindset that is important to connect, that how do I serve the customer and the business at the same time?

Josh Zamora: I would probably go back to what I said about the nine box earlier. I don't think all performers are created equally, and measuring CS on a sales methodology for performance is not ideal. Same with measuring support on a CS performance track. There's got to be some level of specificity to how we measure different departments and what the goals and outcomes are. And I think that that's a mindset that I think probably just needs to shift over time. If we're going to see CS or support or onboarding or any other team actually do well is that we're measuring the right things for the right people. Same as we handle our customers. We don't treat all our customers the same. Why are we treating all our employees the same? And I think we need to have some level of adjustment to the way that we measure what performance looks like, especially in CS.

Patrice Sawchuk: I think I believe very strongly in data and metrics and tracking and things that people can really understand and that often tends to be just one piece of the picture. And so I almost think about it as quantitative and qualitative or what you do and how you do it, finding that right balance. And it can be tricky because when you're doing performance management or those types of things, they want you to be super quantitative because you don't want to introduce emotion and feeling and opinion and biases, but the data and the metrics don't ever tell a whole human story, like humans aren't built on data and metrics. And so I think it's definitely a piece of it. It's the checks and balances. Are they doing the things and delivering the outcomes? But there's also the, what type of contributor is this person to your culture, your team? Are they making people better? Are they mentoring? There's all those other things that are more like the qualitative and the how they show up and work that are hard to measure, but a huge piece, I think, for measuring high performers.

Kristi Faltorusso: Patrice, I think you called on something that we don't double click into enough, which is the how did you get there because there's a lot of ways to get a lot of places. And if you are finding that people are overextending themselves or really creating these unhealthy working situations for themselves because they believe that getting to that outcome is at all costs. It's that mentality of at all costs, then obviously that's not what you want to reward, but might be the person who's doing it most efficiently.

Josh Zamora: And think about it in the context of a top performer, you're always going to put new people under them to be trained by them. And if they're doing heroics and if they're doing the stuff that actually burns them out, you're basically perpetuating that same behavior. I don't want that in my organization.

Kristi Faltorusso: How do you guys spot that? What are you looking for?

Josh Zamora: I think Keishla talked about it a little bit earlier. It's the art and the science of Customer Success. We can provide the science of these are the things that you should be doing consistently. Here's the playbooks, here's the processes. I want to be able to track that people are doing those things appropriately. And we have all the metrics and the dashboards for that. But then the human aspect of it, the art element of it is sitting in on their calls, being able to listen to their recordings, being able to have debriefs with the team members around what did they do? They did the mechanics of it, but what's the art that they actually accomplished as part of engaging with customers? Those can be really easy to find if you're looking for them. And when you create the right... We used a tool at my last company called Realm, and it allowed us to actually do an AI analysis of any call.

We'd randomly select a call, we'd run a simulation and we'd score it based off of not just the key mechanics of did they solve the problem? Did they actually address a core outcome? But was their tone good? Did they actually have a friendly banter? Were they actually having a good relationship? And as much as AI can pull that up from a transcript, then going and listening and verifying, oh yeah, they've actually got a good relationship going there with that customer. And then we can go into their notes and see, all right, did they actually put in the right information? Are they able to sense the softer skills of what's needing to happen for this particular account? If you look for it, you can find it, but that's a habit in leadership that you need to get into to actually look for those elements is as part of your team's development.

Keishla C. Jones: And I think as leaders, all of that, I co-sign on that and being on calls, not just the escalation calls, join just regular business as usual type things to see what most customers are experiencing. And then I would add creating a culture. Both of my team leads do a really good job of just creating a culture of shared commentary and problem solving within their teams. And so we'll bring a problem to the team. Let's talk about it. Let's work it, shop it together, let's do a postmortem. And so creating that safe culture to say like, "I did this. Hey, I could have done this differently or I did this really well." And creating a good culture of feedback is really important as well.

Patrice Sawchuk: And I think when you find those folks or those examples, it's so important to celebrate them in many different ways. I don't think we do enough celebration across the board. And I think that a peer role model is so much more influential than me explaining how to run a call or how to do this or that or how to handle a tricky situation. And so one of my favorite things is just spotlight that person in a team meeting and have them walk through it and it gives them visibility. And then they are quite literally propped up as a role model for the team.

Keishla C. Jones: And you're using your time as a team to reinforce that best practice, not that practice that's... Let's not celebrate the crazy thing that you did to get it done. We want to acknowledge it, "Hey, we had to do something crazy to get it done, but that's not something we want to perpetuate and standardize."

Kristi Faltorusso: That's a great point and the differentiation between that, acknowledge it, yes, and don't celebrate it because we don't want people to think that that is how these things should get done. That's not what's rewarded. All right. Well, listen, we know technology plays a big part in all of this, so I'm curious to hear how you're thinking about technology either helping or contributing to burnout, especially in Customer Success. What are your thoughts here?

Patrice Sawchuk: Both. But we're in control of it. I think there's the always on component that we are 100% in control. And so if you have your work email and Slack and all of that on your phone and it's family time on the couch, those notifications should not be pinging you. Don't get into those really bad after hours habits. I think the downside is the always on stuff, especially with remote work. It's really hard to set boundaries when you're not physically going to and coming home from an office. But I think the flip side of that is there's a lot of really amazing tools evidenced by all the note takers that are in attendance today that also help us to be a lot more efficient.

All the amazing AI tools out there, it's a really exciting time, all the stuff that's kind of making its splash in our space. And I think with the right tech stack and set of tools, we can be so much more efficient, but that does not mean we're taking on more. And so it's like, I'm going to have AI work on this outline while I check these things off my list, or I'm going to go take the dog for a walk while AI is running something in the background. And so I think it's all within our control, the bad side of things, we have to have discipline.

Keishla C. Jones: I think all the tech tools obviously and the mobile nature of things post-COVID has created that always on mentality that you talk about, Patrice. And so I do things to sort of ease those boundaries, so my email platform and my Slack are on my phone, but I don't have notifications. And so if I choose to interact with work on my telephone and not at my desktop, it's an act of choice and not because the technology is prompting me to act or do something because I don't know about you guys, when I have the little numbers, the numbers have to make them go down, they have to go away.

And that's the gamification of it all. It's built and designed that way to get our attention. And so I think encouraging your team, and I think it's also equally important, especially when the company's not paying for your phone to recognize to your team, "I'm not asking you to do that. I'm not asking you to be available in this way. The company gave you this device to be available and these reasonable working hours to be available." And so I think it's really important that you make sure that you model what you expect. But for me personally, one of the things that I did do was turn off notifications and it's really helped ease that tension.

Josh Zamora: I think I'm going to say two things. Number one is yes, technology certainly facilitates that always on mentality, but I think the component of it is the cult of, especially SaaS companies, the cult of SaaS where we're like, "We got to get this done. We got the next great thing. We've got the next best thing that's going to be out there on the market." It can be really easy to get cultish in the companies that you work for. And I think that technologies just helps facilitate that, the gamification, the way that it's always on, the way that it's always available. I think there's also the second part that I would say is that there's a mutual accountability component to it too as well. How do I want to say this? It's really easy to rely on technology to be a way for you to maximize your impact and maximize your efficiencies, but it can also be used as a shortcut or as a crutch for your inefficiencies as well.

Technology can be used effectively, but it can also be used really, really badly to promote the wrong behaviors, so I think it's important that we are creating a structure of mutual accountability with our team members, with us as leaders, but also with them holding us accountable, so when I go on vacation, I'm not going to be responding, even though I have it on my phone. When I go on time off, I'm not going to be answering my emails. I had a former boss that would go on vacation and he'd brag all about, "Oh yeah, I'm in the middle of the Caribbean and I got the internet package so I can continue doing work and I'm going to keep checking on everyone's work." It's like, that's not sending the right message, so hold yourself accountable to the fact that you are going to actually take some time off because that's going to speak volumes to your team members as well, so don't use technology in a way that's going to facilitate that negative behavioral pattern.

Keishla C. Jones: I think the other side of where technology shows up in CS, aside from just sort of this always on mentality is, what's in our tech stack to help us do our job? And sometimes we uphold things in our tech stack. And so we're doing the tech stack thing and not necessarily the thing we need for our work. It's like, I don't want you to wake up and do Salesforce today. I want you to use Salesforce. That's not your job. And so I always try to tell my team, I want you to document what you're doing, but I'm not asking you to be a historian. And so what's that sweet balance and how are we making sure that what we're asking, there is an element of data that has to be entered by our CSMs, we have to keep track of certain things, but really audit what you're tracking in every... And if you add something, look and see, is this fitting?

And so we are constantly saying, okay, we might've started doing this because we needed to solve a particular problem. Do we still have that problem? Is it still a need? I would really spend time checking. And when your teams feel like they have work to do because it's a task to do to uphold the system and not really do the work, that can create an environment of burnout. And it's something we struggle with, but we try to keep it top of mind, so when we're adding something to, what is that serving and what is that helping us to get to? What's the data point? What's the information?

Josh Zamora: The cult of SaaS and the sacrament of Slack, they absolutely go hand in hand sometimes.

Kristi Faltorusso: Very good. All right. Well, let's pivot. I want to ask one last question before we open it up to Q&A because I think leaving people with practical tactical advice and guidance and hearing from you guys as experts and what you've done, I'd love to hear your playbooks. If you lead a team, which I think that you all have if you're not currently, what's one system or a change that you made for your team, for your people to reduce burnout?

Josh Zamora: One thing that I did was we didn't have PTO at my last company or we didn't have unlimited PTO in my last complete.

Keishla C. Jones: I was like no PTO?

Josh Zamora: We did have PTO. I'm sorry.

Kristi Faltorusso: It was 24/7, 365.

Josh Zamora: Yes, exactly. It was really great. We introduced PTO, burnout solved. No, we had limited number of hours, and what I would do is I would have access to everyone's PTO and go through on a monthly basis, on a quarterly basis, where are you at? Did you take vacation? Are you actually taking time off for yourself? And that was part of a quarterly business review with my team members during our one-on-ones to look at what they're actually using for their own mental health.

And obviously, like you said earlier, Keishla, there's seasonality with work, so if it's the busy season, no, we're not going to do that right off the bat. But if there's a little bit of a lull and someone hasn't taken off any time in the last three months, what the hell? Go take some time off. Go enjoy some time where you're not actually doing this work because I want you at your best when you come back. And that actually helped a lot is showing the team that I was viewing that and prioritizing that as a part of their wellbeing, not just have they hit the retention targets, but are you actually taking time for yourself? That was a big thing.

Kristi Faltorusso: I got to piggyback on this before we move on, but a lot of people don't want to take PTO or time off because they don't want to come back to double the work. And so I know that there is a lot of people out there that feel like it's not even worth it because I won't... The time coming back will be worse than the reward of the time off, so what are your thoughts on how do you manage that? How do you create the systems in place so that when they come back they're not feeling so overwhelmed that it wasn't worth it?

Josh Zamora: One of the things that I like to say... I'm sorry, Patrice.

Patrice Sawchuk: No, go ahead.

Josh Zamora: One of the things I like to say is that no one's dying on an operating room table because we didn't put in our Slack notes, we didn't put in our Salesforce notes. Yes, that's critical for getting stuff done, but it's a reminder. It's always a reminder to the team that yes, this is important, but it's not the most important. Yes, there's going to be a ramp up coming back, but we'll help as a team, and that's where we get some additional coverage. I know person A is going on vacation for a week, I've got person B that's going to help step up and handle some of these things, and then they can do a debrief whenever person A gets back, so having that overlap in people does help a lot. Sorry, Patrice, I interrupted you.

Patrice Sawchuk: No, no, that's fine. I was just going to say unlimited PTO is death to PTO because without a bucket to decrement from, it is really hard to get people to make sure they're taking it. And so I agree. I think it's having a mechanism if you track time off or time off requests or not, I think it's super important to make sure people are taking time off and telling them you need to take time off and you endorse it. I think to the point of being afraid that there's just too much to clean up from when you've taken time off, I think we have to really make sure, and this is more a leadership thing, but I am seeing this transform quite a bit. But old days CS was so human led, so reliant on an individual and we have to get out of that. And so I think the more self-sufficient customers can get, to Josh's point, there is nothing they're going to miss out on.

No one's dying here. And so I do think we have to generate systems so that customers can get what they need so a human doesn't... Because how are they going to do it while you're on back-to-back calls anyway? I think we have to get out of that reliance 24/7 on humans being available for burnout purposes, but also so people can go and take time off and not have to worry about cleaning things up. I mean, if you've taken extended time off, I would say carve all those emails out, put them in a folder, start fresh. It'll come back around if it's important. Do not dig out from a massive hole.

Kristi Faltorusso: Keishla, what are your thoughts? What's your playbook? Because I know that you've designed a lot of systems in place to help your team. And so what's your top one?

Keishla C. Jones: My top thing that I think I've changed in response to burnout... I have two, I'm going to share. One piggybacks on this. And I have a calendar wellbeing reminder that is on my team's calendar once a month, and it reminds them to block lunch. PTO is great, but eating every day, I'm going to tell you, not an underrated thing.

Kristi Faltorusso: And not at your desk.

Keishla C. Jones: Not at your desk, right?

Patrice Sawchuk: Yeah.

Keishla C. Jones: Put a recurring thing on your calendar because you can move your lunch, but if you don't remind yourself to take it's very easy for your calendar to get filled up. I talk to them about protecting their time before and after meetings, so as soon as you book that meeting, block the 15 minutes before and after, you know you're going to need it just to just decompress, just to kind of come off the things. We block focus time on Friday afternoon. I think there are small, those micro things that you can do all the time. I co-sign on all things about the PTO behavior. The other thing I changed was my meeting cadence. We used to meet every-

Patrice Sawchuk: Yes.

Keishla C. Jones: ... two weeks for types of meetings that we met as a whole team. I did an audit of my meetings. I did a little bit of research. It says your internal time as a PSM should be in the 20 to 25% range somewhere in there. And that is internal that is not about working on something that is a billable hour, like you're working on something for a customer that you can name. If you're doing things broadly, and I did an audit and we were sort of in the zone, but how we were using our meetings wasn't the most efficient. And so I changed to a meeting cadence week one of the month is cross-functional. Week two is commercial. Week three is service and we take week four off. And then we do that cycle and it has really cleared up. The team understands the purpose of the meeting. They understand our focus and it has just made us better.

Kristi Faltorusso: I love that. All right guys, we're going to move to Q&A unless anybody has one more thing if anyone wants to add. I don't want to shortchange the conversation.

Patrice Sawchuk: No.

Kristi Faltorusso: All right. Very good. For those of you who have hung out this long, thank you so much for sticking with us. We're going to open it up to Q&A, so I'm going to ask that you take a couple of minutes. If there's anything here pressing that we talked about, something that you have a question about around burnout, please head over to the Q&A, drop your question in. We do have one to get us started, so I'm going to open this one up to the team here. What would you say the best first step to move away from this would be? It can feel overwhelming to solve this huge problem, but what's your recommended first baby step?

Josh Zamora: As an individual contributor... Oh, I think I'm asking a clarifying question though, but is it individual contributor or as a manager? Because I think there's different baby steps that can be taken on either side of that.

Kristi Faltorusso: Let's say the baby step ... Okay, that was a manager. She clarified for us. Thank you.

Josh Zamora: Thank you. As a manager, I think what was just being talked about in terms of setting time aside, making sure that, like Keishla has it on her calendar, checking in for wellness. Those are little things, reminding for lunch, taking a walk, doing little things that as a manager you want to remind your team to do, but then also that you as an individual are actually doing as well. I have for my own personal calendar, whenever I have it in work, I have an hour blocked out for every day for a workout. Whether I go work out or not, I actually have that time blocked off. It's sacrosanct, it's protected. It is not available for meetings. If it is something that it's super urgent, I will move that around. But very often I'm keeping that time even just to go and sit down for a little bit and get away from my computer, so I think that that's an important thing that I model for my team and that I want my team to actually be able to do for themselves as well. Again, Patrice, I interrupted you again.

Patrice Sawchuk: No, I think that just to dovetail off of that, I think as leaders, we cannot underestimate how powerful modeling that behavior is, but also I think verbalizing the ideas. And so I think it's putting the systems in place. Like Keishla mentioned, making sure everybody knows that it is endorsed and encouraged to do these things. And look, I am doing them too because I think sometimes we forget how much folks shy away from that. And if they see their leader doing it it's creating that permission and you get out of the habit too. And so if you continue to role model it, they'll see it and it'll be a sign for them that it's a safe space.

Keishla C. Jones: I love that. I would say my first baby step is to audit. Check yourself, ask, so go and ask about... I did an audit one time, I just said, operationally, here are the sort of the worksheets we have. What are the things that we ask you to do? And I made them make a list for me, and just to see it on paper, these are all the things I ask you to do once a month, twice a month, two times, every other month, whatever that might be. Find out what it is you're asking them to do that you can then say, is that still serving us? Do we still need that action? The second thing is do periodic start, stop, continues with your teams. Just openly say, "What are we doing good?" Everything's bad, so you can say, "Okay, the things we're doing good, we want to make sure." Because sometimes you can be doing good things and you don't know it and you're not getting credit for it. And what do you need to stop? What do you need to continue?

Patrice Sawchuk: I love start, stop, continues.

Kristi Faltorusso: Do them with your customers too.

Keishla C. Jones: Yes. Yes, 100%.

Josh Zamora: 100%.

Kristi Faltorusso: I'm sure there's things that they would like us to stop doing.

Keishla C. Jones: What are you asking me for constantly? Please stop.

Kristi Faltorusso: Very good. All right. Well guys, I'm going to open it up just to see final call for questions, so if anybody has any additional... Oh, we got another one. What specific signs do you look for to identify burnout early, both in your teams and in yourself?

Patrice Sawchuk: I mean, I think I talked a little bit about this before, but I think it's change in behavior. I think you know what's normal for you and I think you know your team best. And so I think you can tell when somebody's off. And I think it's really important to... You should not ignore the signs. And I think I would rather ask and they'd be like, "Oh no, it's totally fine. I was actually just tired this morning." I'm like, "Okay, just checking in." And I think people will appreciate that you're doing a little wellness check with them. And so if they're usually super upbeat and talkative and they're not, or if everything seems really erratic or if they seem disconnected, so I think it's whenever they're acting off or their behavior is different, just doing a wellness check-in. I've just noticed whatever and make sure it's very gentle and it's coming from a really good place. And best case scenario, they're just having an off day. But maybe you uncovered something and then you're opening the door to have a really safe and healthy conversation.

Keishla C. Jones: I would look for somebody that's missing deadlines, like if there's somebody that's consistently not... If everybody else is kind of doing it and they're not, that might be a concern for me. Asking obviously I think is tops on that, Patrice, but I would look for disengagement. Sometimes the burnout shows up as disengagement as well.

Josh Zamora: I don't have anything meaningful to add because both of those are exactly right.

Kristi Faltorusso: I will add to my self-reflection because I think it's easy to go look at these things in our team, but for me, I know things like exhaustion is different than tired. When I'm exhausted that is a signal that I am hitting a wall for myself. Am I sacrificing the things and the things that I enjoy? If I'm finding that four out of five days a week, I'm not getting in a workout or four to five weeks, I'm going to bed with a laptop in my bed. Those things are signals that something isn't working right, so I think it's also important for you to look at your own habits and your behaviors as well as your personal priorities and understand where you're making sacrifices.

Now, I will say as a leader, and I'm sure we can all attest to this, there are moments and times and days and projects and seasons where things have to get done and they don't happen during the 9: 00 to 5: 00 hours, and that's okay. But when you're noticing that these things are becoming more of the norm and not the exception, that's when you have to start checking things, so it's okay to go above and beyond periodically when something needs to happen. There's a big escalation, a big deal coming through, absolutely. But if that is the standard expectation for you, I think that's where you have to start having conversations with yourself and the teams around you.

Josh Zamora: Like I said earlier-

Keishla C. Jones: Oh, sorry. I find for myself a sign of burnout for me is when I'm not focused, when I can't... Because I've multi-tasked to the umpteenth degree and I'm like my train of thought or I'm not remembering things and it's because, oh my God, I'm doing too much and I need to back off a little bit and take a step away, so I think that's a good reminder for yourself.

Josh Zamora: The thing I'll add is what I mentioned earlier was the Sunday scaries happening on other days. I think that's a really good indicator for me. I'm like, oh yeah, this is really weighing on me for whatever reason. Can't sleep. Eating goes differently. All the different things that my body tries to tell me like, "Hey, you need to knock this off and try to get back to a homeostasis point."

Kristi Faltorusso: All right, very good. We've got one more question. When working remotely within many time zones, what's the best way to manage burnout for a team and the expectations for clients to respect their working hours to avoid burnout?

Josh Zamora: I worked with the global team, my last role. I had folks in the Philippines, in Australia, in the UK, all over the place. And one of the things that I really wanted to do was to make sure that everyone was able to get in and out at the right time based off of what their schedule allowed. There's a couple of things, starting at the very top, organizing customers based off of time zone. The structure of how customers are assigned based off of time zone, based off of what available hours there are. It's never going to be perfect, but at least trying to approximate that, does help a lot. And then as a manager, honoring the fact that, hey, it's two o'clock here in San Diego, but it's already 10 o'clock PM in the UK, I'm not going to be reaching out at that point in time, and I'm not setting the expectation that they should respond to me when it's that late in the evening.

Being aware of the time zones is really, really important just as a baseline expectation and then working hard to honor that for my team and then allowing them to set expectations for their customers as well that, "Hey, I'm working in this time zone, here's my hours, here's when I'm available." I think customers on average are very receptive to clear communication because that's a kindness, so when you are showing that you are kind to your customers and saying, "Here's my available hours and here's what I'm capable of doing during that time," that solves 90% of the problems. And then when it truly is an urgent issue, it can be treated as a truly urgent issue, not as the norm, so allowing my team to feel empowered to do that is important.

Keishla C. Jones: Empowerment is huge and to do what makes sense, so we generally orient ourselves to East Coast hours, but we have West Coast customers, we have international customers. And so if I have a success manager who is an East Coast person who does a 7: 00 in the evening call for a West Coast partner, then I don't expect them to start at East Coast hours and make sure they know that. Or they take a break in the middle of the day to accommodate for that time, so adjust accordingly where those things come up, but feel empowered to manage that customer relationship, but also to do what makes sense. I'm not asking you to do a seven o'clock call and start work at 8: 30 Eastern at the same time. Those two things don't have to coexist.

Patrice Sawchuk: Agreed.

Kristi Faltorusso: All right. That was our last question. All right, so unless somebody squeaks one in, I'm going to go and close this out. All right guys.

Keishla C. Jones: Thanks everybody.

Kristi Faltorusso: Well, I think that we're safe to wrap up today's session, but super grateful. We've reached the end of the session and want to just thank all our guests for sharing valuable insights and experiences, so Keishla, Josh, Patrice, thank you guys so much for being a part of this conversation today, sharing your expertise and your experiences. Obviously, it's your contributions that made this conversation so meaningful and hopefully everyone who attended today got a lot of value from that. To our audience, thank you so much for your active participation. Obviously, share your thoughts about today's session on LinkedIn, go tag SuccessCOACHING, tag the guests, follow up on these conversations.

Maybe there's something privately you want to ask, something that is a burning question for you, feel free to reach out to our guests here privately. I know some of these topics can be sensitive in nature, so if there's something that's going on in your universe, please feel free to reach out and make a friend. But finally, let me leave you with this. Great customers are focused individuals, they know that they don't have all the answers, but they know how and where to find them, and that's why we've created this series, so thank you guys so much. Have a great rest of your day, a great month. Happy holidays. I hope everyone has a lovely holiday, safe, happy, healthy new year, and we'll be back in 2026. Thank you all so much for participating.

CS Leadership Roundtable #60 Transcript: Delivering Personalized Customer Experiences at Scale

Customer Success teams are expected to deliver highly personalized experiences to increasingly large and diverse customer bases. But as organizations grow, the challenge becomes: how do you maintain that personal touch without exhausting resources or sacrificing quality? Without a scalable approach, personalization efforts can become inconsistent, inefficient, or altogether abandoned, putting retention and satisfaction at risk.

This webinar is essential for Customer Success professionals who want to strike the right balance between efficiency and empathy. By using practical frameworks and tools, CS leaders can help preserve the human element while driving strategic growth and repeatable success across customer portfolios.

During the live CS Leadership Roundtable, the panelists discussed:

• Effective automation tools that still allow for a personal touch

• Maintaining consistency in personalization across a growing customer base

• Ensuring personalization doesn’t become superficial or robotic

• Balancing high-touch and tech-touch approaches across different segments

• Mistakes teams should avoid when trying to scale personalized experiences

• Measuring the impact of personalized engagement on retention and expansion

For this CS Leadership Roundtable event, host Andrew Marks was joined by:

• Brandon Deleeuw, Senior Client Success Manager at VisualDx

• Cole Jacquard, Head of Customer Success at ReelData AI

• Michael Weil, Senior Manager, Customer Success at Scale at Salesloft

Top Takeaways 

1. Personalization at scale means automating responses to customer behavior while reserving human intervention for moments that matter most. Use technology to detect patterns and trigger relevant actions based on what customers actually do, not what you assume they need. Then layer in strategic human touchpoints at renewals, adoption drop-offs, or value realization milestones, where empathy and expertise create outsized impact.

   2. Treat customer journey maps as flexible frameworks, not fixed pathways. Break journeys into micro-moments (onboarding, feature discovery, usage drops, renewals) and design flexible responses for each. Designing for variations instead of a rigid, ideal path creates personalized experiences that adapt to actual customer behavior.

   3. Not every customer wants high-touch personalization. Build choose-your-own-adventure engagement models with strong self-service options, community resources, and opt-in human touchpoints. Relevance and reduced effort often matter more than intimacy when scaling personalization across different customer personas.

   4. Office hours and vertical-specific roundtables enable personalization through structured human moments where customers drive the conversation. A small CS team can manage thousands of accounts by hosting regular CSM-facilitated sessions where customers with similar challenges connect with each other. These gatherings deliver genuine value while remaining scalable and authentic.

   5. Set expectations early about how engagement will evolve throughout the relationship. Start with weekly or monthly touchpoints during implementation, transition to quarterly check-ins as customers gain confidence, then move to on-demand availability. This prevents comfort-blanket meetings while building customer confidence to succeed independently.

   6. Build hybrid models that deliver both deep personalization for high-value accounts and scaled engagement for the full customer base. High-value accounts need genuine personalization to protect revenue, while smaller accounts need sufficient support. Combining automated relevance for all customers with layered personalization for strategic accounts delivers scalable experiences that drive retention and growth.

Session Replay

Session Transcript

NOTE: The following transcript has been edited for clarity and content where necessary to improve readability.

Andrew Marks: Awesome. Welcome to the CS Leadership Roundtable, your monthly forum for actionable insights across Customer Success, Support, and Service. I'm Andrew Marks, co-founder and architect of the SuccessCOACHING training program. And I'm thrilled to be leading today's conversation on delivering personalized customer experiences at scale. This learning series is brought to you by SuccessCOACHING, where we've trained over 40,000 professionals across 96 countries. Whether you're focused on Customer Success, Technical Support, or Frontline Service, our programs are designed to help your team deliver exceptional customer experiences. You can find all the details of our offerings on our website, successcoaching.co, or in chat, or Ashli has provided some links and any coupon codes that we're offering.

We're also looking for your input on next year's webinars topics. You can put that back in there. We're looking both for ideas of the webinar topics. We've only locked in the first three. So there's still some jockeying going on. We're also interested in whether you want to participate in this webinar. So please click on that link that Ashli has just thrown up into chat to tell us more about what you're interested in hearing about and if you're interested in being part of it.

And before we dive in, I want to share some exciting changes to our webcast coming in 2026. We've been listening to your feedback and we've heard that the line between leadership challenges and practitioner challenges isn't as clear as we thought. The best CS professionals are thinking strategically regardless of their title. So, starting next year, we're evolving CS Mastermind to bring everyone together into one powerful monthly conversation. We're retiring this CS Leadership Roundtable as a separate series, although the recordings will still remain on the website. And we're folding those leadership topics right into our CS Mastermind. So this means every session will have something valuable, whether you're leading a team or you're an individual contributor looking to level up. And we think this creates even richer discussions, leaders sharing organizational perspectives and practitioners bringing real-world insights from customer interactions. And that's where the magic happens. So, more details coming soon.

A few quick housekeeping notes. This session is being recorded and will be available next week with a transcript. Use the Q&A button for questions. Higher upvoted questions get priority. Please keep the chat for commentary only. And for our LinkedIn Live viewers, you can post questions directly in comments, which will be relayed to us.

Now, what sets our roundtable apart is our focus on real-world applications. We bring together industry experts who share practical insights that you can implement regardless of your company size or customer engagement model.

Today, I have three outstanding leaders joining me, and I'm going to let them introduce themselves to y'all and have them talk a bit about themselves before we get started. So, let's begin with introductions in alphabetical order, as usual, with Brandon.

Brandon DeLeeuw: Awesome. Thanks, Andrew. Everyone, I'm Brandon DeLeeuw. For the past six years, I've worked in Customer Success, which, as you all know, basically means I spend my days trying to keep things personal while also scaling them without losing my sanity. And sometimes that works, sometimes it doesn't. Prior to my CS world, I worked in leadership roles at mental health and behavioral health centers. I live in beautiful Utah, as we were mentioning earlier, and I've been there my entire life. Currently, working at VisualDx, and was previously at an LMS called Bridge. I'm big on relationships, clarity, and making sure teams aren't reinventing the wheel every five minutes. I love digging into what actually helps customers feel understood versus what just looks good on a slide. Excited to be here with Michael and Cole and Andrew, who are also trying to figure out how to make personalization scalable, or at least make it look like it is. So, yeah, thanks for having me. Excited to be here.

Andrew Marks: Awesome. Thanks, Brandon. Next up is Cole, joining us from balmy Nova Scotia.

Cole Jacquard: Yeah. Thanks, Andrew. Hey, everybody. My name's Cole Jacquard. As Andrew said, I'm from Nova Scotia, Canada. My background's actually in sustainable biology, which is kind of one of my big passions. I've been in the CS/CX world for the last five years, majority of which was spent in early startup tech, based in international sustainable aquaculture, with a company named ReelData AI, where I grew Customer Success departments among other departments from scratch, managed them long-term. The last year has been more focused on professional growth and diversification for me, some of which has included digital marketing sales campaigns, as well as diversifying into B2C and B2B sales and Customer Success in solar sales, solar systems and stuff in Nova Scotia. So, that's me.

Andrew Marks: Yeah. The ReelData AI was interesting. I got exposed to that when... I'm trying to remember. You participated in, was it a bootcamp or was it the... It was the coaching cohort, right?

Cole Jacquard: Yeah, one of them.

Andrew Marks: Yeah.

Yeah, exactly.

Cole Jacquard: I was talking to Ashli, but I've done three or four of these.

Andrew Marks: Yeah, exactly. But I thought it was just interesting. We've had such a variety of people go through our training programs. People think it's all about tech. But it's interesting the different layers of tech there are out there. And we've expanded beyond just tech into non-tech domains. So, awesome. Thanks, Cole, for being here. And last but not least, Michael.

Michael Weil: Thanks. Hi, everybody. My name's Michael Weil, based in Atlanta, Georgia. I've worked in CX for a little over eight years. And I'm currently leading a team of global CSMs at Salesloft, in charge of supporting our long tail. So, I would say best part of the job, trying new things, seeing them succeed or fail, and then going back to the drawing board. I think what's interesting in our space is looking at the engagement model and being able to figure out what are those milestones and how can they be as impactful as possible. So, I think this conversation today will be really helpful in figuring out how to crack that code. So, very happy to be here, and looking forward to it.

Andrew Marks: Awesome. Thanks, Michael. And thank you all again for making the time for us. So, before we dive in, I want to challenge something that's becoming gospel in our profession. We've all been told that personalization is the holy grail of Customer Success, that every customer wants to feel special and unique, and that our job is to make them feel like they're our only account. So we've built elaborate segmentation models, invested in automation platforms, and mapped customer journeys all in pursuit of this promise of personalization at scale.

But here's my provocation for today. What if personalization at scale is actually a lie we tell ourselves? What if the phrase itself is an oxymoron, a comforting fiction that lets us feel good about what is, in reality, just more sophisticated mass communication? Think about it. When a customer receives that personalized email with their name and their company auto-populated, or, in many cases, in my case, it's not auto-populated, it just says first name, do they feel special? Because when I get the first-name email, I feel the exact opposite of special, even though I know what they're doing. Or do they see right through it?

When we route customers into segments and trigger automated journeys, are we truly personalizing or are we just categorizing humans into buckets and pretending that's the same thing? I'd argue that what we call personalization at scale often becomes the illusion of intimacy, and our customers know it. The question is, does it matter? Is the illusion enough? Or are we fooling ourselves while our customers quietly disengage? So, I'll put it bluntly. Most personalization at scale, in my opinion, is just well-disguised automation that customers see right through. Agree or disagree? And tell me why I'm wrong.

Brandon DeLeeuw: Thanks, Andrew. I'm going to jump in here real quick, get this started. Honestly, I agree that a lot of what gets marketed as personalization at scale is just automation with a cute haircut. So swapping, quote, unquote, "first name" into an email isn't necessarily personalization because customers can kind of smell that from space. But I do think that personalization is possible at scale when it's tied to intentional moments, not superficial ones. So, for example, in the past, I've implemented things like CS office hours and vertical water cooler sessions, where it allows you to... customers that could jump in and get real human experience without needing a dedicated CSM. Those moments scale because they're personal by design, not because they're pretending to be. So, you're not wrong, per se. Most attempts fall flat. But I think the concept itself isn't the problem. It boils down to the execution.

