More calls. More emails. More activity.

Then AI arrived, and many teams tried to automate the same model.

But what if the problem wasn’t needing a faster version of the old playbook?

What if the real opportunity is to use AI to make people better at the things only humans can do?

That’s the question behind my conversation with Craig Rosenberg.

Craig has been gathering some of the best SDR and pipeline leaders in B2B through Scale Venture Partners’ Pipeline Council. What he’s seeing feels less like a completely new playbook and more like a return to fundamentals, with much better tools.

AI can help us choose the right accounts, recognize signals, research buyers, practice conversations, and move faster.

But the last mile still comes down to relevance, judgment, taste, trust, and human connection.

About this episode

Craig and I have known each other since the early days of B2B marketing and demand generation. I followed his Funnelholic blog back in 2008, and he reminded me during our conversation that my book, Lead Generation for the Complex Sale, was one of the first B2B GTM books he read.

Several things Craig had recently been sharing from Scale’s Pipeline Council brought us back together.

One of the big questions they’re working through is simple:

What does a high-performing SDR motion look like now that AI can do so much of the work SDRs used to do?

The answer isn’t fewer humans everywhere.

In fact, Craig is seeing AI companies hiring SDRs and experienced enterprise sellers as they move beyond product-led growth and into harder-to-reach markets.

Craig and I discuss:

• Why automating the old activity-based SDR model didn’t solve the pipeline problem
• How Glean uses AI to help SDRs get better at human conversations
• Why Craig believes the “last mile” of selling is still human
• What unmistakably human outreach looks like when buyers are surrounded by AI-generated messages
• Why AI companies are hiring SDRs and experienced enterprise sellers again
• How ICP and signals help teams focus on the accounts most likely to buy
• Why selling AI is becoming harder and business process may become the new software moat

About Craig Rosenberg

Craig Rosenberg is Chief Platform Officer at Scale Venture Partners, where he helps build and lead Scale’s go-to-market platform for software companies.

Before joining Scale, Craig was Distinguished Vice President in Gartner’s sales practice. He joined Gartner through its acquisition of TOPO, the research and advisory firm he co-founded.

Long before that, many B2B marketers and sales leaders knew Craig as the Funnelholic, where he built a following writing and speaking about demand generation, sales development, and B2B go-to-market strategy.

He also co-hosts The Transaction podcast with Matt Amundson.

Connect with Craig

Craig Rosenberg on LinkedIn
Scale Venture Partners
The Transaction podcast

Chapters

00:00 What Top SDR Leaders Are Figuring Out
04:41 How Glean Uses AI to Make SDRs Better on the Phone
09:09 The Last Mile Is Human
12:46 Why AI Companies Are Hiring SDRs Again
15:33 What Does “Unmistakably Human” Look Like?
22:06 Why Enterprise Prospecting Shouldn’t Always Scale
23:36 ICP, Signals and Choosing the Right Accounts
25:25 Why Selling AI Is Getting Harder

A few things worth taking away

• The old SDR model treated people like “human robots.” Automating the same activity-heavy motion with AI didn’t solve the underlying problem of relevance.
• The better teams are using AI to prepare humans, not replace them. At Glean, AI supports account selection, research, signals, and practice while SDRs focus on getting better at live conversations.
• The last mile is still human. AI can provide information and suggestions, but judgment, taste, relevance, trust, and relationship building still require people.
• Being unmistakably human sometimes means admitting what you don’t know. AI can help you understand a buyer’s situation, but it shouldn’t create expertise or experience you don’t actually have.
• AI companies are hiring SDRs and experienced sellers as they move beyond product-led growth into enterprise markets. As Craig put it, “The minute you want to talk to people that aren’t coming to you, you need people.”
• ICP matters more when data is abundant. Craig shared an example where ICP opportunities converted at 37% compared with 17% outside the ICP. Signals then help determine when to reach out and what may matter.
• AI is also changing software competition. As products become easier to build and replace, Craig believes companies need to expand from TAM to “Total Available Problem” and become deeply embedded in customer workflows and business processes.

A few lines that stuck with me

“The reality is the most important thing now is trust building, humanity and relationship building.”

“It’s that last mile, which is the human.”

“The minute you want to talk to people that aren’t coming to you, you need people.”

“Getting into AT&T doesn’t scale.”

“There are accounts that are the absolute best fit for you right now. Why would we spend time on anything else?”

“We’ve moved from TAM to TAP, which is Total Available Problem.”

Listen and subscribe

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Transcript

Brian Carroll: Welcome to The B2B Roundtable. I’m Brian Carroll, and I’m excited to have our guest today, Craig Rosenberg.

Craig is the Chief Platform Officer at Scale Venture Partners. What Craig’s doing is helping them build their go-to-market platform so that they can bring this expertise to help software companies drive growth.

I’ve known Craig quite a while. We go way back in terms of what we were doing in the early days of B2B marketing and complex sales. I started following Craig’s blog, The Funnelholic, going all the way back to 2008.

Craig first shared a Pipeline Council they’re doing with some of the top SDR leaders in enterprise and software sales. And then Craig did a post with Jason Vargas talking about the “taste layer” and bringing that to the SDR rep.

What I’m excited about, Craig, for us to talk about is, you know, the more things change, the more they are the same.

What’s coming up in the Pipeline Council that the rest of us aren’t talking about yet?

Craig Rosenberg: Well, first I thought it would be important for the audience to know that, yes, you found me through The Funnelholic, but everyone found you through your book. Was it Lead Generation for the Complex Sale, I think was the name?

Brian Carroll: Yeah, yeah, it was.

Craig Rosenberg: And that was like the book.

I mean, Brian, you were the OG out there with the book and talking about it. So I think that’s amazing to bring up.

And even the fact that you brought me here because you saw these posts, for everyone who’s wondering if it’s important for you to share what you’re working on and thinking about on social, I mean, look, that’s how I met Brian in the first place.

He had a book and was doing the speaking circuit. I had a blog. And then recently, he brought me back here after he read one of my posts on social.

So there is a lesson in your intro in and of itself.

Brian Carroll: That is true. And you also do a podcast, which is awesome.

Craig Rosenberg: Thank you.

Brian Carroll: So let’s go back to what’s coming up in the Pipeline Council that the rest of us aren’t talking about.

Craig Rosenberg: I have two councils. I’ve got one where I brought together the folks that have figured it out. I’ll talk about that in a second. Then I’ve got my regular councils, which bring together people who are still trying to sort this out.

Brian, from our conversation before, I’ll just go on the negative side. There was a moment where SDRs were basically human robots