Andrew Marks: Okay. Okay. Cole, Michael, anything to add to that?

Michael Weil: Yeah. I mean, I would say maybe a little bit of a hot take, but I think you got to start somewhere. So the different haircuts and the generic personalization I almost feel like is necessary in every scenario. You don't know what you don't know yet about your customers. So when you're slicing and dicing them into different segments, you need to figure out who is engaging with your content, who isn't. And of the segments who are not engaging, how can you get more creative with that cohort? So, I think it's always worth a shot to automate and personalize at scale. Of course, we need it to be right. So I agree with Brandon in that execution is key. You can't be getting emails that say, "Hi first name." It's got to be more tactful. It's got to be better than that at a baseline. But I think that motion in itself gives you a lot of insight into who you're working with and how to get through to these customers. And then I think from there, you can pivot, you can strategize, "How do I reach more customers? How do I touch more unique accounts?"

Cole Jacquard: Totally agree with what both of you are saying. I think it needs to be flexible. It needs to be planned. And yeah, there's a lot of well-disguised automation involved in personalization at scale. But if it's done right, it doesn't really matter. As long as it's accomplishing the goals of what customers want from you, then it shouldn't really matter.

Andrew Marks: So, your comment there, as long as it's done right, I think you need to go into personalization at scale with not a set-it-and-forget-it mentality. It needs to constantly be, to what you just said, Michael, also, just constantly reviewed and fine-tuned and tweaked. "Hey, is this doing what we want it to do?" It's not just, "Hey, we're going to personalize." No, there's an effort behind that. There's an analysis behind this. And you constantly need to be fine-tuning and tweaking it. So, if personalization at scale is possible, where's the line between genuine personalization and what I'd call segment of one theater, where we're just performing intimacy rather than delivering it?

Michael Weil: I think it's a layered approach. And what we do at Salesloft is, we have an evergreen, always-on-in-the-background, proactive motion, which is, I think, Andrew, to your point, it may, I don't want to call it a ingenuine approach, because, of course, we have the best intentions all the time. I think where the layered approach comes in is you have that coverage for your customer base, and then you also have layers on top of that. "So, who's renewing this quarter and next quarter? How can we have a more aggressive approach with that cohort? How do we take a different approach by persona? How are we communicating to those contacts that we have?" So, I think a lot of the strategy from my end becomes without being overwhelming and without being spammy, because we also don't want to do that, but how do we capture those cohorts in the most intelligent way with a bunch of different avenues? Because I think it does work when you're coming at customers with different information for different reasons.

Brandon DeLeeuw: For me, I agree with everything that you said, Michael. I think that you're spot on with that. But for me, the line is whether the customer walks away feeling understood or that they walk away feeling just targeted. So, you have automation, which is great, and you need automation in order to operate at scale. There's no way to get around that. But that automation should be specific to those customers or that customer type so they're seeing what they need to see. If your personalization is basically, "We inserted your company name into a sentence," that's when it's theater, like Andrew was saying.

But genuine personalization is when you shape that experience around what the customer's trying to do, not who you as the system say that they are. So, that's why those structured human touchpoints, like you were mentioning, Michael, and the things that I mentioned earlier, like those office hours and vertical roundtable discussions and things like that, work so well, is because they're inherently personal in nature and because the customer drives those conversations. And then you can tailor some of that automation towards those things that you discover in those experiences. So, if the customer is shaping the experience, to me, that's real. If marketing automation is shaping it, that's when it becomes theater. And so, you have to be able to build off of those customer experience to develop.

Cole Jacquard: Yeah. I couldn't agree more. If you're not utilizing the data that's available to you, as Andrew said, that performance, it's an illusion of intimacy rather than actually bringing value. So, by using the data that we have available to us, you're using that true personalization to improve the customer through triggering experiences that are going on in the lifecycle, saving them time, and doing something that makes sense to them, given the moment in time that they're in and the situation they're in to bring value long term.

Andrew Marks: See, I think the problem I had wrapping my head around this as I was preparing for this is that personalization at scale is real, but I think it's often mislabeled. What most companies actually do when they say personalization at scale is one of three things. Segmented relevance, right? Grouping customers into buckets and delivering content, messaging or experiences to that bucket. Dynamic content insertion, right? So swapping a first name, company name, or product reference into templated communications, which, as we talked about during the prep call, I get too many instances on a weekly basis of, "Hey, first name." So, if you're going to do that, and I know you're going to do that, at least go through the trouble of making sure that your system works to be able to do that, because you're getting the exact opposite reaction from me when your systems screw up. And then there's the whole behavioral triggering, right? So automated outreach based on actions or lack of actions that a customer's taking.

But true personalization is the kind that makes a customer feel known, that typically requires a human being who understands context and history and nuance and can exercise judgment in the moment. And that is inherently hard to scale. So, personalization at scale is often this euphemism for smart automation with segmentation. The question isn't whether it's real. It's whether we're honest about what it is and what it can actually deliver. And I say all of this because the danger is when leaders believe they're delivering personalization and set expectations accordingly with customers, with boards, with teams, when what they're actually delivering is well-executed relevance. And that gap between intent and perception is exactly what some... There's this Deloitte research that surfaced. Brands think they're personalizing 61% of experiences, but customers only recognize 43%.

Brandon DeLeeuw: I think that when you... Part of the problem is, what you're saying, Andrew, is, there's a difference between personalization because that's very... you need a human being to do that. They have the feelings to do those things, right? You make it personal because you understand what they're going through, you understand what their goals are, and you're working toward that, which is what CS is supposed to be doing, whether we're doing it at scale or whether we're doing it with named accounts and doing things that way. A lot of companies, though, will view that and say, "Well, let's just implement some segmentation and that's going to solve that problem." And they view that as an end-

Andrew Marks: Personalization, right?

Brandon DeLeeuw: Yeah. Well, they view the segmentation as personalization, but they specifically view that as an end point instead of a starting point. So, I think a lot of people, segmentation ends up getting a bad rap because people treat it as an end instead of a starting point. If you're using segmentation correctly, you're putting customers who tend to have similar goals, behaviors, or challenges into a group that helps us design relevant experiences, whether that's through CS or whether that's through the product or whether that's through marketing or what have you. But the personalization component happens within the segment. It doesn't happen-

Andrew Marks: Within, right. Yeah, yeah.

Brandon DeLeeuw: ... because there's a segment. It happens within that with the individual customers.

Andrew Marks: Yeah. And I've read that critics say that putting customers into buckets is the opposite of personalization. It's categorization. But to your point, it's actually part of the process. So, how do you, in your worlds, now or in the past, how do you reconcile that tension? What does segmentation enable... When does segmentation enable personalization? When does it undermine it? Any specific examples you guys can think of?

Michael Weil: I think from my side, you also want to look at an engagement. So, of your customers who are highly engaged, those customers may be great candidates for self-service. We've seen that specifically at our organization. There are so many amazing tools out there that... For example, a customer can go into the iframe, they could put in their business outcomes, essentially fill out their own success plan. And then based on those business outcomes, it provides or it spits out all of these different actions of what you need to do in platform to achieve those goals.

So, I think for us, there are always going to be those customers who see the "Hi first name" or see the personalization and click out of the email and never engage or hope that it's kind of working in the background. But we love our engaged customers. We look at those customers as they're meeting us halfway. They want to see value out of this software. So we try and take advantage of that opportunity and have them help themselves, because we're all in this pooled space, in this digital space. So why not work smarter? And we've seen some great outcomes from that. Our customers love it. So, I would recommend everyone check out different tools like that because it's a pretty cool opportunity.

Brandon DeLeeuw: Well, and you can use tools like that to help even take that personalization further. So you've got a group of engaged customers and maybe they're in a specific segment. You're getting information from them. But something I mentioned earlier was what we talked about... Vertical water cooler discussions is what we called it where I worked, what I implemented. And it was the ability to take people from that specific segment and bring them into a group where we met on a regular basis. And that group could be rotating, like people, other customers could come in and out of it, but they led those discussions. And then you just had the CSM there as kind of a moderator to make sure things weren't crazy, out of hand, and people weren't saying things way out of pocket. And that kind of helps take what you were talking about, Michael, and just expanding that even further and adding more of that personalization, because now it's adding a human behind that for those engaged customers.

Cole Jacquard: Yeah-

Andrew Marks: It's like those bird-of-a-feather lunches at a conference or something like that where they'll put a topic at a table and there'll be somebody there to facilitate. But every time you go to a birds-of-a-feather topic, there's a different group of people there and you're all talking about the same topic.

Brandon DeLeeuw: Yep, exactly. And you can set those up for the different segments. So, if you've got segments specific to specific use cases, you set up those kinds of discussions for those people. And then you can take a team of three or four CSMs that are managing thousands of accounts, and each of them takes one of those a month or one of those every couple of weeks, and then it allows that personalization touchpoint, a continual personalization touchpoint for those customers so that they feel like their voice is heard. And it helps you as a product be able to pull insight out of that and be like, "This is what they're saying," and still be able to relay that information back to the product team about possible enhancements or ways that we can make things work a little bit better.

Michael Weil: Love that.

Brandon DeLeeuw: You're getting multiple things with one.

Michael Weil: Great way to build out a community, for sure.

Brandon DeLeeuw: Yeah.

Cole Jacquard: Yeah, 100%. Without that communication, like we've kind of mentioned before, nothing's set in stone. Segmentation requires constant changes and growth. Otherwise, it's not going to work. You won't be able to properly integrate people into the right segments if you're not having that constant conversation, that explore-and-discover. Segmentation to enable personalization needs to be a guide so you can use personalization as a precise trigger in those to support future pathways forward in the lifecycle. So, without that explore-and-discover, understanding the needs of each customer to integrate them into those segments, how can you use personalization, then you run into the issue of it undermining your ability to personalize those experiences within the segmentation.

Andrew Marks: And I think we are all on the same page here that even if we automate to scale, even if that automation, by definition, removes some human judgment and spontaneity, we can turn an automated touchpoint into something personal, correct?

Brandon DeLeeuw: Yeah. I mean, yeah, you can, but only if the automation is doing the heavy lifting around a personal moment, not pretending to be the moment. I don't know if that makes sense.

Andrew Marks: Right. Yeah, no, it does. But that's how it needs to be. Because, once again, personalization at scale is an oxymoron. It just doesn't sit well. And humans are still preferred. 71% of Americans still prefer human interaction over chatbots or automated processes. And 71% of shoppers on average express some level of frustration when their experience is in person, just like the frustration I express when my gardener decides to show up right in the middle of my freaking webinar every month. But it's the only day, it's the only day of the week he can fit me in. So I got to stuck it up and deal with it. Even though he's got this blower going right outside the window right now, you're not hearing that, are you? It's not too loud, is it?

Michael Weil: Can't hear a thing.

Andrew Marks: Okay. Good. Just a reminder, folks, if you have questions, please use the Q&A button at the bottom of your screen. We got one question in there, but if you got any more questions, please post them. We'll get to those here in about 10 minutes or so.

Brandon DeLeeuw: I was thinking-

Andrew Marks: All right.

Brandon DeLeeuw: Oh, sorry, Andrew. I was thinking that-

Andrew Marks: Sorry, go ahead, Brandon.

Brandon DeLeeuw: ... automation, you should be using automation to remind them of something, nudge them about something, deliver insights that they don't know they have. Recently, I was in Rochester, last week, with my company. They brought us all in, and we did a workshop. And the workshop was around the book called The Challenger Sale and The Challenger Customer. Both are really powerful insights, really dry reads, in my opinion, but really powerful insights. So, if you do read them, I definitely suggest getting together with a group of people and discussing it.

But one of the things that is in there is basically being able to surface something new that they... It's like, surfacing a problem that a customer doesn't know that they have, that eventually, you can get around to saying, "Our product solves that problem," but you don't lead with your product. And using these automations to surface a problem like that that they don't know they have also is going to drive engagements because it's going to bring them back to you and be like, "Oh my gosh, I didn't realize that that was a thing." They're going to respond back to you. And then you can insert the human-judgment component of it so that it doesn't feel like you wrote a heartfelt message from a robot. You know what I mean? If that makes sense.

Andrew Marks: Well, and I'm not sure that that's... So, this is very top of mind to me, given that we just recently released our Value-Based Selling course. It complements something like The Challenger Sale. That is very much a personalize... I mean, it's a personal thing. You can't automate that. It's all about identifying and communicating value and then delivering that message in a narrative that is going to land with the different stakeholders that make up the decision of whether or not to do that business with you.

And so, I agree that you want to be able to surface these ideas of how the customer can get more value out of doing business with you, but you need to preface that with something that I think is very personal. "This is the value that you're getting from doing business with us." That's not necessarily something that can be automated. But more importantly, even if the customer understands what that value is, and one of the biggest mistakes we see CS, people in Customer Success and account management making is they assume the customer understands the value, I mean, really understands the value. But can you make that portable so that they can tell that story themselves internally? That's not something that you're going to be able to automate. That's a very personalized thing that a human needs to do.

Cole Jacquard: Yeah. I think we were kind of lucky with ReelData, thinking about what Brandon was saying, with having that data and being able to share it and trigger personal moments with that personal touchpoint automation. It should respond to real behavior, not just generic triggers that we just assume are going to happen in the lifecycle.

We were kind of lucky with ReelData where we were able to utilize product-usage data to help trigger those things. How are people using the products? How are things going throughout the lifecycle, throughout the procedures over time of utilizing the products? And being able to identify potential issues or positive things that maybe the customer hasn't seen yet and being able to trigger that personal touchpoint without being over-touchy and over the top with our communications and being like, "Hey, we've noticed this based on the data. Let's have a quick conversation about it," or automate it in a way where they're able to update it and they have access to all that data. So they're able to utilize that data if we give them the sufficient information to share on their end and can share that with their team to keep them on page with where they are in the lifecycle with their product, but also understand the value that coincides with that triggering of information.

Andrew Marks: And that's a great segue into how you map that stuff out. So let's talk about journey mapping. Journey mapping assumes customers follow predictable paths. But real customers are messy and unpredictable. So, how do you design for personalization when the journey itself is a fiction, an average of behaviors rather than any individual's actual experience?

Cole Jacquard: Yeah. I think-

Brandon DeLeeuw: Go ahead.

Cole Jacquard: Yeah. I was just going to say, I think journey maps, they need to be treated like they're hypothesis. Like I said, everything is not stagnant and set in stone. You rarely see one of your customers doing the same thing, being in the same situation the entire lifecycle. So you need to treat it like a hypothesis. Personalization comes from how the system responds to unpredicted behaviors of the customers. So, I think personalization should be triggered by behaviors, not stages.

And one of the other things, too, is that a journey map is not just one big thing. We shouldn't be looking at it on a macro scale. It's a lot easier to look at it in micro journeys, because it's not a linear path. Nobody's ever following that pathway that you expect in a lifecycle, and you need to be prepared for that and should be around specific moments. So, are there things within onboarding that we should be focusing on? Feature discovery, drops in usage, billing issues, renewal, et cetera. Should be looking at all these different variables on a micro level so it's easier to manage, easier to review, revise, and implement rather than just expecting that it's going to be a linear pathway, which it's almost never going to be.

Michael Weil: Yeah.

Brandon DeLeeuw: I like that, Cole. A good analogy of a customer journey, a journey map is like a weather forecast. So it's like, you plan for the patterns, but you can't predict every drop of rain, so you have to be flexible for the unpredictable things. And that's where some of the things I talked about earlier, like those open office hours and that kind of a thing, because those give the opportunity for you to show up for the customer when they need you to and help in those different moments. But then focusing on renewal windows and adoption drop-offs and moments of perceived value that you would typically have a personal outreach of some kind.

Cole Jacquard: Design for chaos, not for the ideal.

Brandon DeLeeuw: Exactly.

Michael Weil: Yeah. Big +1 on that. I think one of my favorite CS leaders, who I think is on this webinar right now, Patrice Sawchuk, learned a lot about journey mapping and engagement models. And I think what I learned to be really helpful is go with the common denominator. Customers, regardless of what their background is, what's going on within the organization, they're going to love a configuration or a health check. So, if you can automate that in some way with a tool, maybe Matik or Looker or whatever it might be, that is the open door to potentially get engagement. Worst-case scenario, if they don't engage, we did our part to proactively reach out, show them usage, show them maybe where they're falling against benchmarks, where they could be improving. There's a lot of automation opportunity in there as well to just use a Gem, like a Google Gemini Gem, or there are ways to do that at scale. And we have found those activities to be extremely impactful. And they're going to elicit a pretty high reply rate. So, I think there are ways to bake those things into the journey map as well.

Andrew Marks: I've never been a huge promoter or detractor of journey maps, primarily for... A lot of the reasons based on what all of you have said, Cole in particular. Linear maps are really misleading because that's not reality. And I've recently read some interesting statistics that two-thirds of customer journey maps actually fail to drive change. It's a pretty significant chunk.

That's why we actually use this Customer Success engagement model, which is a layer deeper. That's a lot more transactional and operationally focused than a journey map. It's like a process map, amalgamated with a RACI, a communications RACI. So we just kind of mashed a communications RACI together with a process mapping, and we have this tool that we used to use. And by the way, if anybody's interested in getting a copy of that tool, I can drop a link into chat. You want that, Michael? Sure.

Michael Weil: I do.

Andrew Marks: I'll drop a shareable link. Or, Ashli, if you can grab a shareable link of the latest version of that and drop it in chat.

Ashli: Sure. Yes.

Andrew Marks: Awesome. Thank you. Okay. Oh, and by the way, we'll get to questions here in just a couple more minutes. But if you see a question on that list, looks like we got five up there now, and there's something there that jumps out at you that you want to answer first, use that thumbs-up button, because we're going to go based off of most upvotes. We're going to start at the top of the list with most upvotes. So we'll get to that in just a couple of minutes. Let's go on to a next question.

So, let's talk about customers that don't want personalization. Some research suggests that many customers actually prefer efficient transactional interactions. They don't want a relationship, they want a solution. Are we over-indexing on personalization because we value it, not because our customers do?

Cole Jacquard: Yeah. I think the big thing is just knowing your customer. I think from my experience with ReelData, there were for sure customers that they got the bare minimum in the explore-and-discover, the installation of the product, and that preliminary installation and training. But once they got the hand of what they were doing, how they were doing it, they didn't want the weekly touchpoints or the monthly touchpoints. They wanted to do what they needed to do. And when there was issues, they were going to reach out. And a lot of that had to do with persona. What's your persona within your segmentation? Are you dealing with a production manager that doesn't really want to talk to you, just wants to do what he's doing and that's it? Or are you dealing with a C-suite where they want updates all the time, they want weekly information? So, knowing who you're dealing with, which segment you're working with is important to know that. I think personalization at this point, it's relevance and reduction of effort. Yeah.

Andrew Marks: I think you got to give people a way to opt out.

Cole Jacquard: Yeah. Yeah. And that's communication, too, right?

Andrew Marks: Yeah.

Cole Jacquard: So communicating with your client. Again, I've said it a hundred times, nothing's set in stone. So understanding throughout the lifecycle that things may change. Most of our clients during the early stages were high touch. Some of them stayed high touch the entire time, all the way to full scale. Other ones after the first month, they went to medium touch, and then we barely talked to them, and we gave them updates as time went on. And that's what it was. So it's understanding their needs and working with them to ensure that you're supporting it.

Andrew Marks: Sometimes it takes a few swings at the pinata to get them to actually get it. Our LMS provider, Thinkific, who's been a great partner of ours now for almost eight years, for the first year or two, they just kept pushing this personalization thing. We use them as a content management system. We have a completely... Our learner experiences looks nothing like what Thinkific offers out of the box. So we literally are using them as a content management system. Last time I spoke to them, we are their biggest user globally. Our little company is their biggest user globally of their API. And nobody makes as many API calls as we do. So, we know their infrastructure, their product inside and out. And it took two years for me to say, "Stop with the monthly check-ins and all that. All we want from you is for you to answer the call when we call you, because if we're calling you, there's something wrong."

Cole Jacquard: Yeah. It shouldn't be the default. It should be the chosen path when we're informed by that customer's preferences.

Andrew Marks: Yeah, exactly.

Brandon DeLeeuw: That's exactly why I like models that are kind of like a choose-your-own-adventure, choose-your-own-level-of-human-engagement kind of a thing. So, you have self-serve for folks who need fast answers, want fast answers, don't want that, quote, unquote, "intimacy" or personalization. But you do have to make sure you build out a really good, strong community for that to take place, because they need someplace to self-serve from. So they need to be able to go somewhere, find the answers that they need. So, building out a community, I think, is a huge aspect of making sure that that's done. And then that also allows you to put some force, some personalization into that as well.

Andrew Marks: Yeah. All right. Final challenge, and then we'll get to questions from the audience. If you had to choose genuinely personalized experiences for your top 20% of customers or good-enough scaled engagement for 100%, which would you pick, and why? Is the pursuit of personalization at scale actually preventing us from making that hard prioritization?

Brandon DeLeeuw: So, you're saying that, so if we had to pick one, would it be 20%-

Andrew Marks: If you had to choose one, which one would you choose?

Brandon DeLeeuw: 20% deeply personal or the other option was good enough for 100%?

Andrew Marks: Good enough for 100%.

Brandon DeLeeuw: Okay. So, my thoughts here is good enough for 100%, but with selectively layered personalization for those top strategic accounts.

Andrew Marks: Well, that's not... no, no, no. That's not the rule-

Brandon DeLeeuw: You don't like my cheating answer?

Andrew Marks: The rule was you had to pick one. That's-

Michael Weil: I'm going to say good enough. I'm going to say good enough too, because I think if I know for sure that it's going to be at 100%, that's solving a good amount of the battle. And then I would imagine, with getting that outreach, you're going to get some additional insights that will allow your next move. So, I will take good enough first with the intention of being better the second go around.

Andrew Marks: Okay.

Cole Jacquard: So, I'm going to be on the opposite side of things, just to be on the opposite side of things. If I could do 100% all out, I would, and I'm still probably going to try to. But I think of the top 20%, typically your top 20%, depending on what your market is, those high-value accounts are going to be a lot more complex and require more from the provider, so from us, which cannot necessarily be accomplished if we're doing 100% good enough. And typically, that top 20% also means it's your top revenue. So if you're not able to necessarily give enough to those markets and clients, does it really matter if you're good enough for everybody when you're losing top revenue?

I also want to state that just because the top 20%, giving that genuine personalized experience, it doesn't mean you're going to completely forget the other 80%, right? You're still going to put the work in to bring the value there. But like we've talked about before, not every client's going to be high touch, right? We're going to have some tech touch, we're going to have some SMB touch, right? So we're able to support those other 80% through diversifying how we support them based on their segmentation. And it's not all going to be kind of that high-touch requirement.

Andrew Marks: Yeah, I like that. I side with Cole, thinking about our own business. I think a lot of it, it depends on what your product is, what your offering is, who your customer base is. When I think about the top 20% of our customer base, I'm thinking about customers like HP and NetApp and Red Hat and these companies that have thousands of people on our platform. My focus is on hyper-personalizing the experience for those folks because they're doing significant revenue with our organization.

Cole Jacquard: Yeah. Not every client's going to want that white-glove experience, but some of them need it, for sure. And just for some situations, good enough might not be enough.

Michael Weil: I'm not changing my answer. It was a great counter, Cole. But I would also argue that maybe the little guys are going to grow with you. So, being able to capture that loyalty up front and that trust up front, they could turn into the bigger 20%.

Cole Jacquard: Yep. I've got that written within my notes. It might be an SMB now, but it might be an enterprise logo later. So make sure you're giving them enough to be successful there. So, there's, for sure, valid points to each side, for sure.

Andrew Marks: You need to think about potential, for sure. You need to think about upside, for sure.

Brandon DeLeeuw: Then that brings us full circle. The answer is both. Whether we like it or not, the answer is both.

Andrew Marks: It is.

Brandon DeLeeuw: You got to find a way to merge the two, which was the whole point of our conversation today, right?

Andrew Marks: Well, I think hybrid is essential. Traditional Customer Success models which relied on segmenting customers into high touch, low touch, that's no longer enough. With technological advances, including digital engagement and AI and automation, that landscape shifted. And so your approach needs to as well.

So, let's get into some questions. If I can ask my guests to take a quick gander at the Q&A, I see you guys have already weighed in here. If you see a question there, by the way, that you want to jump into first, remember, hit that Answer Live button, and I will call on you. And there are no typed answers.

Let's do the refresh here. All right. Our first question comes from Danielle. Danielle, thanks for joining us today. Danielle asks, "What advice do you have for a CS org that is starting to mature its digital program for no-touch, low-touch, and high-touch segments? If segmentation is a starting point, what is next?" Brandon, look like you want to jump in on this with Danielle right out of the gate.

Brandon DeLeeuw: Yeah. Yeah. I saw this question and I was kind of excited to dive into it a little bit. So, look, if segmentation is the starting point, then your next step is going to be building the actual experiences that make those segments meaningful. So, segmentation just tells you who's in the room, and now your job is to go in and design the journey for each group. And that's not an easy task-

Andrew Marks: Do you need to design a journey for each group, or do you need to make it more into decision trees and say, "Okay, well, if this is the case, do this"? Or are you suggesting you should have this customer, this path, this process for each group?

Brandon DeLeeuw: I feel like there's a path for each group. So, when I look at segments, I'm talking about, so you have no-touch segments, low-touch segments, and high-touch customers, and then creating intentional touchpoints around milestones for each of those groups of people. Some of those can be digital, like usage-based nudges and onboarding flows and things like that, but some are human, like the office hours or the water cooler discussions we mentioned earlier, where customers can get personal experience without having to have that dedicated CSM. That allows you to be able to scale your team so that you don't have to have as many CSMs that are monitoring as many accounts at the same time.

The key is treating the digital like a product. So iterate, measure, and improve. And so, to your point, Andrew, it's going to be like you develop that journey or that map for each of those touchpoints, but then you keep yourself open to those changing, and you don't live or die by whatever you put in place. So, you're going to give those customers a choice. Not everyone needs the white-glove approach like we've been talking about, but they should feel like there's a path that fits them. So, when you design for that, personalization actually becomes scalable instead of theatrical, like we've been talking about.

Andrew Marks: Anybody else? Anybody else want to weigh in on this? Okay. Let's see. Here's our next question. Where are my questions? Thanks, Danielle. If you could hit, Brandy, if you hit the Done button there. Thanks for the question, Danielle.

Our next question comes from Cindy. Cindy asks, "Another avenue toward automation I'm seeing is using more personalization for higher-tier ACV account and more automation for lower tier. Do you agree with this strategy? And would there be any big risks to this type of scaling?" We've kind of touched on a bunch of that, but anybody have any advice or a commentary for Cindy on this? Really?

Brandon DeLeeuw: I feel like it's what we've already kind of-

Andrew Marks: Yeah, we've pretty much already covered it.

Brandon DeLeeuw: I don't know at what point in the webinar she asked the question, but I feel like we kind of covered...

Andrew Marks: Yeah, we pretty much have covered it. Okay.

Michael Weil: Are there risks? For sure. But you can-

Andrew Marks: Try shit.

Michael Weil: Yeah.

Andrew Marks: Try stuff, right?

Michael Weil: Throw things at the wall.

Andrew Marks: Try an A/B test. Try some automations with friendlies.

Brandon DeLeeuw: You can't break what's not already built, so don't be afraid to just-

Andrew Marks: Try it. Don't get sucked into the mistake of analysis paralysis where you're trying to make sure this is perfect. It's not going to be perfect going out the door. This is why you try it with friendlies. And so, if something doesn't seem right or look right, they're going to respond and say, "Hey, this isn't right." Thanks, Cindy.

Our next question comes from Jennifer. Jennifer asks, "Personalization is definitely easier with engaged customers who are telling you what they need. Can you share specific things you've done to reach your non-engaged customers outside of calls and in-product messaging?" Michael, you want to jump in on this?

Michael Weil: Yeah. I think non-engaged customers are tricky, as we've mentioned. I think there's just a natural amount of discovery that goes into figuring those out. There are some pretty cool tools out there that use AI where you can pull in things like support cases, engagement, if there's anything that is kind of like a fire drill that maybe is too difficult to parse for a rep to look into. So cutting down that manual discovery time of looking through your CRM, looking through inbound, anything that may be contributing to that lack of engagement.

I think if you can find a way to be more intelligent from a systems perspective on your non-engaged customers, it will illuminate your best next step. So, in the support-case example, if they're not engaging just because something's broken, they're not getting a ton of response from your Support team, go ahead and escalate that. That feels like an opportunity to put your arms around that customer and make them feel supported. So, highly, there's a lot of discovery that goes into it outside of calls, outside of in-product messaging, which I do think are great options. But I think those types of things help get you in the door, is figuring out what started this lack of engagement.

Brandon DeLeeuw: And are your main points of contact that you're working with, are they blockers in a sense? So sometimes you have to pull a wider lens and go around those folks. And if there's a way to tell who your top users are in your product, start reaching out to those top users and build up those champions so that you can start building a relationship that way and drive some more engagement. And then you're kind of driving engagement from the bottom-up, essentially.

Michael Weil: Also, are those contacts even at the company still? Maybe your data hierarchy sucks and that's the problem. So, yes, I think-

Andrew Marks: Well, if you've got a very short list of key stakeholders, your first step is expanding your list of stakeholders. And a stakeholder doesn't necessarily have to be somebody in the C-suite, somebody with signature authority. Influence does not follow title.

Cole Jacquard: Find your champion.

Andrew Marks: Yeah. Your champion could be an end user. Your champion could be an end user that absolutely has no signature authority, but they happen to have the ear of a senior executive because that senior executive respects that person's work and their opinion.

Brandon DeLeeuw: Well, and that end user also will champion to the other end users around them. So, the more utilization that you can prove, the more value you prove, then when it comes down time for the renewal, they're going to be a lot less likely to chop something that's getting high utilization, even if they don't personally see that value because they're not engaging with you from a stakeholder level.

Andrew Marks: Well, in a lot of cases, the stakeholders who are making the decision on whether to continue doing business with you or not, let alone expand, don't use your product, don't use your service. They reap the benefits of that usage, but they don't actually use it every day, which is why you need to have stakeholders up and down the stakeholder food chain. That's why you need to make sure that you're communicating with them in ways in which they can relate to. That's why it's important to ensure that those stakeholders understand the value that you're providing. The end-user stakeholder, the value you're providing that person, you're making their job easier so they can leave at five o'clock and go watch their kid play soccer. The value that you are providing that middle manager is going to be focused around team effectiveness and productivity. And the C-suite executive, their value is going to be focused around achieving some sort of strategic objective, some overarching corporate objective, which their comp is probably tied to in some way. Awesome. Thanks, Jennifer.

Our next question. Let's do this refresh here. Our next question comes from Virginia. Virginia asks, "What are some of the ways you have incentivized customers to move away from comfort blanket meetings that have no value but were initially part of their contract? They want them because they want them, but they really have no value." Interesting.

Brandon DeLeeuw: I'll jump in real quick on this one, at least momentarily. My last company I worked for, we had this exact experience because we had to scale back our CSM team and we're like, "Okay, how do we show up for people the same way we're showing up for people without having monthly meetings with everybody?" And it came down to, a lot of the language we use when presenting this to customers was like, "We still want to have meetings with you. We want to be able to provide value," but be honest with them and be like, "What value are you getting from this meeting?"

So, one way to do that is being honest and upfront about it, being like, I feel like, "Are we just having a meeting to have a meeting because you feel like you need to be able to get a hold of me and that this is already on the books," or like, "Here's my calendar link. You can still schedule meetings with me at any time as needed if you have something pop up, but let's schedule something on a quarterly or a six-month basis where we're touching base-"

Andrew Marks: That's dangerous. That's dangerous, man. "I'm going to give you my meeting link. You go ahead and schedule meetings whenever you want."

Brandon DeLeeuw: But the funny thing about it, though, Andrew, was it didn't translate the way you're probably thinking it would. Scarily, it could. Like, "Oh, man, I'm just going to schedule a meeting every week and every day." Actually, our workload decreased dramatically as far as meetings went. But it gave us a lot more time to be able to focus more on how to be more personal and how to solve some of the problems and help with the goals that they're trying to achieve, because we're not spending all of our time in meetings that it gave us more time to be strategic with those accounts, honestly.

Michael Weil: Yeah. We've actually taken a similar approach to Brandon in that there are some instances where my CSMs will proactively share their availability, which I think, at first thought, is a little scary. And I think the assumption is that people will take advantage of that. We found the contrary. But what it does allow us to do is capture those people who are more intent on having that one-to-one conversation, and it goes a long way. So, I think for us, it's proven to be a really big trust earner, and we've gotten great feedback about, "You guys have made yourselves available." No one really misuses it. You have to just do it in a thoughtful way. So, it's worked well. I would agree with Brandon.

Brandon DeLeeuw: And this is also where when I talked about office hours and stuff like that, this is also where we implemented CS open office hours. So, two times a day, there were CSMs that had open office hours. There's a team of CSMs. There's two of them on a call. And customers could come at any point in time, ask questions that they have, look for updates on product features, those kinds of things that you typically cover in those monthly calls when you don't really have another thing on the agenda. And you don't know what your customer's goals are because you're spending too much time in meetings with those customers.

So, it allowed us to do those things and then also implement those water cooler discussions that I was talking about where, to Michael's point, there were people that wanted those meetings, lean on those people and have them kind of lead those meetings. And then you as a CSM are just joining one meeting a month where you're talking with six customers, and you're getting a lot of insight, a lot of valuable insight about how they're using the product, what they could do differently, and they learn from each other. And I think that there's a lot of value in that.

Cole Jacquard: Yeah.

Michael Weil: Also, last thing I'll say really quick, what a great way to identify your champions, too. They really come out of the woodworks and then you can use that to inform you for the account team at large of "Here's who's-"

Andrew Marks: "This person's showing up every month to our meetings. You should reach out to them. They're going to be more receptive to this proposal that you're thinking about."

Michael Weil: That's right.

Cole Jacquard: Yeah. I think this question as a whole is a full-circle moment of this entire conversation. One of the points that Michael touched on is trust is confidence. If you do everything right up to this point, there should be confidence in your abilities. And as their confidence grows in the product, I know very specifically to the work I did with ReelData, with artificial intelligence products that we were producing, we were building out the systems for these clients to be confident in their abilities to use the products and reach out to us when they weren't confident in it. So, building that confidence through systems over time, they didn't feel like they needed that weekly touchpoint.

And that overpersonalization of weekly touchpoints or communications can increase costs, especially if your main point of contact is C-suites. Those salaries are typically a lot. So, if you're jumping on a meeting with them for an hour or 30 minutes every week, it's costly to them and costly to us and it lowers the ROI for them. So, building that confidence over time with them through SOPs, training manuals, videos, whatever, during those early stages, that explore-and-discover. And as they become confident using the products, it builds that confidence and trust. And then they feel less inclined to need those comfort blanket calls or contractual obligations that are just unnecessary at that point in the lifecycle.

Andrew Marks: Yeah. And you just end up... I mean, kind of position it as, "Hey, I don't want to waste your time. Yeah, I know we have this contractually. We can do it. But your time is valuable." So if we've done a good job at, like you said, of building up that confidence and we've done things like help them figure out how to self-serve, then "all we're trying to do is actually give you more time in your day, Mr. and Mrs. Customer." Actually take it-

Brandon DeLeeuw: Maybe, maybe...

Andrew Marks: Go ahead.

Brandon DeLeeuw: Sorry, Andrew.

Andrew Marks: No, go ahead.

Brandon DeLeeuw: I was just going to say, maybe you build that into the customer's lifecycle. Maybe you start off with weekly touchpoints or you start off-

Andrew Marks: Oh, yeah. 100%.

Brandon DeLeeuw: ... with monthly touchpoints. And then when they get to a certain point and they're self-sufficient and you've taught them everything you need to taught them as a CSM, you pull back and you're like, "Okay, let's do these a lot less frequently. And then you can have my calendar link if there's things that come up that you can't solve on your own or you can't rely on our community for."

Andrew Marks: I actually think you need to explicitly lay that out in the lifecycle-

Brandon DeLeeuw: Beginning. Yeah, at the very beginning-

Andrew Marks: Right? Right out of the gate, you got to say, "Hey, we're going to have these weekly or monthly touchpoints between now and go-live." That's how I used to do it back in the day, even before SaaS, back in the enterprise software world. "We're going to do these weekly touchpoints while we're getting through this part of the implementation. And then once we go live, we're going to move to a monthly checkpoints. And then, after three months, we're going to move to quarterlies. And then let's talk about whether we want to do them once a year, once every six months. And I'm always available to you. If you need me for anything, here's my link, here's my phone number."

But if we've done the job right and what you mentioned, Cole, and it's reflective in our training program, right? There's a reason why expansion and renewals at the end of our training program, because you got to get all this other shit right first. So if we're doing everything right and we're enabling our customers and we're helping them adopt and we're helping them understand the value that we're getting, the need for those comfort blanket meetings becomes less and less.

Brandon DeLeeuw: It also helps you distance that trap we get caught in as CSMs of like, "Oh, I'm really close with that stakeholder, so they're not going to cut us because our relationship is really good-"

Andrew Marks: Relationships-

Brandon DeLeeuw: ... which is a trap we all fall into.

Andrew Marks: 100%.

Brandon DeLeeuw: And if you're able to pull back from those weekly comfort blanket meetings, then you're going to be able to see those from a bigger lens, a wider lens, and not so focused on the one individual that you've been talking to every day.

Andrew Marks: Yeah. And by the way, just because you have a great relationship with that one individual doesn't mean you're not getting cut.

Brandon DeLeeuw: 100%.

Andrew Marks: Right? Because that person's not going to be able to go to the CFO and say, "But I like Brandon. I have a good relationship with Brandon." And CFO says, "I don't give a shit. Doesn't matter how well you like Brandon, if you can't explain to me the value that we're getting out of this, if I can't see a really transparent ROI story here between what we're investing and what we're getting out of it, I don't care how great Brandon is."

Brandon DeLeeuw: Right. It's like, "Continue your relationship with Brandon outside of work, then. We're not going to spend $200,000 a year on this product just so you can have a relationship with Brandon."

Andrew Marks: I had a friend many years ago, a friend and colleague, one of the OGs of Customer Success, who briefly took a job with the title of chief happiness officer. I just saw him last year. We were in his neighborhood visiting a college my daughter wanted to look at. And we stopped by to see him, and I gave him shit about it because I was like, "I don't care about my customer's happiness." I mean, I do, but it's not about happiness. It's about, "Are they getting a return on their investment? Are they getting value out of doing business with me?" I mean, of course, I care if they're happy or not, but in the grand scheme of things, I could care less. At the end of the day, it's, "Is my customer getting value?" Virginia, thanks for the question.

All right, we got one final question here from LinkedIn. Jeffrey, if you're still there, we're actually going to be able to get to it. Can't believe we're going to get through all the questions we had today. That's a rarity. Jeffrey from LinkedIn says, "I'm new to CS. I'm curious if office hours or vertical roundtable discussions are personalizations only or are personalization through learning community? Maybe more learning community than personalization." Semantics. I think it's a little of both, don't you?

Brandon DeLeeuw: Well, it's absolutely a little bit of both. It is personalization, but obviously, the learning community is involved, and so you're going to lean heavily on those other folks that are in those meetings. But yeah, it's still a level of personalization because you as a CSM or somebody on your CSM team is showing up, and they're there to answer the more technical questions or jump on to anything that potentially could be problematic. If they start talking negatively about certain aspects of the product, you can help correct and understand where they're really coming from. And maybe there's a way that they're operating incorrectly that you can correct in the call with everybody else there. So, opportunities there. But yeah, I think it's both.

Andrew Marks: Awesome. Michael, Cole, anything to add?

Michael Weil: +1 for me.

Cole Jacquard: Same here.

Andrew Marks: Awesome. Okay. I can't believe we're going to actually wrap up. We're going to wrap up early. We're going to wrap up on time, actually early.

So, here's what I hope you all take away from today. Stop chasing personalization at scale. Start chasing relevance with humanity. Scale your system, scale your data, scale your efficiency, but never scale away from the thing that makes customers stay, the feeling that someone on the other side actually gives a damn.

And with that, we've reached the end of today's session. I want to thank our guests for sharing their valuable insights and experiences. Your contributions make these discussions truly meaningful for our community. To our audience, thank you for your active participation. Share your thoughts about today's session on LinkedIn by tagging me, our guests, or SuccessHACKER. We always love to hear your takeaways. Check back on to the website as well as our email announcements about our next roundtable in January. Once again, new format. We've already got the first three topics laid out. I'm just not sure what the order is. Do we have an order yet, Ashli? Do you know what the order is of those?

Ashli: Yes. One sec.

Andrew Marks: And by the way, Ashli is the person that really runs the show here. So, thank you, Ashli, for everything you do.

Ashli: We're starting off with customer health scores and predictive analytics.

Andrew Marks: What date is that, the first one, that we decided on?

Ashli: January 21st.

Andrew Marks: January. And we're going to be doing them third week of the month moving forward? Is that what we decided?

Ashli: Yes, correct.

Andrew Marks: Awesome. So, look for that. Look for the new format. And then, finally, let me leave you with this. Great CS leaders know that they don't have all the answers, but they know where to find them, and that's why we created this series. And we hope that you subscribe to the next series. Have a great rest of your day and month. Happy Holidays, everybody. I hope you have an awesome holiday season and new year. And I'll see you in 2026, actually. And next week, Kristi Faltorusso, once again, will be standing in for me at the CS Mastermind. She's always a lot of fun to host the program. So, check her out next week. And she will be subbing in for me regularly next year. So, once again, Happy New Year, Happy Holidays. See you next year.

Every subscription-based business faces churn. It’s an inevitable part of the customer lifecycle. While Customer Success strategies focus on preventing it, few invest in a tactical next step that can turn the tide: winning customers back. In this guide to churned customers, we’ll cover exactly that.

Churned customers represent a very unique segment. They’re people who already saw enough value in your solution to buy once, who understand your product, and who likely still have the same business challenges you help solve. Compared to net-new prospects, winbacks are well-poised to close faster, at a lower acquisition cost, and can even stay longer the second time around. Studies show that on average, when “winback campaigns” are initiated, a quarter of customers return, and that nearly half of these customers generate more revenue the second time around. But to earn their business back, you need to understand and address the root cause of their churn and demonstrate new value.

In this guide to churned customers, we’ll explore how Customer Success teams can turn churn from a dead end into a second chance. You’ll learn how to identify signals of readiness, craft outreach that rebuilds trust, and operationalize a scalable winback program that delivers measurable ROI.

This article will discuss:

• What is a churned customer, and why do they churn?

• Are winback attempts worth it?

• How should you segment churned customers for targeted winbacks?

• What channels and plays are most effective for winbacks?

What Is a Churned Customer, and Why Do They Churn?

Every CSM is familiar with customer churn. But to kick off this guide to churned customers (and winning them back), we first need to understand why customers leave in the first place.

To start: what actually counts as churn? There are different types of churn, such as when:

• A customer terminates the contract in its entirety (account closed). 

• A customer spends less than before. This includes downgrades, seat reductions, and product/module cancellations.

• The account lapses due to factors like payment failure or insufficient funds, also known as involuntary churn. Research shows this category accounts for up to a quarter of customer churn. 
  

Next, what are the reasons customers actually churn? There are five typical root causes that CSMs encounter:

1. Value Gap (Outcomes Not Realized)

Symptoms: Low adoption in core use cases, champion disengagement, “we’re not seeing ROI.”

Underlying drivers: Misaligned success plans, weak onboarding (results in 23% average customer churn), limited stakeholder buy-in.

2. Product Fit

Symptoms: Integration issues, high workaround usage, “missing X feature that we could really benefit from.”

Underlying drivers: Use case mismatch, integration blockers, performance/reliability issues.

3. Price, Terms, and Packaging

Symptoms: “Too expensive,” the customer wants features that are in a different tier (but are unwilling to pay for it).

Underlying drivers: Misalignment between perceived value and cost, plan doesn’t fit usage patterns. 

4. Service and Relationship Breakdown

Symptoms: Slow/frequent support ticket, reactive CSM cadence, sentiment turns negative. 

Underlying drivers: Team turnover, unmanaged escalations, lack of celebrated success milestones.

5. External or Administrative Factors

Symptoms: Budget changes, mergers/acquisitions, executive hires.

Underlying drivers: Org changes, vendor rationalization, budget shrinkage. 

Winning back lost customers starts by understanding why churn happened in the first place, so you can identify the root cause.

Are Winback Attempts Worth It?

You might be thinking: “A lost customer is a lost customer, why should I focus my efforts on winning them back?”

While it’s true that many churned customers are a “lost cause,” in many cases, winback attempts are worth the effort. 

What’s the upside?

• Faster, cheaper revenue. Returning customers already know your product and implementation. This means they can have shorter cycles and lower CAC than net-new customers.

• Higher second-life retention. When the root cause of their original churn is fixed, returning customers can stay longer and expand faster than first-time buyers.

• Competitive advantage. If they left you for a rival who disappointed them, your timing and proof of change can turn their new pain into urgency to buy.

But of course, in some cases, a winback is unlikely and therefore not worth pursuing. This includes scenarios where: 

• The root cause of churn is unchanged: If you’re still missing a client’s must-have feature, or the pricing doesn’t work for them.

• Structurally unprofitable: Sometimes, a client simply isn’t worth it. If their support load is too high, their customizations are too extreme, or their service costs are bloated, it can cut into your gross margins.

• Toxic or noncompliant fit: High-risk use cases, legal exposure, or repeated nonpayment can indicate that a churn is better left as-is.

Not sure if a churned customer is worth pursuing? You can create a simple green/yellow/red rubric to determine which churns you should chase:

• Green (proceed): We’ve addressed the churn reason, the value story is provable, champion still employed, there’s a new application for our solution.

• Yellow (test): Partial fix exists, willingness signals are present.

• Red (hold): No fix, no signals, economics don’t work. Revisit after a material change (such as a new feature release or pricing update).

How Should You Segment Churned Customers for Targeted Winbacks?

Next up in our guide to churned customers: a detailed customer segmentation plan which helps you execute targeted, successful winbacks. There are five different segmentation buckets that should influence your winback approach:

1. By Reason for Churn

Understanding why a customer churned is one of the most critical segmentation criteria. Common reasons might include:

• Pricing issues: These customers may have found your service too expensive or may have chosen a competitor with more favorable pricing.

• Product fit or features: Some customers might have left because they didn't feel your product met their needs or lacked specific features.

• Poor customer support: Customers who experienced frustration with customer support might need assurance that their concerns will be addressed.

• Lack of engagement: Customers who never fully engaged with your product might need additional onboarding or education to see the value.

• Competitor switch: Customers who churned in favor of a competitor may need to be convinced that your product offers unique benefits they can’t get elsewhere.

By segmenting based on reason for churn, you can tailor your messaging to address specific pain points directly. For example, your pricing options versus a more costly competitor, or the deployment of certain features. 

2. By Usage or Engagement Level

Churned customers can also be segmented based on how frequently or intensively they used your product or service:

• Heavy users: These customers likely found value in your offering but perhaps experienced an issue that led them to leave. Offering them an exclusive feature or a personalized offer may help win them back.

• Light users: Customers who barely used your product may have been overwhelmed, confused, or simply didn’t see the value. You could approach them with re-engagement campaigns that highlight the full potential of your service or offer a guided tour to refresh their understanding.

• Active trialists: For customers who churned after a short trial, it might be worthwhile to analyze whether they had enough time to see the full value. Offering a second chance with an extended trial could be a great re-engagement tactic.

Segmenting based on usage will give you insight into how familiar the customer is with your product and whether they may require a simpler, more hands-on approach or a more advanced strategy to win them back.

3. By Time of Churn

Timing is also an important factor in segmentation. For example:

• Recent churns (1–3 months ago): These customers are still likely to remember the experience they had with your product (for better or for worse). A quick follow-up with a personalized offer or a survey could reveal opportunities for immediate winbacks.

• Long-term churns (6+ months): Customers who have been gone for a longer time might need more education or a stronger incentive to return. A "we miss you" campaign, a new feature announcement, or a special deal could reignite their interest. Or if they’ve gone to a competitor, you can check in with them to see how it is going and tailor your message to address any pain points they’re still experiencing. 

Timing also plays a role in how much the competitive landscape has changed since the customer churned. If your product has significantly improved, make sure to highlight those changes in your messaging.

4. By Customer Lifetime Value (CLTV)

Not all customers are created equal when it comes to their value to your business. Segmenting churned customers by their Customer Lifetime Value (CLTV) helps you prioritize efforts:

• High-value customers: These are customers who have historically generated significant revenue for your business. They are worth investing more time and resources into a winback strategy. Offering them high-touch, personalized engagement is key.

• Low-value customers: While important, these customers may not warrant the same level of effort. A more automated or scaled approach, like an email campaign, may be more appropriate.

Segmenting by CLTV lets you focus on customers most likely to return and deliver substantial future value, while ensuring you don’t neglect those with growth potential.

5. By Customer Demographics

Segmenting by demographics can provide a deeper understanding of your churned customers’ characteristics and help you tailor your approach:

• Industry (for B2B): If you’re in the B2B space, customers from particular industries might experience unique challenges. Segment them accordingly and tailor your outreach to align with their specific needs or pain points. For example, perhaps their market went through a downturn (which is why they churned), but has since recovered,

• Customer Size: Smaller customers might churn due to budget constraints, while larger clients might have been dissatisfied with the product’s scalability. Offering customized pricing or a premium solution could be effective for each group.

This segmentation helps in crafting messaging and offers that are highly relevant to the customer’s context, which increases the likelihood of a successful winback.

What Channels and Plays are Most Effective for Winbacks?

When it comes to winning back churned customers, choosing the right channels and plays is just as important as segmentation. The key to re-engaging churned customers is delivering the right message, at the right time, through the right medium. Each customer may prefer different communication methods, and your approach should align with their behavior and preferences. 

Here’s a breakdown of the most effective channels and plays for customer winbacks:

1. Email Campaigns (Personalized and Automated)

Email remains one of the most effective channels for customer winbacks. However, a generic email blast won’t cut it. Best practices include: 

• Personalized messaging: Use customer data to personalize the subject line, body content, and call-to-action. Mention specific actions they took before churning, or highlight product changes that may be relevant to their needs.

• Re-engagement sequences: Create a Digital Customer Success drip campaign that gradually reintroduces value, starting with a simple reminder of what they enjoyed about your product and ending with an exclusive offer or incentive.

• Automated triggers: Set up automated winback email flows based on the timing of the churn. For instance, if a customer churned 30 days ago, they could receive a “we miss you” email. After 60 days, you might offer a special promotion or a demo of new features.
  

2. Customer Success Manager Outreach (High-touch, Personalized)

For high-value churned customers, or customers who are well-poised for a winback, a personalized outreach from a CSM can make all the difference. This approach is particularly effective when the churn was due to factors like poor customer support, unmet needs, or feature gaps. Best practices include:

• Personal calls: A phone call from a CSM shows that you’re genuinely invested in the customer’s experience. Use this opportunity to listen to their concerns, provide solutions, and offer exclusive benefits to return.

• Customer feedback sessions: Engage churned customers by inviting them to share their experiences in a feedback session. Not only does this show you care, but it can also reveal insights for improving your product.

• Consultative approach: Offer solutions tailored to the customer’s specific challenges, guiding them using a consultative approach. For instance, if they left due to a missing feature, you could demo that feature or offer a solution they didn’t know existed.
  
  

3. Webinars or Demos: Educational and Engaging

For customers who left because they didn’t see the value in your product or misunderstood how it could solve their problems, hosting a webinar or offering a product demo can be a highly effective play. Best practices include:

• Exclusive invitations: Offer churned customers exclusive access to a webinar where you can demonstrate new features, share success stories, and engage directly with them.

• On-demand demos: Provide easy access to on-demand demo videos that allow customers to explore the product at their own pace.
  
  

Turn Churn into a Second Chance

If this guide to churned customers leaves you with anything, let it be this: churn isn’t the end of the story, it’s a diagnostic tool. When you treat it that way, you can learn and address reasons for churn. Then, winback becomes a disciplined, high-ROI motion that can bring back customers—faster, cheaper, and for a longer time.

Frequently Asked Questions About Winning Back Churned Customers

What is a churned customer?

A churned customer is when a customer leaves your business or downgrades their service. They might close their account, spend less than before, or their account might lapse due to payment failure.

Are customer winback attempts worth it?

Oftentimes, yes. In many cases, churned customers are not a “lost cause,” and winning them back can be cost-effective, lead to longer second-life retention, and give you a competitive edge. But in some cases, a winback is unlikely, such as if the root cause of their churn is unchanged or the partnership is unprofitable. 

How do I segment churned customers for targeted outreach?

By five different buckets: reason for churn, usage or engagement level, time of churn, Customer Lifetime Value, and customer demographics. This segmentation helps you craft messaging, tactics, and offers that increase the chance of a successful winback.

What channels are most effective for winbacks?

Email campaigns (personalized and automated), Customer Success Manager outreach, and webinars/demos allow you to reach customers where they are, re-educate them on value, and provide a white-glove experience where it counts. 

In today’s market, new customer acquisition is challenging, competition is fierce, and expectations are high. Against this backdrop, customer onboarding has grown from a checklist item to a mission-critical process, which plays a central role in determining whether businesses thrive or struggle. But it’s not enough to have “any old” onboarding process in place: it needs to be a well-designed onboarding that accelerates time to value, builds confidence, and establishes trust.

If you’re wondering how to improve customer onboarding processes in your business, it makes sense. This small window of opportunity is where new customers first decide if they’re achieving their goals with your product, and sets the tone for their entire journey. 

For Customer Success functions, customer onboarding is not just an operational task; it’s a core revenue-driving strategy. This article explores practical ways to improve your onboarding process so you can consistently and methodically drive higher client retention.

This article will discuss:

• Why is onboarding critical to customer retention?

• Steps for radically improving customer onboarding.
  
  

Why Is Onboarding Critical to Customer Retention?

To understand how to improve onboarding, Customer Success teams first need to understand why it’s so essential for customer retention. Onboarding is more than just a speedy product tutorial: it’s the moment when customers start forming long-term impressions about whether your solution will truly deliver on its promises. If customers don’t start to “click” with your product, they’ll begin questioning their investment, and the likelihood of churn increases dramatically.

Several factors make onboarding vital for retention:

• It sets the first impression: Customers expect the buying experience to flow seamlessly into their first interactions with your product. A smooth, confident onboarding signals that your team and solution are prepared to guide them toward success. One survey found that more than 80% of businesses say their onboarding strategy is a key driver of value.

• It accelerates (or delays) time to value: Excellent onboarding helps customers understand how to use your product better, faster. This can lead to higher customer satisfaction and reduce the risk of early churn.

• It shapes customer confidence: Early wins reassure customers they’ve chosen the right solution. On the other hand, if onboarding feels unhelpful or overwhelming, they might question their choice. Nearly three-quarters of customers say they will switch solutions if onboarding is complicated. 

• It directly impacts renewals & expansions: In the customer’s mind, renewals are often decided long before a contract end date. If they don’t integrate your product into their workflows, they’re less likely to consider expansion or renewals down the road. 
  

Onboarding is much more than a step in the customer journey; it actually is the foundation for retention.

Steps for Radically Improving Customer Onboarding

Figuring out how to improve customer onboarding processes requires focusing on the moments that matter most to new customers. The best onboarding programs expertly balance efficiency with personalization, ensuring that every new customer feels guided towards early wins, while also building confidence in the long-term value of your solution.

With that in mind, here are proven strategies Customer Success functions can follow to not only improve onboarding, but ensure it directly correlates to better customer retention.

1. Accelerate Time to Value

For onboarding to lead to retention, customers need to start seeing value quickly. This concept, known as time to value (TTV), is the period between when a customer first signs on and when they achieve their first meaningful outcome with your product or service. Typically, the shorter the TTV, the higher the likelihood of long-term adoption. 

Think about things from the customer’s perspective: they’ve invested time, budget, and energy in choosing your solution. They want to know if they made the right choice, and quickly. If they don’t see results early, frustration builds, confidence wanes, and churn risk skyrockets.

Here’s how to accelerate time to value:

• Design for quick wins: Identify the simplest, most impactful outcomes a new customer can achieve within the first days or weeks. 

• Segment your onboarding paths: Different customer segments require different onboarding journeys. SMBs may benefit from streamlined self-service onboarding, while enterprise clients may require live workshops to reach their first milestones.

• Highlight progress: Track and celebrate early usage metrics, such as first workflow created or first campaign launched, to show tangible progress.
  
  

2. Personalize & Proactively Support

One of the most common onboarding mistakes is treating all customers the same. A generic training program rarely inspires confidence or boosts customer engagement. Also, proactivity can help avoid problems during onboarding and improve the overall experience. That’s why personalization and proactive support are both essential to onboarding.

With personalization, remember every customer brings a unique set of goals, workflows, and challenges to the table. A healthcare organization adopting your platform will have very different success criteria than a retail startup. Likewise, executives want to see ROI metrics, while end-users care about improving day-to-day workflows. To personalize onboarding:

• Segment your customers: Design onboarding tracks based on company size, industry, or use case. These customer segments allow you to meet customers where they are.

• Deliver role-specific guidance: Provide tailored enablement for executives, admins, and frontline users so each group quickly sees value in their context and doesn’t waste efforts wading through content that doesn’t apply to their roles.

• Use discovery to inform training: During the onboarding kickoff, clarify the customer’s top goals and needs. Then, align onboarding around those outcomes.

Next, when it comes to proactive support, keep in mind that waiting for customers to raise issues is risky. They may silently disengage and then it’s difficult to get back on track. Instead, CSMs should proactively reach out during onboarding to check progress, address concerns, and celebrate early wins. Frequent touchpoints build trust and reduce the risk that small challenges will snowball into bigger frustrations. 

3. Treat Onboarding as a Retention Engine

As we’ve discussed, onboarding is the foundation of retention. How you design, measure, and evolve this phase directly impacts whether customers renew, expand, or churn.

Here’s how you can ensure onboarding is a catalyst for retention:

• Gather continuous feedback (and iterate): Use surveys, interviews, or in-app prompts to understand how customers are experiencing onboarding. Act quickly on needs and pain points to improve your process.

• Track meaningful metrics: Measure onboarding success by tracking metrics such as engagement during the first 30 days or product usage milestones.

• Strive to create advocates: A well-executed onboarding process should not only produce retained clients but also create vocal brand advocates. The goal is not just to educate customers, but to set them on a path for long-term success and renewal.
  
  

Driving Retention Through Better Onboarding

Customer retention doesn’t happen by chance: it’s built and nurtured from a customer’s earliest days with your company. And onboarding is the critical moment where trust is established, value is proven, and momentum is created. The best Customer Success teams figure out how to improve customer onboarding by earning, measuring, and improving. By accelerating time to value, personalizing support, taking a proactive approach, and ultimately treating onboarding as a retention engine, you ensure every new customer is set on a clear path toward renewal and advocacy. 

Frequently Asked Questions About Improving Customer Onboarding

Why is customer onboarding important for retention?

Onboarding is where customers form their first real impressions of your product and company. A strong onboarding program accelerates time to value, builds confidence, and sets the foundation for long-term loyalty and renewals. 

How can I reduce churn with better onboarding?

You can reduce churn by:

• Delivering quick wins that prove value.

• Tailoring onboarding to the customer’s industry and role.

• Proactively engaging to solve small issues before they grow.

• Iterating on feedback, ensuring the process improves over time.
  
  

How can I improve my customer onboarding process?

Three steps can help you improve your onboarding process:

• Accelerate time to value, which is the period between when a customer first signs on and when they achieve their first meaningful outcome with your product or service.

• Personalize onboarding so customers feel like your solution was built for their needs. Also, proactively address issues and concerns to prevent challenges from occurring and snowballing. 

• Treat onboarding as a retention engine by gathering feedback, tracking metrics, and iterating your process.

CS Mastermind #79 Transcript: Prioritizing High-Impact Customer Success Activities

With increasing demands, growing books of business, and limited time, Customer Success Managers must become masters at prioritization. Not every task holds equal weight, and spending time on the right activities is essential to drive real value for both customers and the business. By focusing on high-impact actions like strategic conversations, success planning, and value realization, CSMs can make a measurable difference in customer outcomes and long-term retention.

This webinar helps CSMs get clarity on where to direct their energy for the greatest return, providing a focused mindset and a smarter approach to managing time and impact.

In this CS Mastermind session, our panelists discussed:

• Activities that have the biggest long-term impact

• Balancing urgent customer needs with proactive, strategic work

• Managing “busy work” that doesn’t contribute to outcomes but still needs to get done

• Frameworks or tools used to prioritize tasks and customers

• The role account segmentation plays in activity prioritization

• Measuring the impact of activities on customer outcomes

This webcast featured:

• Chad Horenfeldt, VP of Customer Success at Siena AI

• Cinthia Silva, Enterprise Customer Success at Global Relay

• Patrice Sawchuk, Customer Success Leader

Top Takeaways:  

1. Outcome-focused engagement creates more value than activity-based metrics. Rather than tracking the number of meetings held, Customer Success teams can measure progress toward specific customer outcomes and business goals. When CSMs structure their interactions around achieving measurable results, they naturally prioritize strategic conversations that drive retention and expansion over routine check-ins that take time but don't move the needle. 

2. Strategic conversations require thoughtful preparation and clear objectives. Before every customer interaction, CSMs should identify what they want to accomplish and prepare questions that uncover business challenges tied to customer outcomes. This preparation ensures that every moment spent with customers contributes to high-impact activities. 

3. Setting and maintaining boundaries enables CSMs to focus on strategic work. Establishing clear expectations around response times and communication channels creates space for the proactive, value-driving activities that truly impact customer success. CSMs can safeguard time for strategic thinking and maintain strong customer relationships by leveraging tools such as time blocking and scheduled email sends. This allows them to effectively prioritize activities that drive measurable business results.

4. Customer segmentation empowers CSMs to maximize their impact. By focusing premium attention on strategic accounts while implementing efficient digital touchpoints for others, CSMs ensure their limited time gets invested in the highest-impact activities. 

5. Business reviews succeed when they prioritize forward-thinking strategy. The most effective customer engagements dedicate minimal time to looking back and instead focus on co-creating plans for future success tied to specific business outcomes. By framing traditional quarterly reviews as strategic checkpoints, CSMs can significantly increase their impact. 

6. Cross-functional alignment amplifies the effectiveness of CS activities. Building strong internal relationships with Product, Support, and Sales teams enables CSMs to set realistic customer expectations, communicate feature requests with compelling business cases, and resolve issues efficiently. These partnerships free CSMs from becoming the catch-all for every customer need, allowing them to focus their expertise on the strategic, revenue-driving activities that only Customer Success can deliver.

Session Replay

Session Transcript

NOTE: The following transcript has been edited for clarity and content where necessary to improve readability.

Andrew Marks: Welcome, everyone. I'm Andrew Marks, co-founder of SuccessHACKER and our SuccessCOACHING training program. Thank you for joining our monthly CS Mastermind webcast, where we bring together professionals from across the customer experience ecosystem, from Customer Success Managers to Support specialists and everyone in between. Today's session on prioritizing high-impact CS activities is brought to you by SuccessCOACHING, where we've helped more than 40,000 customer-facing professionals from almost a hundred countries, got to be careful how I say that, develop the skills they need to excel. Whether you are in Customer Success Support or any customer facing role, you can find the right program for your learning style.

A couple of quick notes. November is Career Development month, so we're offering a hundred dollars off on our new Value-Based Selling curriculum. Ashli's dropped more details into chat. Also, we'd love to hear what's top of mind for all of you these days. Please, help us pick next year's webcast topics or let us know if you'd be interested in being a panelist. Ashley's also dropped a link into chat to join our survey. Your input is important to us. You can find all the details of any of our offerings on our website, successcoaching.co.

Now, CS Mastermind's all about real world expertise. No theoretical frameworks or abstract concepts here. We dive deep into practical advice and actionable insights that you can apply immediately in your role. As I mentioned today, we're exploring how to identify the most effective activities that Customer Success Managers should focus on for maximum impact. But some quick housekeeping items before we begin. We're recording this session and we'll share the replay next week. Please, use the Q&A button for questions. The most upvoted ones will get priority during our discussion. LinkedIn Live viewers, feel free to post your questions directly in the comments. For smooth sailing, please keep the chat window for commentary only.

Now, I'm excited to introduce our fantastic group of returning panelists, who will be sharing their insights with us today. As usual, I'll let them introduce themselves to you all in alphabetical order, and therefore, we'll start with Chad.

Chad Horenfeldt: All right. Thank you so much, Andrew. My name's Chad Horenfeldt. I'm the VP of Customer Success at Sienna AI. Sienna is this empathic AI agent, and we have created this intellectual layer in AI for commerce. What we essentially do is just help respond to customer tickets for B2C e-commerce, so it's a very busy time, and then, we're expanding beyond that. I've been in Customer Success for many years. My team is currently at the seed stage. It's very early stage startup, but I've worked in companies of all different sizes. And, I've recently wrote the book the Strategic Customer Success Manager. So happy to be here, and yeah, looking forward to the discussion.

Andrew Marks: Awesome. Thanks, Chad. Once again, congrats on the book.

Chad Horenfeldt: Thank you.

Andrew Marks: Onto Cynthia.

Cinthia Silva: Yes. Hey there. Cinthia Silva here. I've held client-facing roles on both sides of the customer journey in finance, tech and FinTech. I went from sitting on trading desks for banks in Seattle and New York to pivoting to tech, and I've worked at companies such as IHS Markit, Refinitiv, NASDAQ, and now, as an Account Director at Global Relay, which is an e-comms surveillance and archiving solution. I'm a big believer in communities, which is why I'm active in and hold board member roles at CX Exchange, Latinos in Success, CS Middle East. This year, I started hosting live events in New York City for the local Customer Success community, and I'll be doing the same moving into next year, because these interactions, I think, are super valuable for everybody. Thanks for having me here. Looking forward to this conversation.

Andrew Marks: Awesome. Thanks, Cinthia. Like I mentioned, I am sorry that I missed the CS week in New York this year. As I told John, I really want to make it next year, and potentially, I'm going to be on a panel or something like that. Definitely interested in Support ing the East Coast, and I got a whole slate of Northeasters here. We're going to finish things up with Patrice.

Patrice Sawchuk: Hi, everybody. Patrice Sawchuk, really excited for today's session. I've been building and leading Customer Success functions, gosh, for the better part of 15, 20 years. I've had the pleasure of leading Global Success functions for some really incredible software companies throughout my career. After taking some time off to be with my family and while I search for my next CS leadership opportunity, I've started my own consulting practice, because topics just like the one we're about to discuss today are prevalent in our space. I've been helping companies strategize for their response to our ever-changing market, stand up digital and scale functions and create AI strategies. Again, happy to be here today, and really looking forward to contributing to this session.

Andrew Marks: Awesome. Thanks, Patrice. Patrice hails from one of my favorite cities in the Northeast that I have a lot of family ties to out in Boston with my father actually being born just outside Boston and Amesbury, Massachusetts.

Patrice Sawchuk: Awesome.

Andrew Marks: Awesome. All right. Thanks all once again for making the time. Let's get this going. Today, we're going to challenge some sacred cows in Customer Success. Let me start with a bold statement. Most CSMs are wasting at least 40% of their time on activities that do not meaningfully impact customer outcomes or retention, and the data backs this up. Research shows that the average worker is productive, get this, for only 2 hours and 53 minutes each day. Not even 3 hours of your 8-hour workday. Employees spend 50.1% of their workday on tasks of little to no value. On top of that, my gardener's right outside my window again on top with his blower. On top of that, employees are interrupted about, there's my interruption, 60 times per day on average, and it takes approximately 25 minutes to recover from each interruption. That's a productivity nightmare. We're not just busy, we're busy doing the wrong things.

Here's the kicker. Many of those activities are things we've been told are essential to being a good CSM. We've built this mythology in Customer Success that good CSMs are available 24/7, that we respond to every customer message within minutes, that we attend every internal meeting we're invited to, that we meticulously log every interaction in the CRM, and that we treat every customer in our book of business with equal attention and care. We wear our responsiveness and our busyness like a badge of honor. Let's talk about that culture of busyness that's plaguing our profession. A recent study found that 58% of American workers say they're so busy with daily tasks that they lack time to consider anything but what's on their to-do list for today. Despite all this activity, only 20% of the average working day is spent on activities that actually matter, that actually move the needle. We're confusing motion with progress.

But I'm going to argue that this approach is not only unsustainable, it's actually bad for your customers. The top challenge Customer Success leaders identified for 2024 was delivering value to customers with scaling Customer Success ranking as the second biggest challenge. Here's a reality check. Nearly 70% of CS teams still don't have formal enablement programs. That means the majority of CSMs are figuring this out on their own without any sort of structured Support or training. While you're busy being busy, you're not doing the strategic proactive work that actually drives long-term value. You're not having the tough conversations about adoption, you're not building success plans that align to business outcomes, you're not identifying risks before they become churn events. The truth is, not all customers deserve the same level of your attention. Not all requests are actually urgent. Not every meeting is required for you to attend. And some of the best practices that we've been taught are just keeping us on a hamster wheel.

The CSMs who have the most impact aren't the ones doing the most. They're the ones doing the right things and having the courage to say no to everything else. I talk about this all the time in our training. You create your own time management nightmare. Today, we're going to have an honest conversation about what really matters. What's just theater and how to break free from the busy trap. I've got three CS leaders here who aren't afraid to challenge conventional wisdom and tell you what actually works, not just what sounds good in a LinkedIn post. So let's get uncomfortable.

Let me put this out there. Most of what we've been taught about being a responsive and customer-centric CSM actually trains customers to be overly dependent and prevents them from becoming self-sufficient. First question, do you agree or disagree? What's one commonly accepted Customer Success activity that you think is overrated or actively counterproductive?

Patrice Sawchuk: Absolutely agree. I would love to jump in. I think probably the most overused thing is our reoccurring check-in meetings with no agenda and no clear objective or success criteria. I think that happens all over the board, and I think that's an activity-based model versus an outcome-based model, and that just is busy. It's busy, it's not driving outcomes.

Cinthia Silva: Yeah, I agree with that. And also, I think to build on that, it's one of those things, even if a meeting, a recurring meeting, was useful, sooner or later these meetings become stale and it's time to really assess those as a CSM. Again, if there's no agenda, then there's no point to the meeting, and I think it's okay to check in with your customer in that respect, I hate that word, check-in, but in that respect to say, "Hey, listen, do we need to look at this frequency?" And as a leader, you need to be helping the CSMs look at that as well and not make that a metric of like, "Oh, you're not meeting with them 2.5 times a month or whatever."

Andrew Marks: I've actively pushed back against leaders who had that as a metric they're tracking.

Chad Horenfeldt: Yeah. I think, on that one, the better metric is, first of all, I'd say an effective meeting, what's a type of meeting that is going to actually drive impact? But more so, one would be a lagging indicator like NRR, and then, the second one would be more on perhaps some sort of value-driven adoption metric or are you capturing outcomes? Just to add to this, and maybe this is, I don't know, it's controversial, but the traditional thing we teach CSMs is to collect product feedback. I would argue that if you just collect product feedback and you just do it without a filter, that's another activity. It's a bit a waste and also sets wrong expectations, because you turn into this waiter type of persona, where you just sort of accept whatever the customer's telling you in terms of, "Oh, you should build this really awesome, amazing cup holder that would be so cool to have."

But what is that actually driving, and what impact is that going to have? A lot of times, the response is, "You know what? That's really interesting. All right. Let me submit that to our product team and we will get back to you soon and see if we can get that on the roadmap," rather than qualifying that and really trying to understand, "Okay, you've told me that your outcome is to achieve this. It could be to gain more efficiency or to unlock additional automation that could lead to additional revenue. How is this particular thing that you've suggested going to achieve that? How does that compare to this other feature that we've already discussed that's on our roadmap?" Anyway, so that's just something that-

Andrew Marks: That's a great point, because what you're doing in that instance is you're elevating it from a tactical conversation to a strategic conversation. The only way that we are going to deliver value at the level at which a customer says that, "I can't operate without this partner of mine," is elevating the conversation from tactical to strategic. Here's how what we are doing for you is going to impact your bottom line.

Chad Horenfeldt: Yeah. It's kind of going back to what Cinthia is saying. A lot of times, we go into these conversations, and the idea of a cadence or a check-in meeting, the idea of it is a good one, because you're having a touch with the customer and you can uncover potential issues, you could help them solution, items they're trying to work through. But a lot of times, CSMs are so jammed because they have so many of these cadence meetings that they're not adequately prepared for them, and then, they just don't necessarily hit on the mark that you want them to.

Andrew Marks: Well, like Patrice ... I'm sorry. Go ahead, Patrice.

Patrice Sawchuk: I was just going to say, I think, unfortunately, this behavior is often driven by the way CSMs are measured in their organization and so-

Andrew Marks: That's a drive behavior, anybody?

Patrice Sawchuk: Yeah.

Andrew Marks: Right? Yeah.

Patrice Sawchuk: I would encourage everybody today to think about how are you measured, and is it number of meetings, and are you encouraged to have these static reoccurring check-in meetings, and maybe either challenging that, if you're so brave to do that, or take a look at your own calendar and figure out if you are required to check off the box from an activity perspective. How can you make sure those meetings are purpose-driven and outcome-driven and their purpose is to drive larger corporate level objectives or metrics that your company is tracking?

Andrew Marks: Right, or is their purpose just to keep you busy? I think we do them, and sometimes managers throw them out there and tie comp to it because they're afraid, "If we don't, we'll lose touch with our customers."

Patrice Sawchuk: Yes.

Andrew Marks: All right. But think about it. If nothing's changed since last month, you're just creating noise.

Patrice Sawchuk: Yes.

Andrew Marks: I've seen CSMs spend hours preparing decks for these meetings and customers barely engage. Cinthia, you mentioned the importance of effectiveness. What's counterproductive is that it trains customers to wait for you to reach out to them rather than coming to you when they actually need help.

Patrice Sawchuk: Yeah.

Chad Horenfeldt: Yeah. It's another thing along those points, and it's been talked about a lot. Like I mentioned in my book around the ineffectiveness of QBRs, it's another type of engagement. The idea of the QBR is great, but I think that we get too wrapped up in the slides, in what we think should be produced for that rather than what the customer wants and what will actually drive a valuable conversation, and so just like you're saying like preparing the slides. I think that there's a lot of efficiencies now. We're actually experimenting with Gamma.

We just bought licenses for our team, and we've uploaded a template, our PowerPoint template, and we're starting to use Gamma for everything now. Just very simple proposals that we want to send to a client. Like here's a 60-day plan to get things back on track. Literally, taking that plan, putting it into Gamma, and it creates this beautiful presentation. The focus is not the slides. The focus is the communication, what you're trying to achieve. And similarly, with business reviews, really want to focus on the conversation, the discussion and what the customer's trying to get to rather than try to get through your slides.

Patrice Sawchuk: Yeah.

Cinthia Silva: Yeah. Chad, I'm really glad you brought up QBRs too, because everyone loves to hate QBRs, but it's only because a lot of times it's us just talking at the customer. We're quoting the stats that we want to quote to them. We're talking about our roadmap and the things that we want to show them to potentially upsell them, et cetera, and we're not engaging them at all. I think, unfortunately, when those situations happen, which happen often, it's not a great exchange. But that's why, like the QBR and EBR, a BR or whatever, should be interactive. It shouldn't be this big surprise and unveiling, it should be like, "Here's the deck we put together. What do you want to see?" Add some slides that you want to talk about about your business and the things, so that we can customize it. I don't think there's enough of that that goes on.

Patrice Sawchuk: No one wants to get on a call and be read the news. I don't want to sit there and listen to you read the news to me. In order to plan forward, you got to look back a little, and so there has to be some, "Here are the things we did," but you need to be co-creating these QBRs together. What does the customer want to be doing? How can you strategically plan together for your partnership?

Andrew Marks: You also need to be reminding them of the value that they're getting.

Patrice Sawchuk: Yep, absolutely.

Andrew Marks: It's not the tactical value, the strategic value. Once again, strategic.

Chad Horenfeldt: Yeah. In my book, I actually, it's funny. I throw out the word review because I think of review as, I don't know if everyone remembers, you did a book review as a kid and you'd stand up in front of the class and everybody would just tune out and it'd be so boring. Nobody likes a book review. In fact, like what you're trying to do is to come out of the meeting with a plan. At least a few, two or three things that you want to accomplish, and so, it's more forward-thinking. To your point, Andrew, really 20% should be a look back, and I've kind of renamed it strategic checkpoint, which came out of a previous company I was in, someone on my team came up with that. And then, we just loved the term. We actually saw a 40% increase in decision-maker, like executive stakeholders that would attend, because we would frame it up like a board meeting.

If you ever attended a board meeting, board meeting is essentially just what you were saying, Patrice, where I think you said where you give the information ahead of time, there's a pre-read and then there's discussion questions that come out of that pre-read, or kind of a free discussion. And then, you come in and everyone's read the materials and there's a few slides, the rest are in the appendix, and there's discussion questions like an open discussion. That way, the focus is more on, "Okay, what do we do next? There's a bit of a look back, but what do we do next?"

Andrew Marks: There's an anchor, right? Okay, here's what we did up until now. Now, let's talk about, okay, what the next, because you're right, the board meetings, they're very much 20%. What did we do last quarter? Okay, where are we going to go now with what we've done, based off what we've done?

Chad Horenfeldt: Here's a problem that we've seen in this data that you send we have to focus on. I didn't know about that. This is really interesting. Let's talk more about that. That really engages people. When you're on a meeting, and video goes off, people are on mute, you know there's a problem. You've lost your stakeholders there, and you probably won't get them back the next time you want to schedule a meeting with them. The way you have to think about it is, with everyone being so busy, there's so many vendors that companies are working with, that's your one chance. I like to call it like your World Series, your World Cup, your Stanley Cup, whatever it is. That's the game, the moment, that you really have to shine, and you have to be prepared and it has to be engaging. It comes down to your preparation, but it also comes down to think, Cinthia, you had mentioned, just not a rudimentary discussion, but coming with prepared questions that are really going to get your customers to think.

Maybe some pieces of information that you know about their business. You've done a little bit of research, you can use AI obviously to do that. You come back and say, "Okay. This is what I've heard. This is what I've seen." Just curious, knowing that these are your priorities or your outcomes we've discussed, have you thought about this as something that's important? Just getting into-

Andrew Marks: You constantly need to be asking the why. Why are you doing business with us? Why is this important? Has anything changed? Business reviews, I found some really interesting statistics about business reviews, because this is where things really get interesting. Recent research revealed that 88% of buyers state that suppliers aren't demonstrating enough evidence of value and innovation in business reviews, and 60% believe suppliers are getting by on delivering the bare minimum. It's not landing folks. You're going to spend your time doing this stuff, it needs to land. Eighty-two percent of buyers have canceled a contract, because they felt their supplier didn't deliver enough value and innovation. This is why we came up with the Value-Based Selling course, and the foundation of this is all about making sure that the customer understands the value, and that's demonstrated in things like business reviews. Okay.

Chad Horenfeldt: But they don't have to be business reviews.

Andrew Marks: They don't. I like the way you positioned it. Business review is the term. Business review was hijacked back from, in the on-prem days, we used to refer to quarterly business reviews, but they were very much looking forward reviews. Do you remember those?

Chad Horenfeldt: Right.

Andrew Marks: It would be an internal thing, where we would get together, it would be post-Sales and Sales getting together on a quarterly basis, "Okay, here's our plan." We looked at it as, "Oh, here's our review for the business that we're going to get this next quarter."

Chad Horenfeldt: But it also doesn't have to be a meeting either.

Andrew Marks: No.

Chad Horenfeldt: Showing that value, this is where, going back to the original question, the overuse thing. This is where the more creativity and creative approaches and Customer Success are starting to emerge more and more.

Cinthia Silva: Chad, I'm really glad you put that up, because I think that makes me, because you touched on AI before, and I know we're going to talk about it later too. We know that Customer Success is typically under-resourced. Andrew, you talked about it in your intro, right? And so, we get this what I call the Sales leftovers. But one of the sneaky ways, if you don't have any tools to upskill yourself or get, maybe some strategic points is, if you have. If you record a meeting, because it's easy to get those notetakers in your meetings, you could take that and do it yourself into ChatGPT or something and say, "Hey, what are some of the strategic points I missed?" You know what I mean? To make yourself better, to teach yourself. And then also, based on this customer's business, this is their role, this is a conversation we had. What things can I think about going forward?

I know there's tools that are available that supposedly do that, but a lot of CSMs aren't getting those tools. But that's a way that you can actually upscale yourself, and then, be more strategic and ask better questions. Because Chad, you're absolutely right, the minute you start really boring your audience, they don't come back, especially the key stakeholders, because they're very, very busy.

Patrice Sawchuk: Yep.

Andrew Marks: A hundred percent. These people are people who need to look at things, look at their business a mile wide and an inch deep. They do not have time to go down freaking rat holes with you. What's interesting, we touched on communication a few times there. Recent research shows that knowledge workers invest 88% of their entire work week into communication. Managing emails, attending meetings, team chat apps. Here's the kicker, they're losing 19 hours a week just on written communication alone, 19 hours. That's almost half the standard work week.

Building on all of this, let's talk about availability. There's this expectation that CSM should be constantly accessible. But doesn't that just learned helplessness in our customers? What boundaries have you set around availability? How do you train your customers to respect them without damaging the relationship? Something that I am constantly reminding my folks to do is, if it's not a critical response, do you really need to respond to that customer 15 minutes after they sent you an email? If you do it every once in a while, that's okay, but you're doing it all the time and you're conditioning them to a 15-minute response when our SLA is clearly documented in one business day.

Chad Horenfeldt: Yeah. I think, for the most part, I don't know any customer that really knows an SLA. It's just not there, so I don't think it's top of mind. Maybe if they email you or message you a lot, then, you remind them. It is interesting. One thing we do here that's a bit unique is that, I'd say over 90% of our customers interact with us through Slack. A lot of people that joined our CS organization like, "Wait a minute, what? Slack. I don't know. That's a little scary." What's really good about it is that our Support is driven through the same mechanism. Each of our clients have their own Slack channel. What's cool about it is that every message that comes in from our customers goes into our help desk, and so our Support team is kind of like the backup.

Everything is documented, and so, the customers know that, and so they know, and they know that nothing's going to get lost. I think that's one thing. Whatever thing you have, just reassuring your customer that, "Hey, these messages will get back, and there will be some sort of response." The other thing that we have is, we use Sienna, so we use our own technology as a first response, so it's an AI response, and it will handle all basic questions and advanced questions now, and so that we can actually respond and deflect things right away. That's an interesting, and I'd say, newer type of approach. But I think, ultimately, it's setting the right expectations and sometimes resetting them and not feeling that you need to respond right away.

Andrew Marks: Yeah. It has to be ... and you may know that response. All you got to do is set it up to send later. Every email program these days has a send later function. It's that simple. You can respond to it, just send it later. Send it in 12 hours, send it tomorrow same time. You're creating your own problem. Ninety percent of your customers engage via Slack. I think, for where you're at in the evolution of your company that works for you, I think that you get too big, I don't see how that's sustainable personally. If that works for you-

Chad Horenfeldt: [inaudible] discussion, but just because it's in Slack doesn't mean you're responding right away. And also, because we have Sienna and we call it a her, Sienna responds. We have it set up, there's thinking time, we call it. It's not automatic, so it doesn't seem too fake, but she responds within a few minutes. She typically has a really great response. And then, if not, she routes it automatically. It's all about setting those expectations, so I think you've done well. But to other people in the point making notes in the Slack channel or in our own chat here, yeah, listen. You have to, has to be properly administered for it to work well.

Andrew Marks: Yeah.

Patrice Sawchuk: Yeah. I think everyone should strive to create self-sufficiency in their customers. I think the world is changing too. You're always going to have those customers that want to pick up the phone and call you. I want to be self-sufficient. I don't want to have to wait for you to respond or get off a call. I think, to Chad's point, setting really clear expectations, holding the boundary is super important. Finding a talk track that's authentic to you, that makes you comfortable to say, "As I shared with you before, here are my roles and responsibilities. Here's how you can find this information."

I think the other piece is, if you are measuring your worth or your value to how responsive you are to your customers, it's back to that activity tracking. Your intellectual knowledge is capital there, and so, I think it's super-important to make sure that you're not measuring your value to your customers by being their Google. It's just not sustainable.

Cinthia Silva: That's a good point too, because I think it's like the difference between Customer Success and customer service 2.0. Because a lot of times those questions that customers that email you that you can answer quickly are probably customer service questions. And so, you have to discipline yourself, as well as the CSM, to say, "I'm going to either respond to the customer, or I'm going to forward this to our service desk, copy them, and then I'm going to say, 'Hey, listen, you need to send these types of requests to service desk, so that we can log them, and we have a process in place. Feel free to copy me, if you want me to be aware.'" Those are part of boundary setting, and again, making your time freed up for better conversations. This just brings me to your calendar in general. Like I really do. I'm a huge believer in blocking time, time-blocking for deep work, because if you just turn off the notifications and you can do, even just an hour a day, it's amazing.

If you took an hour to look at some of your accounts, even just one account, if it's a critical account, you can get more done and make more of an impact within that space than answering a bunch of customer service type questions throughout the day.

Chad Horenfeldt: Yeah. One thing that you just said, Cinthia, that's really, really important, or it made me think about it, is that the question sometimes to ask yourself is, "Well, why are customers coming to you? Why aren't they going to Support?" A lot of times, when people are coming to you, you're like, "Well, I have to train the customer to go to Support." But I remember Kristi Faultorusso, so she says something really important. Sometimes you have to lean into this and try and find out, ask the customer, "Well, why are you going to the CSM?" And a lot of the times is that it could be the response time of Support. It could be that maybe they had a bad experience with Support. This is where going back and thinking about how you can better leverage AI, because to everyone's point, it's about getting to the answer and getting to the solution.

This is where if you can provide a better automated response or just improving your Support, then this also then saves the CSM from getting those particular questions. And then, on the flip side, talking about prioritization, as a CSM, it's very easy to gravitate towards the thing that's burning the most or the warmest or whatever, the house that's burning down, because it's easy. It's like, "Oh, that's burning. I'm going to go get that. I want to go focus on that." But I'd say what's harder is that when you get up in the morning and you ask yourself, you probably do a little bit of analysis looking at your accounts and your priorities and say, "What's the one thing that's going to help me the most today to drive towards my goals?", and thinking about what that is, and then setting time in your calendar and making sure you have time allotted to that.

It could be maybe reviewing your accounts, looking at the data that you have and saying, "Okay, this particular client, I haven't talked to in a while. Let me just take a quick review and see what's going on there based on health score. There's maybe a potential issue." Or, "I have to prepare for this particular meeting. This is what I'm going to do, because there's an upsell opportunity and they've told me that they really want to look at this." It's just being very, I don't know, just taking that first step and rather than letting work come at you, because work will come at you.

The last thing is that, sometimes it's okay to let things fall. Customers, maybe they're escalating something to you that is also with Support, let them go and let Support do their job. That's a hard thing for CSM, because they feel they're compelled to respond, but let other groups do their stuff. You need to do what you need to do. If it escalates, then the odd time will escalate. But it's better to do that than to be running around and not adhering to those things that are the most important that are going to drive the most impact for you and the company.

Andrew Marks: I love what Patrice said about not being their Google and Cinthia, your point about reinforcing proper workflow to set boundaries and what Chad just said about understanding why customers are reaching out. I think it really, really highlights how we've confused responsiveness with effectiveness. And the point that Chad just made, the importance of resetting expectations, stop being compelled to respond. Once again, this is about you. You control your calendar, you control your schedule, your busyness that's driving you crazy is, 90% of that's a product of you letting that busyness get in there.

But this is where it gets interesting. When we do set boundaries and we step back from being constantly available, we're told to rely on our data and our health scores to tell us where to focus our limited time. That's the promise. Let the data guide your prioritization. But I want to challenge the assumption with some data. According to a recent TSIA report, only 30% of companies actually adjust their health scores based on changing business conditions. They said it and they forget it. They think it's a freaking Ronco oven.

What that means, Cinthia knows what I'm talking, she's watched late night TV before. That means 70% of companies might be making decisions based on metrics that are outdated or no longer relevant to their current reality, which is why we always talk about how important it is to constantly be reviewing and updating your health score data. Here's my hot take. We spend enormous amounts of time on health scores and dashboards, but how often do those metrics actually predict churn better than just having a real conversation with your customer? Are we over-engineering prioritization when gut instinct and relationship intelligence might be more reliable?

Patrice Sawchuk: I think it's a both scenario. I think, in this day and age, especially with the pressure to scale and depending on your company, you could have a super long tail business, it is really difficult, I think, to operate a modern success organization without health scoring capability. As part of my consulting practice, that would be one of the first recommendations I would make. However, to your point, Andrew, it absolutely needs to be current, dynamic, valid, whether you've got an incredible analytics team in-house and you build it in-house, or there are amazing vendors out there that do a great job with health scoring. I've worked with many of them. And so, I will say, the other piece of it is you have to then, with your data team, go back and check the model. Look at your churn data and look at your health score predictability, and see where it fell short.

The goal is to get as predictive as possible. I think, to answer your underlying question, Andrew, it does not remove the need for the human element. That's our job. That's our function. We know our customers. We're not a data model. And so, I think the force multiplier here is combining those two things. You have a dynamic, accurate predictive, health scoring model, and then, you have CSMs who know their customers, and they need to use their judgment when to jump into a customer and why based on what they're seeing and they know of their book.

Andrew Marks: Well, I want to add one more thing to that. I'm sorry, Cinthia. I want to add one more thing to what Patrice just said, that the additional force multiplier is not just the CSM showing up, but showing up with the right message, with the right data, with the right narrative.

Patrice Sawchuk: Yes.

Andrew Marks: Once again, back to what we led with, make sure that the conversations that you are having are strategic, not tactical, because that's just a waste of everybody's time. Sorry, Cinthia. Go on.

Cinthia Silva: Yeah, no worries, no worries. Here's my challenge with health scores. They're absolutely necessary, but what we do often is we treat health scores in the same way that we treat engagement strategies with customers. If we're not doing a segmentation analysis and looking at how to engage with and/or the health scores, they're wildly different. One common metric for the health score is tickets. How many tickets are they putting in? If an enterprise customer with 10,000 employees puts in 50 tickets in a month, that might be low. But if like a mid-market puts in 50 month, that's a red flag.

Andrew Marks: That's a problem, right.

Cinthia Silva: If you've got health scores that are exactly the same, no good.

Patrice Sawchuk: You got to normalize it for ... Cohorting, I think, is really powerful there.

Andrew Marks: You need to be smart about it. Chad, anything to add?

Chad Horenfeldt: No. I think that what I've seen with health scorers is they can be very effective when they're tied to value. If you see a customer that's underperforming, and to Cinthia's point, it's best to have it from different segments, different products. But when you can tie it to value and you see, "Okay, this customer is underperforming," it can help you prioritize where you need to focus on. The problem is that you can't become overly reliant on it, especially for higher segment like enterprise type customers, because a lot of that is based on the characters, the stakeholders that are there. You could have something that looks green and a new stakeholder comes in or a stakeholder you didn't know about, because you didn't map it properly comes in, so say, "We're just doing everything differently here," and then you can find yourself on the street. So that's-

Andrew Marks: Watermelon. We call that the watermelon account, green on the outside, red on the inside. You have no freaking clue, unless you are sitting in the meeting room hearing the decisions being made.

Chad Horenfeldt: Well, even if you're in the room, the challenge that, and this is something that I talk about a lot in the book, is that a lot of the CSMs are not necessarily trained on how to conduct themselves when they're in the room with those key stakeholders. What are the questions that you need to ask? How do you actually get to the underlying issues? Going back to the original question I was asked, one of the things that we do that, I'd say, that we're being asked to do, and it's not necessarily that impactful, is that we're asked to talk about the new features. "Oh, we've got these great new features that were launched." That's great, and that's important to do that. It's fun, it's exciting, especially if they're really cool. We have have some new features, but if they're not tied to their business or what their-

Andrew Marks: Exactly, if they're not relevant, what's the point? You're just wasting, yeah.

Chad Horenfeldt: Yeah. You're just wasting time. It's a similar thing when you're coming into a meeting with a stakeholder and you have no idea how to conduct yourself, how to ask questions that are going to be impactful, how to influence this person in the right direction. Then, you're just throwing your CSMs into the lion's den and hoping for the best. And then, the customer churns and you're like, "Well, you met with them. What happened? What's going on there?" Health score looks green. You've been giving these great pulse checks, and then, meanwhile, they're still churning.

Andrew Marks: Yeah, exactly.

Cinthia Silva: Chad, I really love that, because you touched on two things that always resonate with me. Due diligence before it calls with your customers and discovery, the power of discovery. That's not limited just to Sales, because I think that's where everybody buckets discovery. That should happen across the customer journey, and that's exactly what you're talking about, in terms of the differentiation. These very light questions, "Everything good? Good." No, you need to dig a little deeper. And if you've done due diligence, you know what they've done in the past, you know maybe a little bit about their business, and you're asking deeper questions and maybe uncomfortable questions.

Andrew Marks: That literally, identifying communicating value and having good discovery meetings is literally, it's like a quarter of the Value-Based Selling. It is the cornerstone, literal cornerstone, of driving retention and expansion. Whether you're using health scores, you're using gut instinct, you're using a combination, we're constantly told that we need to be proactive, we need to schedule regular check-ins, sending in those check-in emails, the QBRs, because that's what good CSMs do. But what's interesting is that, and I mentioned this before, research found that 88% of buyers say suppliers aren't demonstrating enough value and innovation in those business reviews.

You know what it is? They're not tying the feature function tactical shit to something strategic. Why should I care about this? 88% and 60% believe their suppliers are just getting by on delivering the bare minimum. What's even more concerning though is that 82% of buyers have canceled a contract, because they felt the supplier didn't deliver enough value. They may have delivered the value. They may have delivered the value that they promised, but we've done a shitty job connecting that, for helping them understand the value that they're getting and then making that value transportable, creating a narrative around that value, so that they can explain the value that they're getting to other people in the organization, because guess what, folks, decisions aren't made by a single person, unless you're in the S of the SMB. Unless you are the S of the SMB, a decision is being made by a cohort of individuals, including somebody in finance, who at the end of the day, just wants to understand what the ROI is.

And if you have not articulated a strong ROI case and you haven't been able to create a story that they can then tell others within the organization, you will be part of the 82%.

Chad Horenfeldt: Yeah. It's a good point. A couple of things. One is showing there's different ways to show value. A lot of the times, your customers, and especially if you're working with your day-to-day, they won't even have thought about value and communicating that up. This gives you an opportunity to actually create the narrative. One of the things that we've done is, we've created an ROI calculator. It takes in a few inputs. It's pretty simple, the first iteration, and if they want to deeper, we can do a deeper one. But just by doing a very simple, showing them the math and showing them, "Well, here's how much money you're saving," it's really impactful. They're like, "Oh, I didn't really think about that." And then they're like, "Okay, well, how are you going to use this? How can we use this to communicate to the right people who should receive this?"

That's a good question to ask. Who would feel left out if we didn't send this to them? It's another way of phrasing it, and so that way, you can unlock additional stakeholders that you may not have known about. That's one thing. And just one other thing, going back to that original question of things that we shouldn't do. A lot of times, our leaders will say, "Save every account at any cost." I think that one of the worst metrics, this is probably controversial, is a logo retention metric. The reason is that, especially depending on the stage. If you're late stage and you've got all enterprise clients, logo retention is really important. You can't lose the click.

But I would say that GRR net retention like a dollar amount is more important, because there are some clients that it's not worth spending your time on. You're not going to save them, they're not the right fit, and sometimes, they were the right fit and they've changed and they're no longer the right fit. That's where it's really hard for the CSM. Going back to handling Support tickets and responding, you have this hero mentality and you have to, shit, take off the superhero costume. You have to take that off. You are not the superhero. You have an organization, you have a particular goal, and that's part of the problem. All right. Andrew is okay.

Andrew Marks: I'm not the superhero.

Chad Horenfeldt: This is going the direction of this webinar.

Andrew Marks: I love that. Yeah, it's true. It did. Yeah, you nailed it.

Chad Horenfeldt: Took me a long time to actually not feel as guilty when I lost a client, as a leader as well.

Andrew Marks: It's okay, yeah.

Chad Horenfeldt: It is okay at times.

Patrice Sawchuk: And if we're working on nurturing and growing our customers who really are a good fit for us, then that revenue will offset. Because you will spend more money trying to retain unhappy customer or a customer that is a bad fit than if you were to pivot and work on nurturing and growing your existing customers that are a good fit.

Chad Horenfeldt: Yes.

Andrew Marks: Awesome. You know what? It's already, wow, it's already 10 to noon. I knew this is going to be a good conversation. We only got through half the questions that we had developed. We've got about a half dozen questions in the Q&A. I think what we're going to do is we're going to turn to those now. If you have questions that you would like to serve up to the panelists, please add those to the Q&A, or use that little thumbs up button to upvote questions that you want want to get answered. Just a reminder, we do go until a quarter past the hour, so we will answer as many questions as we can get through over the next 25 minutes. I'm going to ask that my guests take a look at those questions. I see Patrice has already volunteered to jump in on the first one, but if there's something, Cinthia, Chad, that jumps out at you that you've got something to jump in on first, go ahead and hit that answer live button, and I will call on you first.

Let's get started with M. Gwynn. M. Gwynn, thanks for joining us, appreciate the question. M. Gwynn asks, "What would you all suggest is a better metric to track than the number of meetings with customers?" This is just, I love this, Patrice, because I think you are the one that brought up right out of the gate there's a difference between activity-based and outcome-based.

Patrice Sawchuk: Yeah. I think meeting, or maybe I'll take the word meeting out of it. Engaging with your customer is table stakes. As a CS leader, I expect you are engaging with your book. And now, depending on segmentation and the tools that you have, that looks a little different, whether it's meetings and digital and all that type of stuff. I'm not looking to measure how many meetings or what types of meetings you had, because that's my expectation. That's what you're doing. You're engaging with your customers. I think if you are building these engagement moments intentionally around driving outcomes and ideally customer outcomes. Customer wants to do x, y, and Z, and your solution is the vehicle to do those things, they're solving business problems. The more strategic a business problem you can get, the more strategic a stakeholder you'll get. If you measure those outcomes and you track the data that's measuring those outcomes, like capture the outcomes somewhere.

Customer wants to do X, Y, and Z, so I think the first thing I've done in someplace is, you're required to document and capture customer outcomes, part of success planning or however you want to go about it. Everybody needs some outcomes captured. And then, the indicators that your meetings are effective or your engagement with your customers are effective and that you're meeting with them enough, is the measurement of the customer achieving those outcomes. Also, are your customers staying with us? Are they growing with us? Are they using product? Is their sentiment high? All those traditional Customer Success metrics will skew in your favor if when you meet with them, your meetings are structured and intentional around outcomes and value.

Andrew Marks: I love that. I think you need to go that, and then you got to take that next step. "Okay, well, what does the customer doing X, Y and Z mean?" If you're talking to them at the user level, then what does that mean to the middle management? If you're talking to them at the middle management level, and this is where, as I've used the term before, black swans, from Never Split the Difference, Chris Voss, you discover those black swans. Once you understand, well, what does that mean at the middle management layer, because that's going to give me a window into strategically how is what we do having an effect on the organization. And then, you want entry into the C-suite and you can start building a narrative around, "Here's how what we're doing over here is helping you CXO achieve your desired outcome, which is implementing this strategy and what you're likely being comped on.

Patrice Sawchuk: Absolutely.

Cinthia Silva: I love that you brought that about the different stakeholders, Andrew, because-

Andrew Marks: Different levels.

Cinthia Silva: ... you're absolutely right. The hidden thing about the C-suite is they want to know what they don't know. Any sort of market intelligence that you can bring them, that is what they're going to value versus what others are going to value. If you talk to them about like, "Hey, we got this new feature," they're like, they'll just send you down to somebody like a user or some middle manager. Here's a sneaky metric that I would also measure, and I think it's a tricky one. It's measuring the amount of super users, advocates, and champions you have at each account, particularly in the enterprise space. Because we know, if we have one champion and they leave, you are so vulnerable to churn. I think, if you start measuring those, and we know that those are different levels, a super user versus a C-suite advocate versus a champion that might be middle of the road or senior, but the more you have, and I think it's relevant across all types of businesses, small to large, but it's most relevant in mid to large size companies.

Andrew Marks: I think you got to do a quantity and quality thing.

Cinthia Silva: Yes, yes.

Chad Horenfeldt: Yeah. We're starting to do that now at the more enterprise. It's more of not just the quantity, although quantity is important, like making sure you have, especially the larger accounts, are you covered where someone leaves that you still have further connection? But the quality of the relationship is important as well. How strong is the relationship? Is it a new person? Set that person to a weak relationship unless somebody knows them. We always look for common connections, and then, we look to connect with that particular person. But what I would say, there's a question, I think it's from Mary, and she asked, how do you handle situations where you're consistently restating boundaries and resetting expectations with clients?

I definitely think that the different levels of stakeholders is important. For example, a lot of the times what I find is that, we instruct customers to follow certain process when submitting, let's say, Support -related issues. A lot of times, those aren't necessarily followed. The first thing I would do is try and ask, "Well, why? Why is that not being followed? What's the question? What are the challenges?" Also, just re-emphasizing the why, like why we need you to follow this process? If you follow this process, we'll be more efficient. We'll make sure that we process your particular requests and that we understand there's not as much back and forth. And so, you'll get what you need and then, we'll be able to deliver on what it is that you want.

But sometimes that stuff doesn't work. Getting back to the decision maker and talking to the decision maker about benchmarks and trends and inside information, a lot of times, they want to understand, like how is their team operating? If you've built a trusted relationship with them, then you can almost operate on a level where you can give them guidance and say, "This organization is running fairly effectively, but here's what I've seen these other organizations in terms of how they're structured or how they operate and how we work really well with other organizations." Unfortunately, we're not necessarily seeing that level of cooperation and here's kind of what we need from you, how does that sound? You have to be very delicate. Again, you have to build trust, but these are some ways that you can get around those situations. But definitely, not easy, Mary, so it's part of our job, unfortunately.

Andrew Marks: Patrice, I think you had some, I want to weigh on on Mary's question as well. Let me restate it. Any recommendations for how to handle situations, where you're constantly restating boundaries and resetting expectations with clients?

Patrice Sawchuk: Yeah. I think anytime you can reinforce in writing, that helps too. If it's in a call, it can get misinterpreted or forgotten. I think, anytime you can reinforce expectations in writing, any way you can tie it to the way it benefits them. A talk tack I've used in the past is, "Hey, so that you don't have to wait for me to get back to you," or, "If I'm out of the office and I can't get back to you," or, "If this is time-sensitive, this is the process we have in place." And then, just make sure they're educated on what the alternatives are, like are there office hours? Is there any knowledge base? Is there a chatbot? Play up why that benefits them, why they might get the answer faster. I think, just be super consistent. As soon as you waiver from that, it's like training an animal or raising children or consistent theme.

Andrew Marks: It's all about training.

Patrice Sawchuk: You've got to change the behavior, yeah.

Andrew Marks: You've got to reiterate it constantly. The only way you're going to change, and you know what? They're not necessarily, they're not going to follow through the first time. You need to expect that and just keep reminding them.

Cinthia Silva: Well, another thing about managing expectations, because I do think it's tough sometimes. It seems like every massive problem is funneled to the CSM, because it's the everything department.

Andrew Marks: Exactly, the everything department.

Cinthia Silva: Yeah, a hundred percent. One of the ways that I think that is another maybe sneaky way or around. Like maybe ways to set better expectations is by maybe developing better internal partnerships. Because earlier, Chad, you brought up rightly so about customers talking about certain feature requests, and then you're trying to get more strategic about why they'd want that. But we know feature requests often die on the vine, because our product team has their own objectives. If it's a good idea, it might not work. If you can set better expectations, sometimes that's just by having a better relationship with the product. First of all, never promise a good customer anything, because that's the only thing they remember. But if you have a great relationship with product marketing, Sales and whoever other it's customer service, then you can actually say, "Realistically, what should I say in these circumstances?" Or, "This is what's happened. What, realistically, should I ... Tell me just the truth. Let's work together. How can we work towards something like this?"

Building those internal relationships, because what I've seen in so many companies, is these fiefdoms, where in certain instances, people, teams not only just work in Sales, but sometimes they actively work against each other, which is insanity as the customer loses. As the CSM, if you build those relationships, you can set better expectations.

Andrew Marks: Well, and also, beyond that, and with product in particular, I also find that Customer Success Managers aren't telling the right story in the right way to product. Are you just asking for a feature or are you explaining the business case? Are you explaining what a percentage of customers are affected? The most important thing is attaching a revenue number to it. There's this potential revenue at risk for this potential upside. Because at the end of the day, I don't care if they got a freaking fiefdom and they're doing everything in a vacuum. At the end of the day, when the C-suite at your company learns that product is avoiding something that is either high revenue risk or high revenue potential, money cures all ills. Make sure that you're communicating with product in the right way. That's how you're going to be effective working with them. Patrice, can you hit the done button on both of those for me?

Patrice Sawchuk: Yup, will do.

Andrew Marks: Let's move on to the next question here. As we just pass the top of the hour, just a reminder, we're going to keep going here for another few minutes, so if you can stick around with us. Okay. We got somebody from LinkedIn live. Marcelo asks, "When having monthly and annual subscribers, how would you prioritize or schedule check-ins accordingly?" By the way, you use the term check-in internally, great. If you actually use the term check-in when you're communicating with your customers, stop now. Okay. "What three questions should I ask myself in order to strategically automate check-ins with my customers?"

Chad Horenfeldt: Yeah. The first thing is I'd like to know what's the monthly recurring revenue, so how much is this customer paying you? Because if they're only paying you a little bit amount, I wouldn't check in with them at all, because it's not worth it. You don't have time. But let's assume that there are, out of a significant amount and you're asking, "Who should I check in with?" I would look at, depending on the life cycle, like where they are in the life cycle, let's say they're earlier on in the life cycle and maybe they haven't hit, you have certain thresholds, things that you want to see happen in those journeys. I would have something set up to look for those customers who haven't achieved whatever success metrics you want to see, and then, go in to help those particular customers.

More advanced systems you may have collected, what their outcomes are, and you can tie whatever their outcomes are to whatever they're actually achieving. And if there's a gap there, then that's kind of where you want to jump in. You may have regular elements in your customer journey, where at this point of the journey that maybe we do audits for our customers. We go in a 10-point inspection and we're trying to automate that audit. And then, we can go and say, "Hey, we've set up this audit for you. We would like to go through this with you, our results. How does that sound?", and you make it easy for them. Or, you send them a video and you see how engaged they are in that video. There's just different things that you can do, but you want to think through the journey, think through the stage of the journey, start small, try a few different things, experiment, and go from there and build on that. That's what I would recommend.

Andrew Marks: Account segmentation is supposed to help us prioritize, but I'd argue that most companies don't have the courage to actually execute on it. Is segmentation just a theory that doesn't work in practice, or are we implementing it wrong? Because if it's hard to execute and we're all stretched thin, the solution we're being sold is automation and digital Customer Success. That promise is compelling. Automate the routine stuff, free up CS time for high-value, strategic work. AI and automation is going to save us all. I think they're destined to help.

Cinthia Silva: Yeah, but as a CSM, you can actually segment your own book of business. Because sometimes, the way these book of businesses are done is it doesn't make a lot of sense. And even if it does, because so many times segmentation is about contract value, and we know that industries can use your tools in different ways. I think segmentation, I'll die on that hill, that it's a worthy exercise. But you're right. Is it done throughout? I don't think that it is necessarily implemented across businesses.

Andrew Marks: I don't think it's done well at the organization of it, but you bring up a great point. It's something that we teach about, segmenting your own book of business. Just because your company isn't segmenting or isn't segmenting right, doesn't mean that you, as the individual CSM, shouldn't segment your book of business.

Patrice Sawchuk: Yeah, it's very similar to. I was just going to say, it's very similar to relying on a health score versus CS sentiment. I think look at your book, understand how you are measured and what success will look like in your book. And from there, and it's not, again, like a health score, it's on a set and forget it. Your customers, they change, they mature, they go through their own life cycles, and so, you have to constantly be looking at your book and where do you need to lean in? Who needs extra TLC? Who's happy and sleepy? That's okay for a little while. You classify your own customers based on what you understand they need from you.

Andrew Marks: And that's constantly changing.

Patrice Sawchuk: Yes.

Andrew Marks: Right? What was a desired outcome six months ago? Okay, we hit that. All right, well what's next? Okay, now, we need to adjust the way we're looking at our customers so that we can make sure that we're measuring the effectiveness and the return on investment for the thing that's next. That's what you constantly need to be identifying and communicating value to your customers.

Patrice Sawchuk: And that's why activity metrics don't work.

Andrew Marks: Nope. A hundred percent.

Patrice Sawchuk: Back to Chad's point about looking at your book of business and how big are the contracts, because that's absolutely true. If you've got someone who's paying you, I don't know, a hundred bucks a month or whatever, that might not be the one you want to go after. You might want to go after the ones that are paying $10,000 a month or something like that. This also brings me, just made me think, when you talk about that, Chad, that made me think about these CSMs who, I don't know how they stay sane, that have these books of business that have 300, 400, 500 clients in them. They're like, "Well, I'm meant to be proactive to some extent." How do I do that? That's insane. But I would say-

Andrew Marks: You're reactive.

Patrice Sawchuk: A hundred percent. But I would say, if you want to try to be strategic, pick the top 10 clients on value and maybe potential for growth, and then, reactive on all the rest. I would definitely time block in that instance. And then, I would definitely try to do a cadence, but I wouldn't go crazy. Maybe once a month, because that's more than any of the others are going to get.

Andrew Marks: You're not a CSM. You got a 400 customer book of business, you're not A CSM.

Cinthia Silva: I know, but it happens all the time.

Patrice Sawchuk: Everywhere.

Cinthia Silva: All the time.

Andrew Marks: I know.

Cinthia Silva: Yes.

Chad Horenfeldt: Yes. I think, going back to the question about segmentation and is it effective, a lot of it is in the organization. The organization, it depends on how you work with Sales, because Sales sometimes have their own segmentation and they have their own definitions of what a CSM does. Oh, yeah, everybody gets a CSM. Oh, yeah. However what you want.

Andrew Marks: It's like The Oprah Show, "Everybody gets a CSM."

Cinthia Silva: You get one and you get one.

Andrew Marks: You get a car and CSM, yeah.

Chad Horenfeldt: Yeah. One of the unfortunate parts for CSMs is that a lot of it comes down to their leader. Is their leader actually a good marketer? What I mean by that is, are they marketing within their organization what their Customer Success team actually does and what does it not do? Is that very clear across the organization? If you ask a random Salesperson, "Hey, what is a CSM? What do they do here?" "Well, they do everything. They do Support." It's like, no, no, no. Then, you fail. It's hard. I have challenges too. But even just little things like, you have a meeting with your team, do you publish those notes in a public place where people can read them? Those little things that you can do to market what you're doing, the challenges that you have, creating cross-functional relationships, those things are really important. Cross-functional meetings, that's part of improving segment and why segmentation is so important.

Andrew Marks: Awesome. Let's get to the next question here, which by reading this question may take us to the end of our webinar. Anthony asks, "A hundred percent agree that every meeting with the client should be effectively strategic. The last thing we want as CSMs is to be time suckers. In the case that is an expectation that we meet with clients regularly, say bi-weekly, monthly, what are your best tips to make those recurring calls as effective as possible? How can we best use those calls to begin laying framework for success plans, business reviews, et cetera?" Chad, you want to jump in on this first?

Chad Horenfeldt: Yeah. I would say the first thing is, when you go into the call, before you go into the meeting, what do you want to accomplish? Ask yourself that question. Don't just throw a generic agenda. What do you want to accomplish? If you don't know what you want to accomplish, then you shouldn't have the meeting, because it's not effective for anyone. I think that's the first thing.

Andrew Marks: If you send me a meeting request without an agenda, I'm declining it.

Chad Horenfeldt: Even if it's an agenda, it could be like, go over new features, discuss issues. What do you actually want to get? Do you want to resolve a particular item? Do you want to get a customer to use a certain feature? Your own objectives might be different from what the customer wants, but that's okay, but at least have a sense of, what is it you're going to do? Then, the second thing is, based on what you want to do, create some questions around that. For example, if you know a customer is utilizing a particular feature and you know that's important to their outcome, then you prepare some questions. I see that you're trying to achieve X.

Andrew Marks: Why aren't you using that?

Chad Horenfeldt: That's right, but doing it in a way that ties back to their business. I see that we talked about this. This is being an important objective for you, and I've noticed that you're not necessarily using this part of the product. Maybe you can just give me a little bit more information as to why that's the case, asking that open-ended question, so coming prepared with questions. And then, we talked about this, the uncomfortable question. Asking the question such as, let's say, and this is like a Bob London-type question. If a competitor was to call you up today, what's the chance from 1 to 10, with 10 being for sure that you would take that call? Just asking, like really sticking the finger in there a little bit on the side and saying, "Hey, what would you do? How would you answer that question?" Anyway, that's what I'd recommend. Should come with a point of view as well, yeah.

Andrew Marks: Patrice, you got anything to add?

Patrice Sawchuk: I think my only thoughts would be very similar to the question I had already answered about not tracking activities versus outcomes. I think, in an effort to make your meeting as effective as possible, similar to what Chad was talking about, you've got to meet the customer where they are and understand what it is that they want to talk to you about. If you understand them and you surface up topics that they're going to be genuinely engaged and excited to talk to you about, that's where you can make those reoccurring meetings very exciting. And they need to be dynamic, because if they're reoccurring and there's just a static agenda, it's not going to be effective.

Andrew Marks: Know your audience. Give them a reason to show up. Maybe even in the invite email, tease something, "Hey, this is what you're going to get when you're going to show up." Know your audience, but you also need to be prepared, as we've all said here. Not just to ask the right questions, but to say the right things, because your C-suite executive and your middle manager and your end user, even if they're a power user and happen to be a champion, all have different definitions of success, and you need to speak their language.

Patrice Sawchuk: Yes.

Andrew Marks: Awesome. Anthony, thanks for the question. Chad, if you could hit the done button. Got another question from LinkedIn live. "I have a bad habit where I can't seem to leave things unread, so I struggle not responding immediately. Any tips to overcome that?" Chad, you want to jump in here? I already gave him a suggestion about the send later button, but Chad, what have you got?

Chad Horenfeldt: I'd say, the way I'd look at anything that comes in, it's like, the 2-minute rule. Can you respond right away? Respond right away. Does it need to response at all? If it doesn't, don't respond to it. And then, if it takes a long response, you can use some sort of remind me later. Set it for a time when you've designated to respond to these longer type of things. That's just a general approach. Think about this. Whenever you respond to something, you're going to probably get a response back, so do you want a response back? If you send a response on a Sunday or late at night, you're going to get a response back most likely. Just think about that before you respond.

Andrew Marks: Just delay your response, please.

Cinthia Silva: That's a good point, Chad, too, because if you respond on weekends or at night, that sets the expectation with your customer and your peers. All of a sudden, they're like, "Oh, Chad always answers at night. I sent you an email, you didn't respond." That's another way to not manage expectations is definitely outside of hours. I wouldn't make that a habit.

Andrew Marks: Send later. Every mail program, every CRM now has send later.

Patrice Sawchuk: Today's takeaway, send later.

Andrew Marks: Send later, exactly.

Patrice Sawchuk: No check-ins. No check-ins.

Cinthia Silva: Send later.

Andrew Marks: Right. We don't need the bell ringing and the, yeah. Because you do, you condition, you condition. What you end up doing once again is you end up creating your own problem. You create the problem that you're trying to avoid. Not everything needs to be responded to right away. Not everything is urgent. Not everything is priority one, so don't create the problem. Send later, time boxing. There's some really good tactical things that you can be doing.

Tactically, we've reached the end of today's session. I want to thank our guests for sharing their valuable insights and experiences, your contributions to make these discussions truly meaningful for our community. Thank you all, my Northeast contingency of OGs. To our audience, thank you for your active participation. Share your thoughts about today's session on LinkedIn by tagging myself, our guests, or SuccessHACKER. We love hearing about your takeaways.

Mark your calendars for our next and final CS Mastermind of the year. We're going to be announcing, by the way, a new format starting next year on December 17, when we'll talk about preventing burnout and maintaining work-life balance to finish up the year together. Finally, let me leave you with this great customer-focused individuals. No, they don't have all the answers, but they know where to find them, and that's why we've created this series. Have a great rest of your day and month. Have a great Thanksgiving break next week, for those who celebrate, and we'll see you in December.

CS Leadership Roundtable #59 Transcript: Creating Career Development Plans for Customer Success Professionals

For Customer Success leaders, building high-performing teams isn’t just about managing outcomes; it’s about investing in people. As CS professionals increasingly seek purpose, growth, and clear career paths, leaders must respond with intentional development strategies that align individual aspirations with organizational goals. Without structured career development plans, teams can become disengaged, top talent may leave, and customer satisfaction can suffer from high turnover and stagnant performance.

This webinar is critical for leaders who want to retain and elevate their teams while continuing to deliver exceptional customer outcomes. By prioritizing growth, leaders create a culture of engagement, ownership, and progression that benefits both employees and the customers they serve.

During the live CS Leadership Roundtable, the panelists discussed:

• Why career development is essential in Customer Success

• Assessing individual strengths and aligning them with growth opportunities

• Key components of an effective CS career development framework

• Building progression models for both ICs and team leaders

• Tying career development to business outcomes

• Low-cost ways small CS teams can support professional growth

• Ensuring equity and transparency in development opportunities

For this CS Leadership Roundtable event, host Andrew Marks was joined by:

• Eric Douglas, Strategic Customer Success Leader at FinThrive

• Keishla Ceaser-Jones, Managing Director, Partner Success and DEI ERG Leader at EAB

• Patrick James, CEO and Consultant at enroad

Top Takeaways 

1. Growth goes beyond promotions. Customer Success leaders can empower team members by highlighting opportunities for skill development, building specialized expertise, and taking on new challenges that showcase their strengths. By embracing a broader view of advancement, leaders create meaningful pathways for growth and development, even when traditional promotions are limited.

2. Transparency about business structure builds trust. Clearly explaining business models and structural constraints helps team members gain a better understanding of career paths and make more informed decisions about their professional development.

3. Competency-based frameworks drive development. CS leaders should implement clear competency models that define what excellence looks like at each level, from junior to senior roles. By tying goals to specific competencies and creating rubrics that outline expectations, leaders provide CS pros with transparent roadmaps for advancement.

4. Individual contributors own their career development. While leaders guide and support, CS professionals must take the lead by bringing agendas to one-on-ones and identifying ways to add value. Setting the expectation that team members dedicate weekly time to development reinforces ownership of career growth.

5. Cross-functional exposure expands career options. Opportunities for team members to grow and gain experience can come from adjacent departments. By allowing CSMs to move laterally throughout the organization, CS Leaders can help CS pros develop well-rounded skill sets while strengthening organizational knowledge and creating diverse career pathways.

6. Empowerment through business acumen drives strategic thinking. Customer Success leaders can teach team members to think strategically about their accounts by analyzing trends, assessing risk, and understanding the business impact of their decisions. By helping CSMs develop business acumen, leaders elevate their teams from tactical execution to strategic partnership.

Session Replay

Session Transcript

NOTE: The following transcript has been edited for clarity and content where necessary to improve readability.

 Andrew Marks: Welcome to the CS Leadership Roundtable, your monthly forum for actionable insights across Customer Success support and service. I'm Andrew Marks co-founder and architect of the SuccessCOACHING training program, and I am thrilled to be leading today's conversation on creating career development plans.

This learning series is brought to you by SuccessCOACHING, where we've trained over 40,000 professionals across 96 countries. Whether you're focused on Customer Success, Technical Support, or Frontline Service, our programs are designed to help your team deliver exceptional customer experiences. You can find all the details of our offerings on our website, successcoaching.co, or in the chat where Ashli has provided some links and coupon codes of anything special that we are going to be offering.

A few quick housekeeping notes. This session is being recorded and will be available next week with a transcript. Use the Q&A button at the bottom of your screen for questions. Higher upvoted questions get priority. And please keep the chat for commentary only. So, chat for commentary questions in the Q&A window. LinkedIn live viewers, you can post your questions directly in the comments, which will be relayed to us.

Now, what sets our roundtable apart is our focus on real-world applications. We bring together industry experts who share practical insights that you can implement regardless of your company size or customer engagement model.

Today I have three outstanding leaders joining me, and I'm going to let them introduce themselves to y'all and have them talk a bit about themselves before we get started. So, let's begin with introductions in alphabetical order with Eric.

Eric Douglas: Hi everyone. My name is Eric Douglas, Director of Customer Success at FinThrive, based out here in North Dallas and Prosper Texas. And no, I'm not a Dallas Cowboys fan, but I've been a Customer Success leader for about 18 years, leading teams at various organizations such as CBS Health, Optum, and now FinThrive, where we're focused on helping healthcare providers optimize revenue through technology and optimization.

So, one of my favorite parts about leadership is helping CSMs identify strengths and build careers that align with both their personal goals and the company's mission. I'm really excited and looking forward to sharing and listening to the experiences and learning from each of you today. So, let's go get it.

Andrew Marks: Awesome. Thanks, Eric. I appreciate you not being a Dallas Cowboys fan. As a Niners fan, it's important for me to throw that out. Next up is Keishla.

Keishla Ceaser-Jones: Hi everyone, my name is Keishla Caesar-Jones. I serve as a Managing Director of Partner Success at EAB, where I lead a national team that helps higher ed institutions drive measurable outcomes in their Marketing and enrollment solutions. But my real focus is really about building teams as a Customer Success leader, we have two customers. We have the customers that we serve with our products and services, but we have our internal teams that are our first customers. And when they're empowered and focused, we know that they're going to help us deliver results.

So, I'm really excited to have this conversation about how we keep a focus on the business, but also a focus on our employees to help drive retention in many ways in the work that we do. So, thanks for having me.

Andrew Marks: I love that. I love that attitude. One of my favorite leaders that I've been following for years is Sir Richard Branson and Sir Richard Branson famously said years ago, "Your customers aren't number one, your people are number one, because if you treat your people as number one, that's going to flow down to your customers." So, love that attitude. Thanks, Keishla. And last but not least, Patrick.

Patrick James: Thank you, Andrew. And hey, I'm Patrick James. I am in Northern California. Actually, we were talking about 20 minutes away from Andrew, and so I'm the CEO, Founder and I would say consultant of all things inside Enroad. What we do is we go out and work with managers to be more effective inside their organization.

So, we help managers around project management, project remediation, client remediation, turning around those projects and client relationships that have gone sideways. We've partnered with SuccessCOACHING here. We have the manager essentials course that I've constructed, and I also teach here part of the SuccessCOACHING team. And so, for the last 30 years leading up to enroad, I've worked throughout the entire customer journey for the last 30 years being customer focused my entire career. So, I'm very happy to hear and be here and talk about this because this is a deep passion of mine, working with managers, talking about promotions and career development.

Andrew Marks: Awesome. Thank you all again for making the time for us. All right. So, today we're diving into career development plans, a topic that's both critical, and if I'm being honest, one where I think we need to have a more frank conversation than most leaders are comfortable having.

Here's what we know, structured career development isn't optional anymore, and the data backs this up. 94% of employees say they'd stay longer if we invested in their development. That's not a soft metric. That's nearly universal. Our people are demanding clear growth plans, and without intentional development strategies, we lose talent, teams disengage and customers outcomes suffer. That's the business case and it's real.

But let's talk about what's also real. Most of us are building career frameworks and organizations where the math simply doesn't work. For example, we have 15 CSMs, maybe two senior positions above them, and we're having conversations about growth with all 15 people. We create development plans, we do the one-on-ones, we talk about aspirations, and then a customer escalation hits, a renewal goes sideways, and development gets pushed to next quarter again.

So, we find ourselves in this tension. And here's what makes this tension so frustrating, 83% of companies say developing leaders is important, but only 5% actually have programs in place. We're great at talking about development, we're terrible at doing it. We genuinely want to invest in our people. I believe that about everyone on this call. But we're also managing within real constraints, limited senior roles, relentless customer demands, budget pressures, and business needs that often require our best people to stay exactly where they are. Managing our most strategic accounts.

The question isn't whether career development matters. It absolutely does. The question is whether we're being honest enough about what growth actually looks like, what's genuinely achievable within our organizations, and how we navigate the very real gap between what our people want and what we can realistically provide?

So, today I want us to go beyond the playbook and talk about how we create development approaches that are both ambitious and honest, that invest in our people while acknowledging the real constraints we're all working within. So, let's start here. How do you balance giving your team genuine hope and opportunity for growth while being realistic about the constraints, whether that's limited positions, budget or business needs? Where's the line between being inspirational and being misleading?

And I'm asking this because 74% of employees feel blocked by lack of opportunity, not by their own limitations, but by organizational constraints. So, how do we address that honestly?

Patrick James: Yeah. I'll go ahead and start off. And thank you, Andrew for the question. So, I look at it first off, as we in customer facing roles, Customer Success, we're about building trust and we need to be truthful with our people. So, first off, the best leaders don't pretend that the org chart is just limitless. There are constraints with anything that we do. But what we need to do is focus on how each person can discover that they can leverage their unique strengths in what they do every day.

So, you mentioned the word "hope". Hope isn't about promising promotions, it's about helping people really see how they can grow within the role that they're in and how they can add value within the organization, but not necessarily through promotions. It's basically looking at it and saying, "Well, growth is not equal to promotion. It's looking and taking a much broader view than just a promotion."

Andrew Marks: I like that growth does not equal promotion. Sorry, go ahead, Keishla.

Keishla Ceaser-Jones: I was going to say, I like what you're saying, Patrick. I think it's about clarity and transparency. And most of the time the reason that I think a lot of leaders struggle with these types of conversations is that they haven't spent the time thinking about why their org is structured the way that it is. What's your alignment for your FTE roles? What's the scope of work that's assigned to it? And how do you build in-seat promotional opportunities that are about aligned to the performance and expectations you want people to meet? So, that you can still have in-seat promotion opportunities and growth at the same time, but it still could have its constraints by the business needs.

And so, a lot of times we don't do a good job of explaining to our team members our business model and our structure and why we are built the way that we are and what it takes to get to growth. I had a team member ask me once, "Hey, is there ever an opportunity that we're going to have another leadership role on the team?" I was like, "Well, let's talk about it. This segment of the business carries X millions of dollars to be able to support this. So, for us to get to that, we would have to grow the business by X millions of dollars to be able to create another role like that." And so, it wasn't that I wasn't saying, "You're not good enough. You don't have this or that. It's just really understanding the structures financially that we're built on."

Andrew Marks: Well, you're doing the math for them. And I love that strategy. You're pulling them in to better understand here's how the business runs, and somebody who wants to move into a leadership role needs to understand. So, you're giving them a taste. This is how the business runs.

Keishla Ceaser-Jones: Absolutely.

Andrew Marks: I've actually had people that wanted to get a promotion and I convinced them not to because it wouldn't be good for them. I'm like, "Well, let me explain to you what that looks like. So, I understand you want to promote you. You want to make more money? Okay. Let's figure out a different way of getting to that point." Because honestly, leadership is you think you're not going to enjoy it.

Keishla Ceaser-Jones: And it's not always more money. Leadership is not always just money.

Andrew Marks: No. Exactly.

Keishla Ceaser-Jones: There are some individual contributors who are doing better.

Andrew Marks: And I want them to. I always looked at my team members that exceeded their numbers and did better than I did. Okay, I'm doing something right. Eric, you got anything to add?

Eric Douglas: Yeah. I mean, if you look at just the nature of what Customer Success is and how they're built. Customer Success, they're growth minded by nature, and so they thrive on learning, problem solving and seeing progress. If you eliminate that culture from your organization, you most definitely lose your team.

And so, I think one of the things we're talking about is if there is an opportunity from your leader, if you're making X amount of dollars, if there's a budget, my thought is if I'm a top performer, I'm going to create my own opportunity. I'm going to identify where there's a gap, and I'm going to create an opportunity to be like, "Hey, I can do X, Y, and Z." And then when it's time, when that money is available for that promotion, I'm already a shoe in because I've already done it. I've already created opportunity. I already created the awareness of where we can achieve success as an organization.

So, it's not always going to be black and white. It's not always your leader's going to know the answer. So, you create something that works best for organization and for you as well. So, I don't wait on your leader to determine your career plan and your career growth. You are your own leader, you are the CEO of your business, of yourself. So, you create opportunity, don't let want to create that for you.

Andrew Marks: And I want to take that even a step further, especially for people and Customer Success, whose focus is on helping customers get value and building success plans and executing on those. Let's look at the parallel of my career path. I can build a success plan for my career. These are people who are thinking that way as part of their job. So, I would think that the percentage of people who bail are even higher for folks in this type of role because this is what they're dealing with. They're dealing with this process on a daily basis. Does that make sense? You all on the same page with me on that one?

Patrick James: Yeah. I'll also add is it's also changing the mindset inside your team or even in the organization is that it's not a career ladder. And that's where people get really hung up on the promotion. Track is to think of it as a career lattice and that a lot of times like a vine-

Andrew Marks: Ooh, career lattice, not ladder. Oh, I like that.

Patrick James: And so, you're going to grow, but sometimes you go out, you're going to go out to eventually go up. Because you need that foundation, you need those roots. And so, that's where you as a manager or leader, whatever, look for opportunities to put people in a situation or a role where they can be mentoring or they're helping others or they're doing special projects or often people call it creating heroes in every role.

And so, where can they take their strengths, their talents, and leverage those and expand their career? And so, if they're great at let's say collaboration. Okay, can they team really well with Sales and really show their collaboration strengths and everything like that? So, they're not just trying to go up the ladder, they're spreading out inside the organization and leveraging those skills.

Andrew Marks: And that's a great segue into my next question. When you are assessing individual strengths and aligning them with growth opportunities, do you have a process or a framework that helps you get beyond generic development conversations and create paths that are actually viable given your organization's realities?

Keishla Ceaser-Jones: I'll jump on that. I'm really fortunate to work in an org that has a really strong L&D culture. So, I really encourage leaders, you don't have to do this in a vacuum. You should be leaning on your HR teams and your L&D teams because the more consistency you have across your organization, the better.

And I think there's nothing better than to create to that lattice or Jungle Gym. We use the Jungle Gym framework, Patrick, maybe not everybody's going to grow in Customer Success. Maybe they're spending some time in Customer Success and they're going to move over to product or Marketing or something like that. And they take all of those great sensibilities that they learn.

In my org, we have very clear targets that our teams have to hit where I lead a commercial team, but we tie our goals to competencies. What are the core competencies? We're all flexing all kinds of competencies in the work that we do, but what are the top five or six competencies that matter most to that role that you want to help your teams develop?

And so, when I talk to my team, it's your goals are what you need to do, your competencies are how you need to do it. And you can create opportunities for your team members to flex up and grow. That competency might look a certain way at a manager level role, but might look how that competency exhibits itself at a leadership role might look different. And so, how do you teach your team members to start to see what's good for the customer and what's good for the business and flex up?

I kind of do what I like to call medical rotations in my teams, and so developing subject matter experts. And so, while I want to make sure that I'm leaning on people's talents and skills, I also want to make sure my teams are well-rounded.

And so, I will have rotations where my team members have an opportunity to sit on a product review board for a period of time, and we'll rotate that out. I won't just let one person who's a product guru do it. Everybody gets an opportunity to rotate through that. And so, they're getting to see the 360 view of the business that helps them develop, and it might also help them figure out what's a career path that they want to take from there.

Andrew Marks: It also breeds a sense of empathy for others in the organization that your team is working with and your team works with out of any other organization. People in customer facing roles work with more roles within the organization than anybody else.

Keishla Ceaser-Jones: Absolutely.

Andrew Marks: And that empathy is so important. And I think a lot of people and I always use when I go into organizations as a new operational leader, one of the first things that I would do is let's develop. And I would do it very quickly and we'd evolve it over time, but I always came in and said, "Okay. Where's your competency matrix for this?" And they'd be looking at me like a deer in headlights. What's a competency matrix?

So, we would very quickly develop a competency model matrix, whatever you want to call it. We actually have a Customer Success competency model. Ashli, can you find the link on our website where people can download, they see it and drop it into chat, please. So, we have a very fleshed out Customer Success competency model.

And then what you do is you create this rubric. It says, "Okay. Here's what good looks like at all these different levels." And once again, back to Patrick's point, it doesn't mean that people need to go up to management. It's say, "Okay. Here's where you're at now, and we have a standard role and we have a senior role and we have a principal role, and here's a career path that isn't an up and down, it's a vertical or maybe a slight increase. It's a different type of career path." But it doesn't always mean that everybody's got to go into management.

But I think a lot of teams are in this boat of not knowing where to start and not having something like this because they're running a million miles a minute, especially leaders are running a million miles a minute trying to keep all the balls up in the air. 70% of Customer Success teams don't have a formal enablement program. So, we're often in this position where we're building the plane wall flying. Eric, you got anything to add to this?

Eric Douglas: Yeah. I mean, most definitely, I agree. I mean, you can have leaders and individual contributor roles. And I think if you look at it from a sports team perspective, I know you talked about the 49ers and the not so Dallas Cowboys. I mean, everyone has a position to play. I mean, but there's just, you can have a leader that's not the quarterback. You can have a leader that's not the head coach.

And so, you can have those with sprinkle throughout your team, and that spreads and manifests to other team members, and they can see a path of where they can reach and be leaders themselves. And so, I think that's very insightful in terms of what type of team do you want to build yourself around? And I encourage my team to be leaders, even as innovative contributors.

Andrew Marks: I love that. You can have leaders without them having to be the coach. When I think of the 49ers staying on the football analogy, when I think of leaders of the 49ers, I think of guys like George Kittle. I think of Brock Purdy, the quarterback. I think of Fred Warner, unfortunately lost him for the year but I think of Fred Warner, the captain, the defense. It's not just about the coach.

Keishla Ceaser-Jones: And I think better than when a team member, nothing better than football than when a lineman gets to run the ball. That's the best play ever. When they run a pass play to somebody you're not expecting to.

Andrew Marks: Exactly. Or when they handed the ball to Deebo Samuel and he played as a running back.

Keishla Ceaser-Jones: Exactly.

Patrick James: Absolutely.

Andrew Marks: So, let's talk about-

Patrick James: Andrew before we-

Andrew Marks: Yeah, yeah, go ahead, Patrick.

Patrick James: ... move off, because for me, I think when you talk about frameworks is especially when it comes to career path and what frameworks, I just look at, again, I'm very tied to the Gallup CliftonStrengths binder to really understand what someone's strengths are. And let me even maybe use the word "talents", because talents are who you are. It's how you show up. It's your competency. It's your habits. It's your attitude. It's what really drives you. Some people talk about motivation.

So, talents are the strengths are who you are, how you show up. A lot of times people look at things like, well, what's needed for the role? And they focus in on skills or they look at knowledge, which there's knowledge which you know, and then your experiential knowledge. But really looking at what are your talents?

And when you look at a role that requires promotion, you have to really know what are the talents needed for that role. And so, for example, you mentioned empathy earlier. That's a talent. Someone who is in project management who is very disciplined around tasks and running that project and getting things done, that's a different talent where you get someone in Sales where they're fantastic at woo, or communication, networking, a room, that's a talent.

And you need to understand for those, and again, I'll go back to your math problem, those 15 people, and you got two slots. Well, what is needed for those two roles? So, your math problem becomes much simpler. You've taken it from looking at 15 down to possibly five people because you look at it and say, "Out of those 15 people that are in my group that I can only promote to." And you've already gone through like, "Hey, they're all really talented people." But I need someone who has strengths around executing.

Well, that's not all 15 of them. That may be five of them or maybe seven of them. But I also need someone who's talented in strategic thinking. And so, you look at that and say, "Well, oh, that's only two people on my team." And when I look at that, and I'm referencing the Gallup CliftonStrengths here, which again, we'll send out the links, you can actually look at what those themes are or those talents that Gallup outlines. And you can also look at Marcus Buckingham because if you're like, I don't know where to start in assessing my team's strengths, and what do each of those.

Clifton or standout. You can take for free. There's a pay, I think it's like $25 for the Gallup CliftonStrengths for you and/or your team to take it individually. So, you can start understanding what are those strengths that each person has, and then start looking at it, what do I need in that role? And that math problem you talk about becomes quite simple, I'd say simplified in that you can start going through a process of elimination and/or more exploration to understand what are my team's strengths and what do I need in those roles?

Andrew Marks: So, basically, you're suggesting that we use data to make some decisions about our people's career paths?

Patrick James: Well, it's additive because you absolutely have to have a conversation. Because if you're not having that conversation with your people, then you're missing out the most important component of it.

Eric Douglas: And Patrick, you're spot on. I think as you were talking, you might've said talent like five times. I read this book by Geoffrey Colvin, and it's called Talent is Overrated. And the way he talks about is athletes like Tiger Woods, Michael Jordan. Tiger Woods isn't talented. He was watching his dad play golf in the backyard when he was in his high chair at two years old. So, he built up the skillset by walking someone, and then he developed and worked hard at it.

And to your point of, you have to be able to meet with your team and know your team to understand what their skillset is and what brings out their talent, what their talent looks like, right?

Patrick James: Absolutely.

Eric Douglas: Because it's not that they walked into, their first job was Customer Success. They worked into the role of Customer Success, and someone said, "Hey, either you would be great in a client-facing role, or you'd be great at a project management role." And so, their talent and their hard work and determination put them into a Customer Success role.

And so, to your main point is that you have to know your teammate. You have to know your team. You have to know what skillsets to actually have in order to understand what the best development plan would be for them.

Patrick James: Absolutely. Well put.

Andrew Marks: So, by the way, my gardener is not too loud. You can't hear him in the distance, can you? Okay. Thank god. I just want to mention, by the way, we'll get to questions here in about 10 minutes, 10, 15 minutes. Oh, I see a few more added. So, please add your questions under the Q&A and any question that you see that you're like, "Oh, yeah, I want to answer that question," use that upvote button and we'll tackle those first.

All right. So, let's talk about the day-to-day tension. Customers need consistency and your best people on the most strategic accounts, but those same people need new challenges to grow. And they need time selfishly, I'm going to say this, they need time for enablement as well. So, how do you actually navigate that without sacrificing either customer outcomes or employee development?

Keishla Ceaser-Jones: Yeah. I consider myself a practitioner and you have to build in the time. I took over a team almost four years ago, and one of the first things that we did is we just integrated development in our work. And so, I run a rotation of meetings that are focused on commercial acumen, service acumen, and every one of those meetings, we spend half our time on the nuts and bolts, and then we spend half our time on micro learnings.

And so, it's integrated. We're always learning and building ourselves up and building up our capacity as it relates to our business cycle. So, I try to make sure I align the learnings, I don't want to go, we just recently did an end day a couple of weeks ago, and we spent some time really reviewing our service plans and thinking about how we run things. I wouldn't do that in the spring because that's headed into Q4 for me. I know my team's mind's not going to be in that space. So, I try to make sure that I do an alignment there.

I think about what the business needs and the skills that my team needs to develop, and I build that into the training that I do ongoing. I take time to do non-role-based training as well. So, we spend time on, we did a training on agility just recently and adaptive problem solving. So, you got to bring in that indirect learning that helps them know how to build their skills.

I love strength finder, Patrick. I think it's great, and it's just as important to know what your strengths are, to know what aren't your strengths, because those can be developed. I'm right-handed but I use my left hand. I don't use it as well, but I also don't just let it hang on my side as like a stump. So, we have to be willing to say to our team members, "Where do you have growth opportunity as well? How do you lean to your strengths, but know where you've got to build some capacity in some other areas to become more well-rounded, to be on that career path growth that you want?"

Andrew Marks: But most of the skills, whether they're physical, mental, they can be taught.

Keishla Ceaser-Jones: Exactly.

Andrew Marks: They absolutely can be taught.

Keishla Ceaser-Jones: They can be developed. Yes.

Andrew Marks: When my daughter was younger and she plays competitive soccer now, and she plays for a pretty high-level team. Actually, Patrick's been to one of her games senior play. But before we realized that she was a soccer talent, I was coaching her a local rec team. I taught her how to play using her right foot, but she's a lefty.

So, she actually, and I didn't even think about it because I know she's a lefty. We didn't really determine that she was a lefty until she was a few years older. Like, "Holy shit, she's a lefty." And she now is incredibly dangerous because she has a really good boot from the right or the left. She's really dangerous, especially when she's playing forward.

So, these things can be taught. The same thing with Eric, your story about Tiger Woods. He started processing and watching his dad, and then he went out and it's all about repetition. You want to get good at shooting hoops, go out and shoot 100 hoops every day. You're going to get better at it.

It's why when somebody says about our training, "Hey, there's content here that's repetitive." I'm like, "Yeah. It's designed that way on purpose. It's that repetition that caused it to stick in your mind." Eric, what do you got to add to this?

Eric Douglas: Yeah. I mean, you're spot on. The repetition, any trainings that you can take and can fuel your mind and to have you produce more and more and mor e, but I think it boils down to what you want out of your own career. Don't let anyone else determine your career. That's on you. A lot of times I like to say is that you manage your manager. Don't let your manager manage you.

You come to your one-on-ones with an agenda of what you want to talk about in terms of your career growth and what you want to see. Because your strength better than any leader does. You know what you're wanting to do and you know how to get there. It's just a matter of you having the confidence to do it. So, yeah, I love the models. So, yeah, that's my input on that.

Andrew Marks: Yeah. You own your schedule too. You make time for career development. We were on a call this morning a prospect call, and I said, "One of our best practices is you need to establish with your team that they're going to set aside 60 or 90 minutes a week for career development. And in this case, part of that is going to be consuming our enablement content, but you need to carve that time out." And they need to carve that time out on a weekly basis.

And the rule should be, if you've got a conflict, a business conflict, customer conflict, personal conflict, the rule is the agreement is that you will not delete that time, you will move it somewhere else. But you want to get people into this habit of career development and that repetition is the way that you create the habit. Patrick, you got anything to add that hasn't been covered already before we move on to the next question?

Patrick James: No, I'll just add one little piece plus one on everything that's been talked about. I would just say also look for as those skills or those competencies are looking to be built. Look for partnering opportunities, encourage partnering opportunities. I'll use myself as an example. I go to a big conference, networking, working the room. I partner, I ride the coattails of Salespeople. That is their talent. That is their strength.

Me, I'm much more of a small group. Let's dive into the details. Let's have a problem solving, very much more intimate type setting. That's where I really is my comfort zone. I enjoy that. So, that's why I go to a Sales conference. I'm like, "Look, I'm going to partner with you Sales guy. Let's go around and network the room because that's their strength." So, look for areas as they go to work on those weaknesses where they can partner with others to shine.

Andrew Marks: No, I was the same way. That was my MO when I was working with Sales teams. I'm the services guy. I know how to close business. I know how to go deep. But you do your type A personality stuff, I can handle myself just fine. But you take the lead. And we've been talking about this actually regularly recently, that we need to be looking at the revenue team as a whole, the revenue team as Marketing Sales, post-Sales and product. These four organizations are responsible for revenue in your organization.

So, we shouldn't be looking at the revenue team as Sales and then post-Sales. We're there to work together. We each have our role. And I know we touched on this a little bit before, actually Patrick did, but Keishla I know you had some thoughts on this. What does an effective career development framework look like when you're being honest about the math? How do you build something meaningful that isn't just retention theater?

Eric Douglas: Yeah. I mean, like I said, I'm super fortunate to be in an org that proactively thinks about in-seat promotion. So, every one of my Customer Success Managers came on board knowing I can get to be a senior Customer Success Manager by doing this level of performance. Super clear tied to objective performance and qualitative performance around competencies and a clarity of understanding of how long they had to do that for, how many revenue cycles that performance had to be in place for them to be considered for promotion. So, I love that I walked into a space that was already considering in-seat promotion.

And then I think what you want to do is just like I said at the beginning, is to be really clear about what people want to do. Not everybody on my team wants to be a Customer Success leader. And so, how am I making sure that I'm developing those other skills and competencies across the org? Whether they want to lean more operationally. Are they interested in product? And how do I create opportunities to build subject matter expertise that benefits the team, that benefits the business need, allowing for those side projects and stretch projects that are balanced and equitable?

I'm building an AI SME team that's working on different things and not everybody wants to do that. And so, how do I tap into the people that want to stretch in a particular way and give them those opportunities, but that it's also in a way that's feeding the team, but being transparent about the type of team that I have.

And so, if they're ready to grow as a commercial leader, then we can talk about those things. And that might not be on my team, that might not be in my org either. And that's okay. And so, we have to be willing to say, "I'm going to make you the best you are here. And that growth might not take place here, but I'm going to get you ready for whatever it is you want to do next."

Andrew Marks: I always encourage my team if there was something that I thought was a better fit in on another team in my organization, I always encourage them. I say, "It would be a bummer to lose you, but I also want to support your career growth. And all I ask is that we've figured out some sort of transition, so it minimizes the pain for the rest of the team and the customers."

But that was something I was always talking to my team about. "Hey, if you think there's a better opportunity over here, I will support you. I will do whatever you need. I will speak your praises to that leader." Because I'd rather have that person stay within the company than go somewhere else. That lost domain expertise is detrimental to the company.

Keishla Ceaser-Jones: Yeah. It's so important organizationally. And when we talk about CS leaders having a seat at the table, this is a great opportunity for Customer Success leaders to be influential across Product, across Marketing, across Sales, where we have an opportunity to add value to the organization because we are building customer voice employees that can go off and be in other parts of the business. It only strengthens the business.

Andrew Marks: Oh god, yeah. I loved it when I had people that said, "Hey, I want to get a product.". "Yeah Because I know that you're going to share the message with product of what we're missing that makes our jobs difficult. So, hell yeah. What can I do to push you in there?" Eric, you got anything to add?

Eric Douglas: No, I was just writing that down in terms of getting into the product, because I know some of the CSMs on my team, they want more product access, but I can most definitely see the benefit. I know, Keishla, I was listening to you and one of the things that I was thinking about was I take the non-conventional way of just throwing some of my team members into the deep end and see if they can swim, focusing on, I know what their weaknesses are and they know what their weaknesses are and they steer away from their weaknesses. I throw them into the deep end to work on the weaknesses versus the strength.

I already know where you're strong at. I want shift you expand and grow, so I'm going to challenge you and put you and expose you to other avenues so that you can grow. Because I don't want you to continuously grow towards your strength. Let's focus on your weaknesses. So, that's one of the things that I do with my team because it helps them to balance out and get over fears.

And then once they start to get over those fears, they tend to grow, their confidence tends to blossom. And then throughout the organization, leaders see that. And so, when leaders see that, then you want your name to be called out during meetings where you're not attending. It's about you showing your worth and you showing your value throughout the organization without speaking.

Andrew Marks: Now, all that being said though, I think this is where we need to get creative because Customer Success actually has incredible career flexibility. People can move into operations, they can move into technical CSM roles, they can move into customer education, onboarding, customer Marketing, all without needing a traditional promotion or to leave the organization. So, are you actively surfacing these as legitimate growth paths, or do they feel like consolation prizes?

Eric Douglas: That's a great question, because I don't necessarily know what other departments have on their roadmap in terms of openings where I can see a particular team member sliding into one of those openings. When they're playing during their annual planning, they might say, "Hey, we're thinking about adding headcount for this role because we need support on these products in this area, in that area."

And I think that's where CSMs need to exhort themselves during meetings because that leader may think, "Hey, I heard her talk, I heard him talk and he did a pretty good job on his project. I can see that person in this role that I'm creating in 2027 or 2026." So, I think that's a valid question. So, I'm not sure if I answered it correctly, but I gave it a shot.

Andrew Marks: Well, there's no correct answer. I think it's more of a rhetorical. I think if anything, it's a rhetorical question for everybody.

Keishla Ceaser-Jones: I think it's important for leaders to, you have to stay in touch with what's happening across the org and how do you make sure that you create a culture? I mean, I'm always looking for jobs. You should always be paying attention to what's out there. Number one knowing what's next for you is a little bit of opportunity. You got to have a little luck and opportunity coming together at a right time.

And so, I encourage my team, "You should be checking our internal job board and seeing what's going on." Our org also promotes the idea of these, they're called internships. And so, on a cycle, teams will put out a call and say, "Hey, we maybe have a special project that we want to do." If somebody wants to come and intern in another part of the firm, they have an opportunity to just see, maybe, I don't know what it's like to work over on this side of the business, and I don't want to go and take a job. I don't know if I want, but I want to explore a little.

And so, I think it's really important for orgs that where you have that capacity and people are performing the way that they should, they can do a little bit of something side of desk for six weeks to get a taste of what operations is doing or what Marketing is doing that. Those are great ways to stretch.

And I think it's just about getting creative, but also being thoughtful that you can do that and maintain the business. And sometimes in smaller orgs, it's tight because already wearing a lot of different hats. And so, it can be a stretch.

Patrick James: I think it comes back to a couple of things of making sure that your one-on-ones are very effective, that you're communicating with each other very candidly. And what that is, so it doesn't feel, and I'll use your word here, Andrew, that it doesn't feel like a consolation prize. That you can clearly articulate the value of how this particular task or this particular body of work is adding to the value of their career, their interest building upon their strengths and/or setting them up for future success.

So, that's on you to have that very candid conversation. Which then leads me to making sure that your one-on-ones are not status reports all too often. I see what happens is we talk about this career thing, and I go into organizations and I sit and I go, "Look, I'm going to shadow you on your weekly one-on-ones. Or hopefully they're weekly or every other week, or at least I hope you're doing them."

So, when I sit there and I listen and I'm like, "All they're talking is talking about projects and what's going on in their projects." And I go, "Let's talk about how a one-on-one is supposed to be structured." Because that's about the individual, or I see the manager spending 90% of the time talking, and I'm like, "This isn't a one-on-one, this is all about your projects and your business." That's a whole separate-

Andrew Marks: Which is something that should be shared in an email. We want to talk to people. So, what role should individual contributors playing in driving their own development versus what the company provides? How do you foster? And you touched on, I think Keishla you touched on this a little bit earlier, but how do you foster ownership without it becoming an addiction of leadership responsibility?

Keishla Ceaser-Jones: Yeah, 100%. It's your career, it's your job to own that development. I think it's 70-30, 75-25 split. My job as a leader to help you understand the business structure and what opportunities there and to create an opportunity for you to grow and skill and capacity and those types of things. But what you want to do, I don't know that. I don't know what it is that you want to be when you grow up.

Andrew Marks: You're there to facilitate that.

Keishla Ceaser-Jones: I'm here to facilitate It and guide it. And I could see talent in you and think, I've had people who are like, "Oh, for sure, that's my next leader, my next manager." And they have no desire whatsoever. And so, they have to be able to articulate what matters to them, how they want to grow.

And then it's for us to then create where within the business construct. Can I help you flex that skill, develop that muscle, and improve that thinking? And so, I think it's so important for the ownership. It is definitely on the team member, and it is for me to create space.

I do skip level meetings with some of my team members on a regular cadence, and that is their meeting. They own it. I don't set the agenda. I'm like, "What are you here to talk about?" And I would have some of them come in and they're talking to me about the business. I'm like, "First of all, that's your manager's job to do that. I don't want to talk about that. How do you want to use your time with me and engage?" And we do not have to talk about this account or that account or this project or that project.

And so, I think to that point, Patrick right, there's a time and a space for that, but you should dedicate carved out time. That is very clear that we are focused on skill development and focusing on what is important to you in developing in your career.

Andrew Marks: Eric, what's your perspective on that? Similar, different to you? I mean, do you have different division? Is it 70-30, the individual? What's your take?

Eric Douglas: I would say yeah, probably 70-30. Here at FinThrive, we do have a good training program, of course, but I think it really boils down to the individual because leaders, I'm not sure if CSMs realize this, we have so much on our plates. And then we really and authentically want to be engaged through our one-on-ones.

But I'm going to be honest, sometimes we probably disengage a little bit because we are trying to carry the business and trying to put out fires for you all and keep things away from the team, and we take on that burden. And then when you guys come and have meetings, it's not always going to be a great day.

And so, that's something you all have to realize from a CSM perspective is we want you guys to be the best that you can be. But sometimes those meetings can be a drain for us, just to be honest. But then we do want to get the most out of it. And so, that's where it comes to you bringing the agenda item, you come in so that we are engaging as a partner with you in your career development. And so, it's not just a dialogue where I'm advising you and telling you what to do and being a professor and talking at you. It's a conversation of what works and what doesn't.

Andrew Marks: Right. For collaboration. Patrick, before we're going to move to questions for audience questions next, but Patrick, before we move on, putting on your consultant cap, given that you consult on this very thing on a regular basis with leaders and teams, how do Keishla's and Eric's approaches resonate with you?

Patrick James: I think it's great what they've been saying. I think that around the strengths and about meeting with the individual and being curious as managers and leaders, I think that for me, that gives me, I'll just, for lack of a better word, warm fuzzies. Because when I hear that, people are like, "Hey, I want to spend time. I want to get to know you."

I mean, when you look at the data, when you look at what at the end of the day, what people want to say in the workplace, and Gallup has done a ton of studies around this, it comes down to two things that an employee can say, "I'm able to use my strengths every day at work, and I know what is expected of me." Those are the two things that the studies, Gallup has written numerous studies about that. It goes back to also what they call their Gallup Q12, which has to do with employee engagement.

And I go for everything that we've talked about here, those are the building blocks so that employees can say that. "Hey, here, what are your strengths? Let me figure out how we can deploy those." And then that leads into them knowing what is expected of them. I'm expecting you to use your strengths. I'm setting up a role. I'm having a career development plan that we're going to execute on.

And oh, by the way, those are going to be tied eventually two OKRs or objectives and key results for the organization. But it's all going to come together simply by a manager being engaged and being curious.

Andrew Marks: Exactly.

Patrick James: Or put it in another way, something we say in management essentials is, what do employees really want is to know me, to engage me, and to empower me. And that's also rooted in science as well and data and surveys. But go, if you know them, you engage with them and you empower them. And that's what we've been talking about today. So, I'm very excited to hear and share what we've done and talked about today.

Keishla Ceaser-Jones: I'll tell you that word "empower" is so critical. Oftentimes our teams are not performing to the capacity that they can be because we are holding onto the power as leaders. And if we could let that go, I've given my team frameworks for how to operate and they understand, it's not, "I made a better decision than you. Here's the business basis for why I'm doing it, why I think the way I think, why we're doing this the way we need to do it."

And if we teach our teams to understand how to not just do what's nice for the customer or what they're asking for, they're demanding this product feature update. Is there an ROI on that? Teaching them to understand that and empowering them with that knowledge, that's how people grow because then they're able to lift above their task and their projects and their deadlines and see the bigger picture, and it helps them to start to think strategically for you. And so, empowerment is so key. I love that word.

Patrick James: I want to first off, give you a high five here, picking up on the empowerment and build off of what you just said because all of a sudden you probably saw me perk up and get all excited here. And that is on the empowerment. One of the questions that we get the most in manager essentials course is about how do I motivate my employees? Well, let me turn it into drive. And a great example and a great book on this is Daniel Pink's book Drive.

Keishla Ceaser-Jones: Exactly.

Patrick James: When you talk about empowerment, what do people want? Autonomy, mastery, and purpose. And what are you doing as a manager, as a leader to create an environment that you can empower people and create that drive in those people. So, Keishla, your spot on.

Keishla Ceaser-Jones: 100%.

Andrew Marks: Awesome. Let's get some questions. By the way, just a reminder, folks, if you've been with us before, we do go until a quarter past the hour. There's only five questions, so we'll get through as many of these possible between now and about 14 minutes past noon Pacific. So, our first question comes from Clay. Clay, good to see you. Although it looks like you had a drop-off, but I'm sure you'll watch this in the recording on the platform. Clay asks, "I would love to hear how you have structured your teams to give ICs a career like junior, senior staff, et cetera."

I have plenty to say on this. I touched on it earlier, but Patrick, look like you want to jump in on this. By the way, for my other Eric, Keishla, if you want to check out the Q&A, if there's any questions that jump out at you that you want to jump into, hit that answer live button. But Patrick, what have you got for Clay?

Patrick James: Yeah. I think I wanted to know a little bit more, A lot of directions you can take this question, but I look at just the structure of the organization and what we can do as an organization to support our customers. And like, "Okay, sure. Do we want to have a really flat organization? Do we need to have a little bit more structure into it?" And that's why I wanted a little bit more, but I like the flat organization type of model.

But I go, okay, so in each of those roles, what do we need from a junior staff person to a senior staff person to eventually a manager? What are those skills? What are those, again, we talked about competencies that are needed in each of those roles and somewhat having maybe a development expectation framework for each, but we're very, very clear as to how we're going to structure those, but also why. Why do we need this role?

And you've got to continually ask yourself that. So, it's like if I'm creating another layer just to give someone a sense of feeling of promotion or somewhat status in the organization, well, that doesn't really serve organization. That serves the individual, not the organization, and more importantly, not the client.

And so, you've got to sit there and look at every single role and say, "Look, can I then, instead of having another layer, can I create a hero in this role." And say, "Look, you're a specialist. You're a specialist in let's say this particular industry or this particular size of client." And therefore, instead of creating all of these layers, I've got a layer here and I'm creating specialists within that.

Andrew Marks: So, I think there's a need for specialization, but I also think that there's a need for, it's like the level of expertise level. So, when I was at Birst cloud business intelligence, we had junior folks that their job was to design a data model, an initial data model, but my senior folks were the peer review of the data model, and these were people that had X number of years more experience with data modeling.

And then there was a different level that was responsible for going beyond the data model and building the ETL scripts, which need to be freaking dialed in order to pull data from various systems and populate the data model. And so, we would create a competency model, we'd develop a skills matrix, and we would create a rubric that would say, "Here's what good looks like at each one of these levels." Because you can't just create a career path and say, "Here's your career path." You got to define it. You got to be really specific about, and here's how you move from one level to another.

Patrick James: Absolutely.

Andrew Marks: That's really important too. You got to give people a clear understanding of what good looks like.

Patrick James: Yeah. When I said developing extra framework, that's what I'm at. So, well said. Thank you, Andrew.

Andrew Marks: Yeah. Keishla. Eric, anything to add to Clay's question?

Keishla Ceaser-Jones: Patrick handled it.

Andrew Marks: Awesome. All right. Pat, I'm sorry, Eric, did you add something to add?

Eric Douglas: No, no. I like what you said, the direction, clear path, I think everyone works better when things are clear, but other than that, Patrick hit it right on the head.

Andrew Marks: Pat, if you need to hit the done button on that question. Clay, thanks for the question. Like I said, I sure you'll watch this later or I'll get an email from you. Clay's a customer of ours. Our next question comes from Ola. Ola, always good to see you. Thanks for joining us again. Ola asks, "How can CS leaders effectively encourage and support upskilling within their teams, especially in areas like business acumen or strategic thinking? How can we motivate and create opportunities?"

Eric Douglas: I think from a CS leader, you demonstrate what that looks like first off, and then you expose your team to different meetings that they can attend to see what those meetings look like, to give them an idea reference of course material. But I think I'm all for exposing the team to different avenues, whether it's executive leadership meetings, project meetings, or just exposures is key to encouraging your team to see and be exposed to different avenues to grow.

Keishla Ceaser-Jones: Yeah, I agree with those [inaudible], Eric.

Andrew Marks: Keishla what do you got?

Keishla Ceaser-Jones: I think it's equally important to just teach your teams how to talk about their business in strategic and thoughtful ways. If every time you talk to your team member in their one-on-ones or whatever, you're in the task, in the nuts and bolts and you're not looking, "Tell me about the trends you're hearing. What's your analysis of your risk? What's your risk assessment?"

You have to teach them how to think about their business. They're all running little small businesses, so teach them business acumen in their world, and then you create the foundation to be able to scale that up.

Andrew Marks: I think you need to, I'm going to take this step further. I think you've both been dancing around the net-net of this. You need to teach them, you need to explain to them the what and the why.

Keishla Ceaser-Jones: Why. Yeah.

Andrew Marks: It's the what and why. The what is the business acumen or the strategic thing, and the why is I'm going to connect the dots for you and you got to do the math for them. You need to understand business acumen because this is going to have this impact on your career, on your business, on your customers, on our business.

Keishla Ceaser-Jones: And my measure as a leader is I'm not getting contracts signed. That's not my job. My measure as a leader is how well I create the conditions for my team to execute towards their goals, and that is giving them good pricing strategies or good product alignment and things to go and help them run it, retaining the customers, but they can be doing those same things at their level is, you can't come and tell me, "Oh, this person loves me and that's why they send their contract?" No. What are the conditions that you created in your business that led to that success?

Because ultimately the work of Customer Success is to find the path of least resistance, the lowest common denominator that gets our partners to the success, not overdoing it, not doing team too much. I say this all the time. Usually we check ourselves, we find ourselves doing too much and get too little on return, and we over index on things or under index on things, whether they work or not, but I need you to tell me that, "Hey, I had five ROI conversations and those five ROI conversations had this impact."

I need to know that what are the strategies that you're deploying? Because we either got to stop it, start it, or continue it. What are we doing? And I need that information to know what's working, what's not, so we can reset our strategy and we have to teach our teams to not overvalidate things or undervalidate things and really understand what's happening in their business.

Andrew Marks: Patrick, what do you got to add to this given that you have that course where we talk about this?

Patrick James: Yeah. Sure. Absolutely. We talk quite a bit about this. There's two questions there, and I'm just going to focus on the second part around motivate and create opportunities. How do we motivate and create opportunities? We are talking about a little bit about motivation, and again, numerous people will say, "Look, motivation, it's fickle." I mean, think for example, working out. Some days you feel like it, some days you don't, and so it's fickle.

What it is, what drives people? And again, I'll reference back to Daniel Pink's book called Drive. I'll even drop in the thing. There's a video out there, you can Google it all. I'll even drop it in the chat here to go out and take a look at it, which leads to the second part of how do I create those opportunities.

Think of it like a coach, a coach on a professional basketball. I think of Steve Kerr. He's got a stacked roster of talent on the team, but they work on their individual contributors that come together. They work individually on their talents. They work at becoming a better player, but Steve Kerr and the coaching team creates an environment where they can be driven. They're all going towards a vision so that you as a manager, so I think get sometimes out of the hat or wearing the hat of being a manager and go, "I got to put on the hat of being a coach and understand what a coach does." Read about it and understand it, and that will help you get to that level and taking your team to creating that driven Type of environment.

Andrew Marks: Awesome, Ola. Thank you. Let's see. All right. I think we got time for one or two more questions. Our next question comes from Virginia. Virginia, thanks for joining us and thanks for the question. "I love upskilling my team and I try to work on skills that are not job specific, learning styles, time management, communication skills. I'm having trouble getting my leadership to see this as valuable because it's not a CS skill. I'm sorry, time management, communication are all CS skills, by the way. How do you illustrate value to leadership so that you can tell your team to respect that time in their calendar the same way they would any other meeting?"

Eric Douglas: That was a lot in that question. Yeah. I think value time in a meeting, I'm trying to understand, which is a Virginia.

Andrew Marks: So, time management, I look at things like time management, communication, empathy, active listening, storytelling may not, for example, you might not think Customer Success, but it's 100% Customer Success, and especially since we released our Value-Based Selling Program a few months ago, we've been talking to a lot of customers and prospects about the impact that a trained Customer Success team can have on your book of business, a trained Customer Success team, whether it's value-based selling or our CS foundations, we have data from our existing customers that say they attribute anywhere from a three to 5% increase in retention and/or expansion to trained people.

If you've got a hundred million book, if you've got a 10 million book of business, do the math. What's three more percent? Forget 3%. What's 1%. 1%. Wait, if you can't commit to a 1% improvement in retention or expansion, you're basically saying the people who I have on my team are unable to be enabled. They are unable to grow.

So, do the math for them. I mean, that's how you convince your leadership when you do the math, because it's going to be really hard. Even three to 5% improvement is hard to argue, but 1%, super hard to argue. If I have $100 million book of business and I can guarantee you a 1% improvement, 1%, it's a million dollars.

Keishla Ceaser-Jones: Yeah. I think too, if you're working on communication skills, have we reduced customer complaints? If you're working on time management, have we been able to speed time to onboarding or different things? I think there's some ways to quantify these things for leadership.

I think for your team members, it's really about connecting it to the work. I think if you do training standing alone, it feels nice to have instead of need to have, it's like how do you make sure whatever competency-based training you're doing, you want to make sure you're feeding it back to the work, but all of that that you said, Andrew.

Andrew Marks: And Virginia, if we're not already connected on LinkedIn and message me, I actually have some statistics from everything from Bessemer to Harvard Business Review and a couple other places that talk about, "Hey, an educated enabled team translates into more Revenue for the organization." And you can point instead of you saying that to them directly, you can say, "Hey, look at what these articles from well-respected sources say."

Eric Douglas: I like that.

Andrew Marks: Awesome. Okay. Last question from Danielle, and I'd like to get a response from all three of you. Can you touch on career development for team leads and managers? What's the development plan look for them? And Patrick, I want you to go last because I want you to talk about management essentials, so I think that's exactly what that is. But I mean, Eric, Keishla, how do you handle career development for leaders?

Eric Douglas: I know for me, my team leads and I have them stepped into my role and I take a step back. I have them do some of the leadership responsibilities to give them a taste to what that looks like. Attending meetings, leading team calls, managing products projects, and driving the results of that, but then at the same time, showcasing to the whole or what their performance is and have them get accolades for that and make sure I call that out.

Andrew Marks: I Love that. Do my job. Do my job, see what it's like. What about you, Keishla?

Keishla Ceaser-Jones: I think really being clear on the domains within your business and making sure that you've got clear swim lanes, areas of responsibility where they have an opportunity to be a leading voice in those particular areas, so I mentioned that I do those rotations. We divide spending time on commercial versus service support work and then letting them shadow you, being transparent.

If I have to go to Rev review and talk to my senior leadership, I come back and I have that same conversation with my team. I'm being really transparent and letting them know what the challenges are and letting them be a part of setting our strategy and our plans for the work that we do in our business.

Andrew Marks: Wrapping things up, Patrick, before we close the webinar, what do you got?

Patrick James: I'll just repeat the question. How often are managers checking in on performance development plans with CSMs once a quarter, once a month?

Andrew Marks: No, no, no. Can you touch on career development for team leads and managers? What's the development plan look for them?

Patrick James: Yeah. I think the development plan is one of the things we do in manager essentials is provide all the templates and structure on the career development plan. Like what is the structure? How do you go about segmenting the work, having a plan, building it into your one-on-ones? What goes into your performance review beyond what your company is using a performance review process?

So, developing that structure so that it's just part of the natural flow of your daily or your weekly one-on-ones or bi-weekly one-on-ones so that it's just at the end, it's not a surprise. So, it's all built into the framework.

Andrew Marks: Awesome. Okay, folks, we've reached the end of today's session. I want to thank our guests for sharing their valuable insights and experiences. Your contributions make these discussions truly meaningful for our community. To our audience, thank you for the active participation. Please share your thoughts about today's session on LinkedIn by tagging me our guests SuccessHACKER or SuccessCOACHING. We love to hear your takeaways.

Mark your calendars for our next CS Leadership Roundtable on December 12th when we'll discuss delivering personalized customer experience at scale. And I believe we'll be at a point where we can announce our new structure for our webinars. I believe in December. I would hope so, Ashli, right? We're going to be ready to launch the new program?

Ashli: I believe so, yes.

Andrew Marks: Yeah. Awesome. So, we'll share all that also, so on December 12th. So, make sure to join us on December 12th to check it out. Finally, let me leave you with this great CS leaders know they don't have all the answers, but they know where to find them, and that's why we created this series. Have a great rest of your day and month and we'll see you in December.

The way you deliver Customer Success directly impacts your bottom line. Whether you deploy highly specialized Customer Success Managers focused on a handful of critical accounts, or leverage digital tools to deliver personalized service at scale, your methodology shapes the entire customer experience. Choosing the right approach is crucial: studies show that customers will pay more for an excellent experience, demonstrate stronger loyalty, and are more likely to expand their relationship with your brand.

Here’s a breakdown of Customer Success methodologies, including how to decide which one is right for you and the steps for smooth implementation.

This article will discuss: 

• Understanding Customer Success methodologies

• How to choose between the three methodologies 

• Key questions to consider before choosing

• Implementing your chosen methodology
  
  

Understanding Customer Success Methodologies

To find the right Customer Success methodology, it’s essential to clearly understand the three primary models: high-touch, low-touch, and hybrid. Each offers distinct benefits and potential challenges.

1. High-Touch Model

A highly personalized, engaged Customer Success methodology where Customer Success Managers work closely with a smaller number of accounts, using a consultative approach. Engagement is frequent, strategic, and tailored to each customer’s unique needs.

Key characteristics: 

• A dedicated CSM for each account (or a very small number of accounts).

• Frequent check-ins, in-depth quarterly business reviews (QBRs), and strategic planning sessions.

• Deep understanding of customer use cases and challenges.

• High levels of customization in everything: onboarding, training, and ongoing support. Research shows that more than 70% of customers expect companies to deliver personalized interactions, and even more get frustrated when that doesn’t happen. 

When it works best:

• Enterprise or complex accounts.

• High-value contracts where retention and expansion have a significant impact on a business’s revenue.

Trade-offs: 

• Resource-intensive (limits the number of accounts per CSM).

• Requires experienced, skilled CS professionals who have domain expertise in their customers’ fields.
  
  

2. Low-Touch Model

A digital-first Customer Success approach that leverages automation and self-service resources to drive adoption and customer engagement, and to reduce the need for manual CSM intervention. 

Key characteristics: 

• Automated onboarding sequences and product walkthroughs.

• In-app tips, emails, and customer health score monitoring.

• Self-serve knowledge bases and webinars for customer education at scale.

When it works best:

• Customers with straightforward onboarding and adoption.

• Products that are not complex and don’t require customization.

• Companies prioritizing scalability and cost efficiency.

• Customers comfortable with self-guided learning and digital support.

Trade-offs: 

• Less direct CSM engagement with the customer.

• Risk of missing nuanced feedback and revenue signals without human interaction.
  
  

3. Hybrid Model

A flexible approach that blends high-touch and low-touch tactics based on customer segment, lifecycle stage, or specific needs.

Key characteristics: 

• High-touch engagement for strategic or at-risk accounts.

• Low-touch automation for long-tail or healthy accounts.

• Dynamic segmentation (customers may move between tiers as their needs change).

• Ability to scale CS services without sacrificing strategic relationships.

When it works best:

• Businesses with diverse customer segments and varying user needs.

• Teams looking to balance efficiency and personalization.

• Organizations that want to provide tailored experiences without overextending their CSMs.

Trade-offs: 

• Requires robust customer segmentation, KPI tracking, and CS tech to execute effectively. 

• Risk of inconsistent experiences.
  
  

High-Touch vs. Low-Touch vs. Hybrid: How to Choose

Selecting the right Customer Success methodology for your organization is crucial because if you choose the wrong one, you could harm the customer’s experience and your business. Customers who require a higher level of personalization will feel neglected, or you could over-provide for customers who don’t need it.

Here are factors to help you determine whether a high-touch, low-touch, or hybrid strategy is best for your organization.

1. Customer Segmentation & Product Complexity

Start by analyzing your customer base. If you have a smaller number of high-value customers who require hands-on support to achieve success, then a high-touch Customer Success methodology may be the best approach. If your products are intuitive, quick to onboard, and have a large user base, low-touch might be suitable. Meanwhile, hybrid allows you to match the level of interaction to each customer segment (for example, high-touch for enterprise clients, low-touch for smaller accounts).

2. Business Resources & Goals

Your company’s Customer Success objectives and internal capacity should also guide your choice. If your top goals include retention and upsell among a small, strategic customer set, invest in a high-touch approach with dedicated CSMs. If scalability and cost-efficacy are priorities, low-touch digital-first CS programs can maximize reach without ballooning costs. 

3. Technology & Data Readiness

Your tech stack and analytical capabilities will influence what’s feasible. Low-touch and hybrid models often depend heavily on automation tools, product analytics, and customer health tracking to function effectively without missing touchpoints. 

Key Questions to Consider Before Choosing

Before committing to a Customer Success methodology, run through a decision-making checklist to ensure your choice aligns with your customer needs, business strategy, and operational capacity. These questions can help you pressure-test your approach:

1. What are your business priorities right now?

Are you focused on maximizing retention for a small set of strategic accounts? Do you need to scale efficiently to reach a large number of customers without adding headcount?

2. How complex is our solution and the onboarding process?

Does your solution require consultative training and hands-on guidance to deliver value? Can customers achieve success through self-service resources like knowledge bases?

3. What is our customer segmentation strategy?

Can we clearly define which customers require high-touch or low-touch engagement? Do we have a system in place to dynamically move customers between tiers as their needs change?

4. What’s our team capacity like?

How many accounts can each CSM realistically manage without compromising service quality? Do we have budget for specialized CS roles, or will we rely heavily on automation?

Implementing Your Chosen Methodology

Once you’ve decided which Customer Success methodology best aligns with your customer needs and business objectives, the next step is putting it into practice. Here are steps you can take to execute your methodology.

1. Map the customer journey for your model: Outline every stage of the customer lifecycle (from onboarding to advocacy) and identify key touchpoints that match your engagement style (such as in-depth QBRs for high-touch accounts).

2. Select the right tools and processes to support it: For high-touch, develop processes your CSMs will use to engage customers, and consider tech like scheduling and project management tools. For low-touch, ensure you have strong automation tools.

3. Train your team: Regardless of the methodology you choose, you must train your team. Provide clear playbooks that outline when and how to interact with customers, and offer targeted Customer Success training to refresh core skills. For hybrid teams, train on dynamic segmentation so CSMs know when to shift accounts between models.

4. Build feedback loops for continuous improvement: Collect feedback from both customers and your CS team about the effectiveness of your methodology to inform improvements. Also, use data insights (such as adoption rates, NRR, and churn drivers) to monitor and adjust processes as customer and business needs evolve.

Whether you lean towards a high-touch, low-touch, or hybrid model, the key with a Customer Success methodology is alignment: you should match your model to your customer segments, product complexity, and overarching business goals. 

Frequently Asked Questions About Choosing a Customer Success Methodology

What is a Customer Success methodology?

A Customer Success methodology is the structured approach your team uses to engage with customers, drive product adoption, and ensure long-term retention. It defines how frequently you interact with customers, what tools you use, and the processes you follow to help them achieve their goals.

What’s the difference between high-touch and low-touch Customer Success?

High-touch CS involves personalized, frequent interactions, while low-touch CS relies on automation, digital engagement, and self-service resources.

What is a hybrid Customer Success model?

A hybrid model blends high-touch and low-touch strategies, using personalized engagement for strategic or at-risk accounts, and digital automation for long-tail or healthy accounts.

How do I know which Customer Success methodology is right for my business?

Consider your customer segments, product complexity, business goals, available resources, and technology stack. 

Keeping today’s customers happy is a challenging mission. It’s not enough to have an excellent product and sell it to people who need it: organizations need to proactively address concerns, drive usage, and prove value, or they risk losing their hard-earned customers to their competition. That’s where a formal Customer Success program comes in. Done right, it can lower churn, boost product adoption, and transform happy customers into vocal brand advocates.

We’ll break down exactly how an established organization can execute a high-impact Customer Success implementation and roll out a program that leads to increased revenue, happier customers, and smoother processes.

This article will discuss:

• Why Customer Success implementation matters

• Assessing your current customer processes

• Securing buy-in & establishing your team

• Implementing key CS processes and tools

• Improving through training, execution, and iteration
  
  

Why Customer Success Implementation Matters

You’re an established company without a formal Customer Success program or function in place. Do you really need to implement one? The short answer is yes. Today’s customers demand proactive engagement that helps them achieve their goals – not just reactive support when something goes wrong. For established organizations, the stakes are even higher: processes become disconnected, teams operate in silos, and customer relationships start to rely too heavily on one individual champion instead of scalable systems.

A structured Customer Success implementation solves these challenges by:

• Driving adoption and value: Clear onboarding frameworks and ongoing Customer Success success plans help customers fully adopt your product, integrate it into their workflows, and derive value.

• Reducing churn: Proactive engagement and structured touchpoints keep customers supported and satisfied, setting the stage for easy renewal conversations. 

• Increasing expansion revenue: Expansion revenue has grown even more critical in recent years, with studies showing it’s a main driver of sustainable business growth. A well-implemented CS program identifies upsell and cross-sell opportunities.

For growth-focused organizations seeking to expand their customer revenue, a robust Customer Success program is essential. With that in mind, here are four steps you can follow for Customer Success implementation, which allows you to create a revenue-generating CS function from the ground up. 

Step 1: Assessing Your Current Customer Processes

Before implementing Customer Success, you need to establish a clear understanding of your organization's current standing.

• First, evaluate your current customer processes to identify any pain points. How is your organization currently handling tasks like onboarding, Customer Support, and renewals? 

• Also, map the entire customer journey, from sales handoff through onboarding, adoption, renewals, and advocacy. Identify how each stage is currently being managed, including the existing touchpoints.

• Collect data on churn, retention, product usage, and customer satisfaction. Look for obvious areas that need improvement. 

Your goal at this stage is to clearly define your current processes, identify gaps, and pinpoint the issues you want Customer Success to address, whether that’s reducing onboarding friction, increasing product adoption, or improving renewal rates. 

Step 2: Securing Buy-In & Establishing Your Team

Next, for your Customer Success implementation to soar, you need organizational commitment. In established companies, this likely means shifting from ad-hoc customer care to a formal, recognized function that’s backed by leadership. Data shows that only about one-third of organizational change initiatives are a clear success. For your new Customer Success implementation to stick, full buy-in is essential. 

• Begin by getting executive sponsorship. A CS program requires the visible support of the C-Suite to secure funding, gain a seat at the decision-making table, and influence strategy. To do so, position Customer Success as a revenue-driving function that’s essential to achieving business goals.

• Next, move on to cross-functional alignment. Customer Success does not function in isolation – it needs to work seamlessly with Sales, Product, Support, and Marketing. Align goals across teams, and clarify how Customer Success fits into the broader customer experience (and why it should be a priority). 

With this support, you can then formally stand up a CS team or function. Determine your structure based on your business and goals, and define team roles (such as CSMs, analysts, and ops) and responsibilities. For example:

• Customer Success Managers: Own relationship building, adoption, and retention.

• CS Operations: Processes, data, and tool management.

• CS Analysts: Track metrics and generate insights.

Nascent Customer Success teams will likely require team members to cover multiple functions and roles, but keeping in mind the various responsibilities will help you build a team that can prioritize and grow. 

Step 3: Implementing Key CS Processes and Tools

Once you have buy-in and a dedicated team, the next step is to give that team the structure and resources they need to operate efficiently. In established organizations, this often means replacing patchwork workflows with standardized, scalable processes and technology.

1. Standardize the customer journey: Create documented playbooks for all major stages. Define the cadence and format for each touchpoint, so no step is skipped or handled incorrectly. 

2. Centralize knowledge: Develop an internal knowledge base that holds guides, customer-facing templates, and escalation protocols. 

3. Select and integrate tools: Consider tech like a Customer Success platform, CRM, and engagement tools to help with workflows, data, visibility, and communications.

4. Design for growth: Even if your initial rollout is for a small set of customers, design processes that can scale across segments and geographies. 

By standardizing processes and equipping your team with a robust Customer Success tech stack, you can create a CS function that delivers a consistently excellent customer experience. 

Step 4: Improving Through Training, Execution, and Iteration

You have all the elements necessary for an all-star Customer Success implementation. Now, it’s time to ensure your team knows how to run your CS program and that it continues to improve over time. This last step gives your team the skills they need to deliver results and builds a culture of continuous improvement.

• Train for excellence: Your Customer Success team members will need training, even if they’re already experienced. Start by addressing your CS team’s skills: are there any skills gaps that need to be addressed? Then, offer targeted Customer Success enablement and training to ensure everyone has the skills they need to thrive. 

• Thoroughly onboard: Conduct employee onboarding sessions that cover the new processes and playbooks, best practices for ongoing customer engagement, and tool-specific training. Ensure that all documents are accessible in a centralized knowledge base, so CSMs know where to turn when they need to review new protocols.

• Monitor and measure: Track your results closely, using KPIs such as retention/churn rates, product adoption, net revenue retention (NRR), and customer health scores. Look for trends that align with your broader goals, such as reducing churn, achieving faster time-to-value, or increasing sales expansion.  

• Improve through interaction: Your CS program isn’t stagnant: you should treat it like a living system by regularly updating it as your product, customers, and market change. Adjust processes, playbooks, and training based on what’s achieving results, and what isn’t. 

Customer Success implementation from scratch in established organizations might seem daunting. But by assessing your current state, securing buy-in, putting the right processes and tools in place, and committing to ongoing Customer Success enablement and iteration, you can create a Customer Success function that acts as a sustainable driver of long-term business outcomes. 

Frequently Asked Questions About Customer Success Implementation in Established Organizations 

What is Customer Success implementation?

Customer Success implementation is the process of building or formalizing a structured approach to helping customers achieve their goals with your product or service. It involves setting up Customer Success processes, tools, teams, and metrics to proactively manage customer relationships, reduce churn, and drive growth.

Why is Customer Success implementation important?

Even existing companies can face issues like inconsistent onboarding, siloed customer data, or missed expansion opportunities. Customer Success ensures a consistent and proactive customer experience that improves retention, product adoption, and drives revenue growth.

What are the steps to implementing Customer Success?

Begin by auditing your current customer processes, identifying gaps, and setting measurable goals. Then, secure buy-in, align teams, create standardized processes, and equip your team with the right tools. 

Preventing customers from churning has always been important. But recently, it’s become an even greater concern for SaaS and subscription-based businesses. New customer acquisition has become more challenging, leaving retention and expansion as the main drivers of stable recurring revenue. While manual methods and ad hoc tech can help you reduce churn, there’s another option: dedicated churn prevention software.

These tools are designed to give Customer Success functions unparalleled insights into the state of their accounts. Predictive health scoring surfaces early risk, Digital Customer Success automates routine touchpoints at scale, and proven playbooks not only flag risks but also help CSMs know which next steps to take.

This article breaks down what you need to know about churn prevention software, how you can use it to drive measurable retention gains, and pragmatic implementation tips to ensure a smooth rollout.

This article will discuss:

• What exactly is churn prevention software?

• Does churn prevention software really pay off?

• What must-have features stop customers from churning?

• How to implement churn prevention software
  
  

What Exactly Is Churn Prevention Software?

The state of SaaS is changing, and acquiring new business is becoming increasingly challenging. This is due to a few reasons: 

• There’s increasing business competition in the fast-growing SaaS space, which is due to grow in value by the hundreds of billions in the next few years alone. 

• Customer expectations are rising, with more than 50% of customers saying they’ll switch to a competitor after a single unsatisfactory customer experience. 

• Fluctuating market conditions and challenging economic times are leading to slimmer budgets and recession fears, causing companies to be more hesitant to buy and more critical when they do.

This has led to an ecosystem where churn prevention is a main priority, and retention is critical for long-term business success. While many Customer Success processes and systems can help reduce churn, churn prevention software has emerged as an effective, cutting-edge solution.

What is churn prevention software? It’s Customer Success technology that ingests signals which indicate if customers are likely to churn, predicts risk, and orchestrates the right interventions (some automated, some human). Think of it as a purpose-built layer that sits between your product, data sources, and messaging channels to continuously answer three questions:

• “Who is at risk?”

• “Why are they at risk?”

• “What should we do?”

Churn prevention software is distinct from other Customer Success tools. For example, CRMs track relationships and deals, but aren’t designed to compute health shifts or launch playbooks at scale. Or consider product analytics, which explain what users do in-app, but rarely connect to CSM workflows or trigger multi-channel interventions.

Does Churn Prevention Software Really Pay Off?

Churn prevention software can be a powerful retention differentiator, arming your CS team with early warning systems and automation tools that allow them to identify and prevent churn at scale. So, for most organizations, the question isn’t whether churn prevention software pays off—it’s how quickly and measurably it does. 

Direct ROI: Retention, Expansion, and Efficiency

Organizations that invest in the right churn prevention software typically see direct measurable results like:

• Retention: Early detection of risk leads to more timely interventions and fewer lost accounts.

• Expansion: Healthier customers are more likely not only to renew, but also expand their licenses and upgrade products.

• Efficiency: Automation and Digital Customer Success capabilities enable teams to act at scale, expanding outreach and engagement without necessitating headcount growth. 

The benefits compound: when at-risk customers are saved, renewal revenue stabilizes, and Customer Success teams can focus on identifying expansion opportunities.

Indirect ROI: Confidence and Alignment

The payoff of this tech isn’t purely financial. Churn prevention tools also give CSMs the clarity and support they need to act with confidence. Instead of relying on gut feeling or anecdotal evidence, they can prioritize accounts based on data and concrete signals. Then, playbooks and automation reduce guesswork, ensuring consistent customer experiences across the board.

This alignment can reduce CSM stress, improve morale, and elevate Customer Success from a reactive support function to a strategic driver of growth.

Ultimately, churn prevention software helps turn Customer Success into a continuous improvement function. Instead of reacting to churn when it’s too late, CS builds scalable systems for adoption, retention, and expansion.

The one thing to keep in mind? Not all of this software is created equal, and for it to work, it must have the right features.

What Must-Have Features Stop Customers From Churning?

If you want to deploy a platform in your org that will actually reduce churn, here are the key features it should include. While your chosen solution may not have every feature, you can select the ones that will make the biggest impact on your Customer Success function and business goals.

1.  Predictive Health Scoring

What it is: A composite score calculated by blending product usage, customer behavior, support sentiment, and other signals to forecast churn risk. By integrating predictive analytics, these scores alert CSMs to early warning signs such as drops in login frequency, declining feature adoption, or shifts in support ticket sentiment.

Why it matters: If you can't predict risk early or understand that it's happening, you can't get ahead of it. Reactive responses to churn are typically too late; by the time a customer explicitly signals their intent to leave, you've already lost the relationship. Predictive health scoring gives your team a head start on intervention.

What it should look like:

• Transparent score factors and drivers (e.g., "Admin log-ins down 32%, license usage 54%, support sentiment negative").

• Segment-specific models (SMB vs. Enterprise, new vs. mature accounts, different product tiers) with clear thresholds that define what constitutes "at-risk" for different customer segments.

• Real-time alerts for sudden deviations from normal trends, with severity levels that prioritize CSM attention.

• Historical trending that indicates whether health is improving, declining, or stable.

What to avoid: Opaque scores where CSMs can't understand what's driving the risk, one-size-fits-all thresholds that don't account for segment differences, or scores that update so infrequently that the data is stale by the time CSMs can act.

2. Automation & Digital Customer Success Tools

What it is: Task and touchpoint automation, checklists, behavior-triggered communications, and in-app guides that allow CSMs to scale timely, personal engagement. These tools enable proactive outreach at critical moments, without requiring manual CSM intervention for every customer.

Why it matters: Churn prevention requires consistent, timely engagement at scale. Automation ensures every customer receives relevant nudges at the right moment without overwhelming the CSM or sending non-specific information. 

What it should look like:

• Behavior-triggered communications (onboarding stalls, feature non-usage, approaching renewal, license utilization thresholds).

• Personalization by role, lifecycle stage, industry segment, and company size.

• In-app guidance that surfaces contextually based on user actions and needs.

• Guardrails to prevent over-communication and ensure messages remain relevant 

• Integration with CSM workflows so that automation complements rather than replaces human touch.

What to avoid: Batch-and-blast campaigns with no link to health or risk status, generic messages that don't reflect customer context, automation that creates "noise" rather than value, or systems that operate independently from CSM workflows, creating disconnected customer experiences.

3. Actionable Insights & Playbooks

What it is: Churn prevention software shouldn't stop at flagging risk—it should guide CSMs on what to do next. The best platforms embed specific actions or entire playbooks with clear owners, steps, and assets directly within the alert workflow.

Why it matters: Risk alerts without recommended next steps create two problems: they overwhelm CSMs with "alert fatigue," and they leave teams guessing about the right response. When the platform suggests concrete next steps, CSMs can act immediately and consistently.

Beyond individual alerts, effective churn prevention software should also surface patterns across your customer base. When multiple accounts share common warning signs, the system should identify these trends and enable you to deploy targeted playbooks at scale.

What it should look like:

• Playbooks tied to specific triggers (usage dips, support sentiment spikes, champion turnover).

• Built-in tasks, timelines, stakeholder maps.

• Pattern recognition that groups similar risk profiles for at-scale interventions.

What to avoid: Generic “reach out” suggestions and no measurement of intervention impact.

4. Churn Reasons & Outcome Attribution

What it is: A standardized taxonomy for documenting why customers churn and which interventions successfully prevented or addressed churn risks. The system should track both the root causes of churn and the specific actions taken to address them, creating a clear line of attribution between CS activities and revenue outcomes.

Why it matters: Without systematic churn reason tracking, organizations can't identify patterns or address systemic issues. More importantly, without attribution to CS interventions, teams struggle to demonstrate their revenue impact to leadership. You can't fix what you can't name, and you can't prove impact without clear causation between your actions and outcomes.

What it should look like:

• Consistent root-cause categories aligned to your business (pricing concerns, product gaps, adoption challenges, support issues, champion turnover, competitive replacement).

• Attribution model connecting specific CS interventions to saved or expanded revenue.

• Outcome tracking that distinguishes between churns prevented, renewals secured, and expansions influenced by CS activities.

• Integration with health scoring so you can correlate early warning signals with eventual outcomes.

What to avoid: Vague categories like "other" or "unknown" that obscure patterns, no connection between interventions and results, or systems that track churn reasons but not the effectiveness of responses. 

5. Integrations & Data Foundations

What it is: Connections to all relevant data sources that influence customer health: product analytics and usage events, CRM relationship data, billing and subscription information, support ticket systems, NPS and survey feedback, contract details, and user identity and role information. These integrations create a unified view of each customer's journey and current state.

Why it matters: Data accuracy and freshness determine signal quality. A health score based on old usage data misses critical changes in customer behavior. Disconnected systems force CSMs to manually piece together the customer story from multiple sources, increasing the risk that important signals get missed.

What it should look like:

• Daily (or better) data refreshes from all connected systems.

• Role-level targeting that understands not just company usage, but which specific users and roles are engaging.

• A unified customer record that eliminates conflicts between different system data.

What to avoid: Stale usage data that's only refreshed weekly or monthly, heavy reliance on manual CSV uploads that create data gaps, or systems that can't trigger actions in other platforms (like creating CRM tasks or sending targeted emails).

6. Segmentation & Personalization

What it is: Dynamic audience groups used to tailor engagement strategies and prevent churn at scale. Segments might be defined by ARR tier, industry vertical, product edition, lifecycle stage, geographic region, or even behavioral patterns like "power users" versus "struggling adopters." These segments enable different health thresholds, playbooks, content, and engagement models for different customer types.

Why it matters: Relevance drives engagement and adoption, which therefore reduces churn. Personalization by segment ensures every customer receives engagement appropriate to their context, increasing both efficiency and effectiveness.

What it should look like:

• Multi-dimensional customer segmentation beyond just company size 

• Content variations tailored to each segment

• Segment-specific health score thresholds that account for different "normal" patterns.

• Reporting by segment to identify which customer types are succeeding versus struggling.

What to avoid: One journey for all customers regardless of their needs or context, segments so granular they become impossible to manage effectively, or segmentation that exists in theory but isn't actually applied to personalize the customers’ experience.

7. Reporting & Executive Dashboards

What it is: A consolidated view of customer health trends, risk distribution, intervention effectiveness, and business outcomes that connects churn prevention activities directly to revenue impact. These dashboards reveal not only which customers are at risk but also what actions are being taken, which playbooks are effective, and how CS activities translate to preserved and expanded revenue.

Why it matters: Customer Success leaders need to quickly identify which customers are struggling, understand why, and determine the appropriate actions to take. More importantly, they need to demonstrate to executive leadership that CS activities directly drive business outcomes. Without clear reporting that connects effort to impact, CS remains perceived as a cost center rather than a revenue driver.

What it should look like:

• Executive-level metrics that connect to revenue (NRR, GRR, churn rate, expansion rate, saved revenue).

• Clear visualization of risk distribution across the portfolio with drill-down capability.

• Trend analysis that identifies whether overall customer health is improving or declining.

• Outcome attribution that quantifies CS contribution to specific revenue results.

What to avoid: Over-reliance on vanity metrics (like number of touchpoints or emails sent) without links to churn reduction, complex reports, or dashboards that only show lagging indicators.

How to Implement Churn Prevention Software

After choosing a churn prevention software for your business, you’ll want to make sure the deployment is a success and that your team fully adopts it. Instead of simply launching your solution and hoping for the best, here are best practices you can use to ensure your rollout is fast, focused, and effective:

I. Foundation & Planning (Strategic Setup)

Start with desired outcomes, not features. Before jumping into your new software solution, clarify the business outcomes you expect to see from the program, such as a 20% reduction in ARR at risk in two quarters. Map each outcome to the signals, playbooks, and reports required to prove movement. This ensures all users are aligned on how to make the most of your new solution, while preventing tool "bloat" (such as nice-to-have dashboards that nobody uses).

Segment customers for tailored insights. Churn risk manifests differently across customer segments. Segment your customers based on criteria like industry, usage patterns, and account size to ensure that your churn prevention efforts are personalized. Create targeted strategies for high-risk segments, such as offering specialized retention offers or addressing product gaps.

Plan how it will integrate with the existing tech stack. Churn prevention software should work seamlessly with other systems in your tech stack, like your CRM, support tools, analytics platforms, and comms systems. Proper integration allows for a unified view of the customer journey and ensures no valuable data gets lost in the process.

2. Technical Deployment (Systems & Data)

Set up automated alerts and triggers. Automation is your ally in churn prevention. Set up automated alerts for key churn indicators, such as decreased product usage, unresolved support tickets, or negative feedback surveys. When your team gets automatic alerts, they can immediately address at-risk accounts so nothing slips through the cracks.

Ensure proper data connections and refresh schedules. Data accuracy and freshness determine signal quality. Configure daily (or real-time) data refreshes from all connected systems to ensure health scores reflect current customer behavior rather than stale information. 

Embed Digital CS for scale. Support your CSMs with Digital Customer Success churn reduction techniques to address churn at scale. For example, incorporate feature activation nudges when a high-value feature is unused by a certain day, or a pre-renewal health warm-up sequence, tailored by stakeholder role.

3. Adoption & Change Management (People & Process)

Invest in training. Platform training shouldn't be a single demo followed by "good luck." Implement a progressive learning approach: foundational training on navigation and core features, role-based sessions showing how the platform fits specific workflows, and advanced training on sophisticated features.

Operationalize response playbooks. What do Customer Success Managers do when they see that a customer is at increased risk of churn due to decreased product usage? That's something leaders need to decide on. Every alert type should route to a playbook that gives CSMs clear steps, talk tracks, and assets to help reverse the churn risk. Even if your platform has built-in suggestions, CSMs still need to know what internal protocols to follow.

Establish accountability and track adoption metrics. Define specific adoption milestones: week one goals might include updating all assigned account health scores, week two could require launching the first automated playbook, and week three might focus on documenting the first churn reason with attribution. Track platform usage metrics and address low adoption early. Make it clear that updating health scores, executing playbooks, and documenting outcomes are core job responsibilities.

4. Ongoing Operations

Ensure cross-department collaboration. Churn prevention doesn't rest solely on the shoulders of Customer Success: it requires input from other departments, like Sales, Marketing, and Product. Ensure that the insights gained from churn prevention software are communicated across departments. This collaboration ensures that all teams are aligned on customer needs, potential issues, and the right strategies to prevent and reduce churn.

Monitor usage and iterate. Track both platform adoption metrics and business outcomes. Are CSMs logging in regularly? Are playbooks being completed? Most importantly, are at-risk customers being saved? Create an adoption dashboard that shows both individual and team utilization, and connect platform usage to actual retention improvements to demonstrate value. 

Continuously refine your approach. Health scoring models, triggers, and actions will need adjustment over time. You can't just set it and forget it. Schedule regular reviews to evaluate what's working: Are certain triggers generating too many false positives? Are specific playbooks consistently reversing risk while others fall flat? Use data and CSM feedback to refine your models. Churn prevention software is a system that evolves with your business, customer behavior, and market conditions.

Churn prevention software can be powerful, but it has to have the right features and be thoughtfully deployed. Choose a software that has features such as predictive health scoring, digital Customer Success features, actionable playbooks, segmentation, and churn attribution. Then, make sure your people and processes are up to speed. When you anchor on outcomes, operationalize your playbooks, and work cross-functionally, you build a repeatable system that reduces risk, accelerates adoption, and compounds NRR.

Frequently Asked Questions About Churn Prevention Software

1. What is churn prevention software?

Churn prevention software is a Customer Success platform that aggregates customer data from multiple sources (product usage, CRM, support, billing, surveys) to predict churn risk, trigger alerts, and guide CSM interventions before customers leave.

2. How does churn prevention software work?

The software ingests data signals to calculate customer health scores. When scores drop below defined thresholds, the software sends risk alerts and routes playbooks with specific next steps to CSMs to help reverse the churn risk. 

3. What are the must-have features of churn prevention software?

Churn prevention software should have features like:

• Predictive health scoring (segment-specific models)

• Automated alerts and task routing

• Actionable playbooks with clear steps and assets

• Digital CS capabilities (in-app guides, automated journeys)

• Integrations with CRM, product analytics, billing, and support systems

• Churn reason tracking and outcome attribution

4. How do you implement churn prevention software?

Start with clear business outcomes rather than features. Segment customers for personalized insights, integrate with your existing tech stack, set up automated alerts, and invest in comprehensive CSM training. Establish accountability metrics and plan for ongoing iteration as you learn what works.

5. Does churn prevention software replace Customer Success Managers?

No. Churn prevention software enhances CSM effectiveness by providing early warning signals and scaling routine touchpoints, but human judgment and the personal touch remain critical for complex interventions, relationship building, and strategic account management. 

When you’re part of a subscription-based business, you’re almost always on your toes, either trying to encourage retention, spot risk, or prevent churn. Even “smooth sailing” customers require work from Customer Success Managers, particularly when it comes to customer renewals. The perfect scenario is when happy customers simply renew on their own accord. But in some cases, CSMs end up doing last-minute fire drills to encourage accounts to extend their contract. The result: discount leakage, slipped dates, and avoidable churn. However, with the right customer renewal strategy, CSMs can strategically encourage renewals at scale.

This article will discuss: 

• What should CSMs know about the renewal landscape today?

• Why do customer renewal strategies matter for CSMs?

• Five reminders for driving smooth, consistent renewals 
  
  

What Should CSMs Know About the Renewal Landscape Today?

Customer renewals are a significant part of the SaaS lifecycle, and for seasoned Customer Success Managers, they’re nothing new. But recently, renewals have become even more mission-critical to secure. The state of SaaS has shifted in recent years, and acquiring new customers has grown more challenging. Research shows that long-term, sustainable business growth is now rooted in retention and expansion.

Another factor impacting renewals? Competition. The SaaS market is expected to increase in value by more than $50 billion in the next year alone, and by hundreds of billions in the next few years. This means that there will be more solutions coming to market, more quickly, offering customers alternative options that are highly competitive. Translation? Even happy customers can be tempted to churn. 

Recent data from ChurnZero shows that there is also good news on the horizon: retention has stabilized after years of decline. This means that in many cases, Customer Success functions can switch from a reactive, red-alert strategy to a proactive, offensive strategy. This can include a systemic, targeted customer renewal system. 

Why Do Customer Renewal Strategies Matter for CSMs?

Customer renewals come up on their own, whether Customer Success Managers approach them proactively or not. With satisfied customers, renewals can be a breeze and often take care of themselves. But in many other cases, the following scenario can happen: a busy CSM puts renewal efforts at the bottom of the to-do list, and in the 11th hour, a customer who appeared happy announces they’re churning.

Here’s why a customer renewal strategy can make all the difference:

• Prevent last-minute surprises: A long-term renewal strategy allows CSMs to gauge customer sentiment and address issues early, avoiding rushed renewal efforts when it’s already too late.

• Leverage customer insights: CSMs have direct visibility into valuable customer data, such as goals and product usage. These insights can inform renewal efforts and help CSMs deploy tactics designed for individual customers.

• Enable growth opportunities: Smooth renewals can lead to even more revenue. When customers are ready to sign on for another term of service, they might also be well-positioned for expansion, like upsells or cross-sells.

• Reduce churn risk: Monitoring customer health throughout the lifecycle helps CSMs identify risks long before renewal time.
  
  

Five Reminders for Driving Smooth, Consistent Renewals

Customer renewals shouldn’t be a last-minute scramble. When executed well, they’re the natural outcome of sustained value realization, clear communication, and a strong customer relationship. To improve your approach, here are some reminders that can help you ensure renewals are predictable and effortless.

1. Relationships Heavily Influence Renewals

Sure, product value, usage, and pricing are core elements of renewals. But the relationship between a CSM and their customer also plays a big role in whether someone stays on board or not. Data shows that nearly 90% of customers will keep doing business with a brand when they have a connection with a customer service agent. When CSMs nurture customer relationships, renewals are a natural byproduct. This doesn’t necessarily mean you need a personal, high-touch relationship with every customer, but it is important that they feel a connection with your brand and organization. If they only hear from you at renewal time, it’s likely they don’t feel that connection. Even strategically automated messages and touch points can help build a relationship. 

2. Timing is Everything (and You Can Plan around it)

Renewal conversations can be tricky. Bring them up too soon, and it’s not relevant. Bring them up too late, customers will have already made up their minds. How can you know where the sweet spot is? Here are some timing factors to keep in mind:

• Back-plan from the renewal date: Depending on the size of the business you’re working with, you might start your renewal motion 60 days in advance, 90 days, or even more. A good rule of thumb is that complex enterprise solutions will need longer renewal processes, while SMBs and simple clients can be approached with a shorter motion.

• Respect your customer’s calendar: Keeping events in mind like your customer’s fiscal calendar, board meetings, and even holidays can make a difference in your strategy – and the results.

• Quarter ends create drag: Avoid introducing initial renewal conversations too close to the end of the quarter. Your champion may be consumed by their own QBRs and revenue close.
  
  

3. Not all Renewals are Equal

Renewals can vary significantly in complexity. For example: 

• Low-touch: Simple auto-renewals for smaller, satisfied accounts.

• Mid-touch: Renewals that require some check-ins and minor negotiations.

• High-touch: Strategic renewals involving multiple stakeholders, custom pricing, or legal reviews. 

CSMs should understand what category each customer falls into and tailor their approach accordingly. 

4. Keep Key Data at Your Fingertips

Data is a CSM's best friend and can be a major asset for customer renewals. Here are some key metrics to monitor, which can help shape your renewal strategy:

• General account data: Basic account insights like term dates, customer segment, and ARR.

• Adoption & usage: Seats purchased vs. active, feature deployment, and weekly active users. 

• Outcome proof: A customer’s baseline metrics vs. current state, and the subsequent impact (time saved, cost avoided, or risk reduced).

These insights can help you make a business case for renewal, demonstrate the value of your solution, or highlight areas where your product can drive even further positive results. 

5. Take Steps to Reverse Risk in Advance

Low product adoption, infrequent communication, and unresolved support tickets signal that a customer may not be well-positioned for a renewal. The goal of CSMs is to spot risk early, document it, and act on it systematically. If you see a customer’s adoption is starting to slip, don’t just plow ahead with your renewal sequence. Instead, start an enablement sprint well in advance to first drive better adoption. Interventions of this type set the groundwork for a successful renewal. 

Customer renewals can’t rely on luck, and they don’t have to be a mad dash. By understanding the state of renewals today, clarifying why renewal strategies matter, and keeping certain best practices in mind, Customer Success Managers can turn renewals from a gamble into a surefire bet. 

Frequently Asked Questions About Customer Renewal Strategies 

1. What is a customer renewal strategy?

A customer renewal strategy is a structured, proactive approach to securing contract extensions with existing customers.

2. What should Customer Success Managers know about renewals?

Customer renewals are critical for ensuring long-term, sustainable business growth. They also shouldn’t be reactive or left up to chance. Instead, CSMs can deploy strategies so that renewals are predictable.

3. How can Customer Success Managers drive consistent renewals?

Remember, relationships heavily influence renewals, and customers are often more willing to continue doing business when they have a strong relationship with a rep. Timing is also important to keep in mind: consider events like your client’s fiscal calendar. Next, categorize renewals by their complexity. Large accounts require a high-touch approach, while SMBs can likely be automated. Lastly, use data to inform your renewal approach. Account, adoption, and outcome data can inform your renewal approach.

2025 Customer Success Thought Leadership Awards: Recognizing the CS Professionals Shaping Our Industry

We're excited to announce the winners of the 2025 Customer Success Thought Leadership Awards: the Top 25 Customer Success Influencers and Top 100 Customer Success Strategists who are advancing our profession through exceptional thought leadership, mentorship, and meaningful community contribution.

Why These Awards Matter

The Customer Success Thought Leadership Awards serve a critical purpose beyond recognition. They help connect the community with the voices actively shaping our profession.

These award recipients aren't just exceptional practitioners; they're the professionals who:

• Share insights that change how we approach Customer Success

• Mentor others through guidance, coaching, and educational contributions

• Build connections and foster collaboration across the CS community

• Drive important conversations that advance industry standards and practices

By highlighting these CS pros, we create opportunities for the wider Customer Success community to discover, connect with, and learn from professionals who are actively advancing the field. Whether you're a seasoned CS executive or just starting your career, following these thought leaders provides access to the strategic thinking and innovative approaches that are defining the future of Customer Success.

Meet the 2025 Winners

Top 25 Customer Success Influencers

These 25 influencers are selected by our expert judging panel based on their impact. These CS pros have shaped industry conversations, advanced CS practices, and contributed to community development through thought leadership and mentorship. Their influence extends across the Customer Success field, driving positive change and elevating standards for the entire profession.

Top 100 Customer Success Strategists

These 100 strategists were chosen by CS professionals worldwide through direct voting. They demonstrate excellence in thought leadership, mentorship, and collaboration, advancing the profession through their knowledge sharing, guidance, and active participation in elevating Customer Success practices. Their strategic insights have resonated across the field, making them valuable resources for anyone looking to strengthen their CS approach.

Thank You to Our 2025 Judging Panel

The Top 25 Customer Success Influencers were selected by a distinguished panel of industry judges who brought expertise, care, and thoughtful evaluation to the process. Each judge has been previously recognized as a Customer Success Thought Leadership Award winner, and they volunteered their time to identify this year's most influential voices.

Join Us in Celebrating Excellence

The 2025 award recipients represent the voices shaping Customer Success right now. Take a moment to discover the CS professionals who are making the biggest impact in 2025, and connect with their work to become part of the collective effort to raise standards and advance Customer Success practice.

We encourage you to:

• Explore the winner lists and identify professionals whose expertise aligns with your CS challenges and interests

• Follow the winners on LinkedIn to benefit from their insights, frameworks, and strategic thinking in your feed

• Engage with their content by commenting on posts, attending their webinars, and participating in discussions they lead

• Share their work with your teams and networks to amplify valuable CS insights across the community

Congratulations to all 2025 Customer Success Thought Leadership Award winners. Your contributions matter, and the community has spoken: you're making a difference.

CS Leadership Roundtable #58 Transcript: Managing Change and Uncertainty in Customer Success

Organizational change and shifting market conditions are inevitable. For Customer Success professionals, these changes can directly impact processes, priorities, and customer relationships. Whether it’s adapting to a new leadership vision, supporting customers through product pivots, or responding to industry disruptions, the ability to remain flexible and effective is critical to long-term success. Without the right mindset and tools, change can feel disruptive, impacting both performance and customer trust.

This webcast will provide strategies for navigating change with confidence and resilience. By understanding the dynamics of change management, CSMs will not only survive periods of uncertainty but also position themselves as a trusted partner to both their company and their customers.

During the live CS Leadership Roundtable, the panelists discussed:

• Common challenges when adapting to organizational or market changes

• Communication strategies for keeping customers informed

• The role mindset plays in successfully adapting to change

• Proactively anticipating customer concerns during periods of transition

• Balancing new internal priorities with ongoing commitments to customers

• Skills or habits that help CSMs remain resilient in fast-changing environments

For this CS Leadership Roundtable event, host Andrew Marks was joined by:

• David Karp, Chief Customer Officer at DISQO

• Lorenzo Serva, Senior Manager, Customer Success at Dynatrace

• Toby Lucich, COO, Founder at Magic Button Labs

Top Takeaways 

1. Build teams that thrive in uncertainty rather than shield themselves from it. When organizations prioritize stability during periods of change, they face failure rates of 60 to 70 percent. In contrast, highly successful CS teams anticipate, adapt to, and even initiate change. By shifting from a protective mindset to one that embraces adaptability, teams can build the resilience necessary to effectively serve customers, even amidst change.

2. Distribute decision-making power to those closest to the work. Push decisions to team members who best understand market context and customer needs. This builds organizational resilience and frees leaders to focus on strategic direction, but it requires trust, not control.

3. Communicate transparently about what you know and what you don't. Only 19 percent of employees trust their CEO to tell the truth, yet admitting uncertainty builds far more credibility than carefully crafted messaging. When leaders acknowledge what is unclear while maintaining direction, teams become more adaptable rather than anxious.

4. Involve your team in designing the change, not just implementing it. Employees who co-create change initiatives show 79th percentile engagement compared to 24th percentile for those who feel disempowered. Inviting your team to shape solutions turns resistance into ownership and leads to faster, more effective outcomes.

5. Apply the same change enablement principles to your customers that you use internally. Your role as a vendor is not to drive change for customers but to equip them to drive it themselves through toolkits, frameworks, and examples. When customers can explain the change in their own words using your language, you have successfully transferred ownership and reduced implementation friction.

6. When new responsibilities arise, negotiate capacity boundaries. Map your team’s critical path to customer value and use it to guide tradeoffs when new initiatives appear. Leaders who say "yes, and here is what we will need to stop doing" prevent burnout while keeping focus on what truly drives success.

Session Replay

Session Transcript

NOTE: The following transcript has been edited for clarity and content where necessary to improve readability.

Andrew Marks: So welcome everybody to the CS Leadership Roundtable, your monthly forum for actionable insights across Customer Success, support, and service. I'm Andrew Marks, Co-founder and Architect of the SuccessCOACHING Training Program, HOA President in my local HOA community. And I'm thrilled to be leading today's conversation on managing internal change in uncertainty. This learning series is brought to you by SuccessCOACHING where we've trained over 40,000 professionals across 96 countries. Whether you're focused on Customer Success, Technical Support, or Frontline Service, our programs are designed to help your team deliver exceptional customer experiences. You can find out all of the details of our offerings on our website, successcoaching.co, or in the chat where Ashli has provided some links and any coupon codes that we're offering. Also, make sure to check out our new Value-Based Selling Program designed to transform how customer-facing teams engage accounts shifting from transactional conversations to strategic outcome-focused partnerships.

Just a little housekeeping, a few quick housekeeping notes. This session is being recorded and will be available next week with a transcript. Use the Q&A button for questions. Higher upvoted questions get priority. And please keep the chat for commentary only. So questions in Q&A, commentary in chat. LinkedIn live viewers can post questions directly in the comments which will be relayed to us. Now, what sets our roundtable apart is our focus on real-world applications. We bring together industry experts who share practical insights that you can implement regardless of your company size or customer engagement model. Today I have three outstanding leaders joining me and I'm going to let them introduce themselves to y'all and have them talk a bit about themselves before we get started. So let's begin with introductions in alphabetical order with David.

David Karp: Oh, thank you, Andrew. Great to be here. I am a recovering former member of my neighborhood's HOA for sure, just here north of Dallas, Texas. Currently Chief Customer Officer at a tech company called DISQO, been here for over four years. I've spent quite a few decades in the world of Customer Success, post-sale, account management, really just delivering software technology services to companies around the world. So the other important things to know about me, been married for over 36 years, which probably says a lot more about my wife's resilience and patience than it'll ever say about me.

Andrew Marks: I was going to say.

David Karp: And so, yeah, that's me.

Andrew Marks: And I would like to compliment you on your taste of '70s garb having hung out with you at the Casino Night at CS100. In particular, the fro that you were wearing that will match up with mine.

David Karp: We were fro brothers. That was a throwback to back when I had hair.

Andrew Marks: Yes, exactly. See, there you go. I'm with you.

David Karp: A little walk down memory lane. So I try to tell people this is my middle-aged man haircut. I ask them to cut my hair this way or else I just look too young.

Andrew Marks: Yeah, that's it. Yeah, and you don't look too young. Thanks ,David. Next up is Lorenzo joining us from halfway around the world?

Lorenzo Serva: Yeah, excuse myself from the headline conversation for tonight. My name is Lorenzo Serva. I'm usually broadcasting from Sydney, Australia, that's where I'm based. But today I'm from Singapore, so it's about to be 2: 00 AM here. I work for an American company called Dynatrace, where I manage the Asia-Pacific Customer Success Team with a focus on South East Asia, China and Japan. That comes with some traveling. That's why I'm here in Singapore. It's hot and humid like you expect from here. And yeah, very excited to be here. Thanks for inviting and really looking forward to the conversation.

Andrew Marks: It's always great to have you on this Lorenzo. And we very much appreciate you getting up early for us. Hopefully it's worth the time. And last but not least, one of our longest-term, longest-serving strategic partners to the SuccessCOACHING Team. We met Toby, what? Seven, eight years ago?

Toby Lucich: Yeah, Pre-COVID, whatever that was, decade or two ago?

Andrew Marks: Yeah, I'm glad we got a chance to have some face-to-face time just back in, when was that? April when I came up with my daughter at Lincoln Colleges.

Toby Lucich: That's right.

Andrew Marks: Yeah. Awesome.

Toby Lucich: Break some bread in the spring.

Andrew Marks: Yeah.

Toby Lucich: I'm Toby Lucich with Return Leverage. I've been a Management Consultant and often an interim Chief of Staff to executives from startups to Fortune 500 simply because some initiatives are too big on top of that already large plate. So coming in to lend a hand on things from acquisition integration, to org design or strategy shifts or technology deployments, which feels like we're all going through at a near daily pace. I've been partnering with, as Andrew noted, with the SuccessCOACHING Team for, I think, about seven or eight years now. And doing a Project mManagement and Change Management bootcamps. And so, as we get into this today, happy to share some of the research that typically goes into those where it's appropriate, but always glad to join leaders that are actively in the field and tackling these topics together. So happy to be here.

Andrew Marks: Awesome, thanks Toby. And as usual, thank you for making the time and thanks all you guys for making the time and being part of this. So let's get to the topic in hand. I want to share some data that might surprise you. Surprised me. Despite decades of change management expertise, 70% of change initiatives still fail and 71% of employees report feeling overwhelmed by workplace change. We're putting enormous effort into protecting our teams, yet 37% feel less trust toward their employers after experiencing our managed changes. And change fatigue employees report higher stress and lower job satisfaction. Meanwhile, the data shows something interesting. Employees who feel empowered rank at the 79th percentile for engagement while those feeling disempowered rank at the 24th percentile. And 64% of employees say they already have the skills needed to adapt to change successfully. I think these numbers are telling us something important, something that might challenge how we think about our role as leaders.

So I'd like to start with a thought that might be a little uncomfortable for some. Maybe we've been approaching change in the wrong way. Usually we're told that change is disruptive and difficult. As leaders, we often feel it's our job to carefully manage change, guiding our teams smoothly through it, shielding them from uncertainty and creating a sense of stability and calm. We attend workshops on change management and roll out communication plans trying to make the process as painless as possible. But what if all of that, this protective and controlling approach is actually part of the problem? What if treating change as something dangerous that needs to be managed is actually making us more fragile? Think about it. The market doesn't pause for our change plans. Customers don't wait for us to finish internal transitions. Competitors keep moving forward regardless, yet we often put a lot of effort into controlling, smoothing, and slowing down change for our teams.

Interestingly, the most successful customer service organizations aren't necessarily the ones that are best at managing change. They're the ones that build teams who expect change, adapt to it, and sometimes even create it. So maybe the real question isn't how we protect our teams from change, it's why we're building teams that need so much protection in the first place. Our focus on stability and predictability might be making our teams and ourselves less resilient, not more. So today I want to challenge the usual approach. Let's think about whether we're over-managing and under-trusting. Are our change frameworks solving the right problems and could the best way to lead through uncertainty be quite different from what we've traditionally been taught? So my opening question to my panelists, let's be honest, do you feel your team is more vulnerable because you've tried to shield them from change or more tough and adaptable because of it? And really how much of your change management comes from your own discomfort with uncertainty rather than your team's capacity to handle it?

Toby Lucich: Andrew, the first response that comes to mind is that I think in general a lot of us are feeling more vulnerable at large. And I'm saying that we have to think about these as collections of individuals who have a life outside of our workplace first, and we often lose sight of that. So the economy, we all have a friend or a past colleague that's searching for jobs. I think that's been increasing and that just creates a very different tenor in the workplace. And so this idea of adaptable, I think is one of those pieces where we need to be cognizant about where people are at as they're showing up to the workplace and what we're doing to actually get them more emotionally engaged. I do think adaptability though is a learned skill. And so, as we talk more about frameworks or tools over the next hour, I think I will personally probably point to some of those things as not a panacea, not a magic silver bullet, but a way to help folks cultivate that adaptability muscle.

David Karp: Yeah. If I can add to that a little bit, I think that's really, really well said, Toby. I think what's really interesting now is not just the fact that we have to think differently about change. It's the pace of change, the expectation of change, all of that is accelerated, whether it's driven by AI, it's driven by change in capital markets. Where I found myself doing a disservice to the team at times is being more concerned about how they can handle the pace of change than making sure that they're set up to hear the change that's coming be part of driving the process for change so they're active participants. And letting that help us determine who's in for the change, who's adaptable, and who's not.

It's really to me, the amount and pace of change. And if I try to use my old school, we'll go through it, I'll slow it down. The next change will already be on top of us before we've worked through the last one because it's coming all the time. I can't manage it. And so whether or not I'm comfortable shouldn't be the gating factor. It should simply be that as a leader, my job is to create the opportunity for the team to engage in that change at that pace, period.

Lorenzo Serva: Love your point, David, totally resonate with me. And for me there's an additional dimension that comes with managing in a diverse across different cultures and geos. So yes, it's about creating that framework for execution and keeping the pace through change, but also to push the decision and the actual activity down to a layer of the organization where they know how to execute in that market, in that framework. And I don't know, I need to push decision down to a point where I can trust the organization to be effective in that context. So that makes this funny dynamic because that makes the team more resilient but takes away power for me because I need to trust the team more than I would've otherwise. So I might feel more fragile, but that is the measure for me to know that the team is operating at the best.

Andrew Marks: And that's an interesting segue to another piece of data that I found from a Gallup poll this year. 72% of leaders feel used up at the end of the day, that's a 12% increase from 2020. And manager engagement dropped from 30% to 27% in 2024. That's the sharpest decline of any group. Since 70% of team engagement is attributable to the manager that leaders' own struggles with change significantly impact their teams. So it's not just the individual contributors, it's leaders, they're exhausted. And only 17% of executives feel capable of executing transformational plans. 50% can't confidently assess if recent changes succeeded. It just seems like with all of this, and Toby, I know you are a master practitioner of change management. What do you think about those statistics? It's almost like even with all of the training that we offer and all the frameworks and everything, it's just it's still tough.

Toby Lucich: 100%, Andrew. I think the job of being a leader today is much larger and more complex than it was even 10 years ago. David touched on some of the externalities we balance, what are the capital markets doing? What are investors expecting? We also have this new AI thing that feels like it's a magic silver bullet for everything, but we're still learning how to use it and we don't know when it's going to misfire. And that's a little bit tricky too. And so the Gallup poll statistic that sticks in my mind is that one in five of our employees is actively disengaged, meaning they're not just mailing it in, they show up to work for sport and trying to figure out how to make it entertaining. And it's usually not advancing our agenda.

So when we start to talk about the never-ending cascade of changes, we're kind of in a sea and it's rocky right now and it's not going to calm down anytime soon. Based on conversations with clients and teams. So this idea of how fast is it changing and are we managing it, I think what we're best capable of doing is figuring out to Lorenzo's point, where do we give away some of our power? How do we distribute that power to build a stronger team of equals as we try to navigate this together, because we simply can't be everywhere all at once.

Andrew Marks: Well, and something that David and I were talking about before you guys jumped on as well is in Customer Success, in customer-facing roles, change is the only constant. So you have to be willing and able to adapt. So it begs the question, do we have the right people on the team? So that leads into my next question, which is I want you to think about someone on your team who's really struggled with change versus somebody who's thrived. What's actually different about them? Is that one needed more management of the change or is it something else entirely? Maybe their fundamental relationship with uncertainty? I don't know, what is it? Anybody have an example?

David Karp: If I can, and I'll put it in maybe back in the context of mindset. And if I can a little story from one of my favorite movies, a movie called Parenthood, if anybody's seen it with Steve Martin. There's a great scene where the grandmother comes in and Steve Martin's very stressed out because they're going to have another kid. She tells a story of how she was a kid, she used to go to the amusement park. And she couldn't believe a ride like the roller coaster that was so exciting, and so thrilling, and so terrifying all at the same time. Some people just went on the merry-go-round that just went around. But she loved the roller coaster.

And I've always believed if you are going to work with customers and you're going to take on all of the uncertainty that comes with that, you have to be somebody that loved riding a roller coaster. Because it is going to be ups and downs and twists and turns. And if that's not something that your mindset is, I want to get on this roller coaster and I'm going to run back when the ride's over, I'm running back to the front because I want to go again. There's a lot of really meaningful merry-go-round rides that you should probably be on. And so, I think about that as do we have people that are roller coaster riders that are in these customer-facing roles? And do we have some people that we can help move into a bit more of the merry-go-round environment?

Andrew Marks: We've never heard of meaningful merry-go-round rides.

David Karp: I'm trying to honor the merry-go-round riders just because I'm not one. There's joy, I'm sure in the merry-go-round. There has to be.

Andrew Marks: Would that be like the small world? It's a small world would be a meaningful merry-go-round? Because it's this kind-

David Karp: You're going to put this song in my brain now and I'm going to be so mad at you later. I can't even tell you.

Andrew Marks: It's a small world, yeah, okay, there you go.

David Karp: Exactly. I'm ruined. My day is over. Thank you.

Andrew Marks: Awesome. Yeah, you just text me later, let me know that you're still-

David Karp: You bet. You bet.

Andrew Marks: ... tossing that around your head. What about you Lorenzo?

Lorenzo Serva: I like the analogy of the merry-go-round. I think it comes down to ability to make and justify your decisions with limited information. So you're going on the big ride or you're going to merry-go-round. Well, what do you want to know before you take the mistake situation? You want to know that there's some sort of safety net. Now you don't need to understand exactly how it works, but you want to make sure it's not going to be killing you. And how that relates to change management in a offer context, I suppose. It comes down to the fact that you want to know that the organization by and large knows the direction you're going to and then you need to trust the system. And trust in the system, meaning you will need to make some decisions and they're going to be based on limited input.

You're going to be held accountable for certain outcomes and everything else is for you to figure out. You have some tools that help you navigate, you might have playbooks, you might have stories, you can have [inaudible] commerce. But there's an expectation that you need to choose your own adventure. You must be empowered and comfortable with that. I don't think change is intrinsically hard. What makes it harder is not knowing people are expecting from you, there's not [inaudible] of outcomes. And that's what makes it stressful.

Andrew Marks: I think it's both that, but I also think it's a combination of resilience and psychological safety. 60% of employees with low resilience and low psychological safety feel burned out, but only 5% of highly resilient employees with psychological safety report burnout. So it's as much of the transparency that you speak about and that we talked about during the prep call as it is about just having the right mindset. So Toby as once again, as a change management expert, how much of successful change management comes down to the mindset of the people that are going through the change?

Toby Lucich: Boy, great question. I'll stay with this roller coaster analogy because I think it's a good one. If I'm getting on a roller coaster with David, neither of us have been on it before. We're both blindfolded. If I don't feel that gate latched down over my legs, I'm really nervous. Not only can I not see where we're going, but I don't have any assurance that I'm going to make it off the ride. And at the end of the day, that's something I'm interested in. Did I fulfill the objective I set out for? Chances of success high or am I going to splatter? But if David's been on it several times as a leader, he's telling me what's coming next. He assures me that there is a measure of safety. I'm not going to fall out the first time we flip upside down, my blood pressure comes down a little bit.

And so the only way for me to get into that mindset is when we start to have these conversations about being vulnerable as leaders, we don't always know where the next turn is going to be on the roller coaster. And I think in business, this roller coaster, we don't know how many times it's going to flip or if it's going to stop upside down as it often does. And then we have to regroup and figure out how we go from there. So I think some of the mindset is challenging people to take more ownership and accountability over their own reactions to change as they come up. But also thinking about what is it that we can do to help them feel safer, psychological safety. How do we help them feel safer that they can misstep or occasionally fumble without everything having a life or death consequence.

Andrew Marks: And folks, just a reminder, we will be taking questions here in about 15, 20 minutes. So please use the Q&A functionality to ask your questions. And if you see one on there that you would like to see answered as well, use that upvote button. So okay, that's a great kind of segue then to my next question. So when you communicate about change, how much are you actually infantilizing your team? That's actually a word. When you carefully craft messages to ease concerns or manage emotions, are you treating them like professionals who can handle reality or like children who need to be protected from it? And what would happen if you just told them the truth, including the fact that you don't have all the answers? That actually was my MO with my team, much to the chagrin of my boss and our HR department and sometimes my CFO. I was overly transparent.

But I felt from my experience, that built up a lot of resilience in my team. They knew that I wasn't just sugarcoating things, I was being honest and upfront. And that seemed to work for me in all of my leadership roles. You still can't necessarily tell them everything, but you can tell them a lot. You can tell them a lot more than what my leadership was telling me to tell them.

Lorenzo Serva: I had a very good manager in previous job and what she did, she was really good at telling what she did know. And also she was very good at calling out when she thought we were filling that gap with negativity and unpacking assumptions. And that made him the team vert self-aware that we were working in environment with a little bit of information. It's something I took on myself in my leadership practice. How can I build a picture and acknowledge the gaps without having people to feel like, oh, I need to put something in there. I cannot live without the bit of information. How can I build a culture where it's okay to acknowledge that we don't know and maybe we'll never know. And despite that, just to keep going, do what you need to do and there's feedback systems in place.

Andrew Marks: Part of that transparency, I think, Lorenzo is when you don't know, you say, "Hey, we don't know." [inaudible] yet only 19% of associates trust their CEO to tell the truth versus 52% of executives who do. So there's a huge disconnect. The transparency that we think we're providing isn't landing.

David Karp: And I think being aware of different ways of communicating and what a CEO may say versus what one of us may say, how we can be intentional about creating connection points. I think even if we are transparent as leaders, but people around us are not, people will see those disconnects and it'll discredit all of that really transparent communication. So I think part of it is when you're going through a significant change, my ability to be transparent includes my ability to be aware of what people are hearing from others and helping close those gaps. I've had situations, I've been told that I'm transparent, but I'm way too positive. I always see even if I don't know an answer, we are going to be fine.

And so, I've had to surround myself with people who can help me say, "Hey, sometimes you are going to lose credibility even though you're being transparent." Because you have to be aware that not everybody's going to see the positive. And so how do I also make sure that I'm giving a balanced message that's transparent, that it's going to connect with other messages people may hear. So I think because of that, it's also created some complexity and extra responsibility for how we communicate.

Toby Lucich: David, I'd add onto that and say that when we speak as the leader in that official capacity, I think in our personal lives we see so much messaging that is so curated and so massaged and so overly produced that sometimes it's hard to know if it's an authentic message or if it's the party line. And this is true of things we both support and things we don't. And so one of the strategies that I've seen teams successfully employ is not just me as a leader saying it from the front of the room, but also saying it in the cafeteria. And also saying it in the Sales office and saying it to the janitorial staff. There's an alignment piece that has to take place. And in today's hybrid landscape, it's really tough because I may not touch everybody in the office or I may be working with Lorenzo half a world away and I can't necessarily have that easy water cooler conversation. So this idea of how we connect and whether or not the message is perceived as authentic, I think, is also this tricky part that we're dealing with in today's environment.

Andrew Marks: Well that authenticity breaks down when they're hearing different things from different people. And if your employees or your groups of employees are hearing different things, that's the problem. I've been in plenty of situations where I've been very transparent and then one of my team members is talking to somebody on the Sales team or in Engineering and they've heard something different.

David Karp: And I think it's, again, compounded by the fact that we're not all in one place. We have lots of different channels of communication and a lot of times you walk out of a leadership room agreeing on a message, this is what we just decided, this is what we have to go communicate. And then by the time you get a couple steps down the road from each leader, because we communicate differently, even if our intention was good, the message whether we all want to be transparent, it still gets disconnected. And so, it goes back to it's not just a one-time delivery of message. I think part of what you were saying Toby, was it's consistency, it's repeating that message, it's finding places where there's differences. And being committed to doing the work to say, I want to help resolve that difference. And that's really where I think the hard work comes, especially because we're so distributed now. And people hear things, Slack, Zoom, in the room, wherever they're hearing it, it's in so many different places.

Toby Lucich: A default communication rubric or rule of thumb is five to seven times, five to seven ways. I don't know anybody that has the time to do that in today's work world. And it's exhausting. And by the time you get to that seventh repeat of the same message, it's also gotten boring. We've got 100 other things pounding for our attention. And so I totally agree, David, maybe the trick is really think about how we activate others, that sharing of power again. And trusting that the most simplified message is likely to hold the most fidelity over time too. There's a lot of nuance that doesn't serve us.

Lorenzo Serva: Yeah, absolutely. It's very important if you've got a complex message, I think it's very important to chunk it up and deliver the top line and make sure that it's understood and then make people aware where to go for further details. Do not overwhelm people notch. That feels defensive, that feels messy, that feels you're trying to cover up with an over delivery of information for the lack of direction. You're just trying to bombard people and that's one problem. The other problem is that you are confusing on different layers or different channels have different message. And so people feel that there's a survival mode that they need to activate when they need to piece together a story by going to an investigative mindset. They need to start looking for gotchas or they're telling me this, so might be something more. Where do I go finding what's real happening? And that's really negative. You really need to neutralize that.

And if I flip the script on the customer side and going through a change management where a customer comes into it and applies in turn to the importance of building champions. So having someone other than yourself as a reference, different level of the organization, different level of maturity markets that can be your loudspeaker for the change message when you're not in room. So you own the top line, everything else there's a system that helps you amplify. There's important reason it's better, it frees up your time to evaluate the strategic direction or whatever piece of activity you're completing. And actually empowers people. Boils down to peace understanding and peace sensemaking of the change. I think it's very powerful. We should not... There's the ultimate test for the team that they can live through the changes that they show your in practice, how they go about sensemaking as the change comes about.

Andrew Marks: And I like that, that consistency though is super important, that consistency across. Even if you have middle management that's helping you with that message, you need to make sure that everybody is saying the same thing. So most change management advice focuses on creating stability and predictability during transitions. Yet a little interesting nugget that I found. Organizations focusing on stability during a change still see 60% to 70% failure rates even with careful management, only 34% of initiatives succeed. So what if that's backwards? What if the goal should be building teams that don't need stability, teams that can perform well in continuous uncertainty? What would you do differently if that were the objective?

Toby Lucich: Go ahead, David.

David Karp: Go ahead, Toby. I've got something, go for it. I thought you were going.

Andrew Marks: Come on, come on.

David Karp: Toby and I are looking at each other. Go for it. Go for it.

Andrew Marks: I'm looking at all you guys, what's going on?

Toby Lucich: Yeah. I'm chuckling to myself because I'm trying to think of the last time that I had a stable and predictable job. And it'd have to probably go back to those jobs that we had in high school where we had absolutely no authority to do anything important. We were just being hired from the neck down. You show up, you do the same thing every day and things didn't change at that end of the shovel. So-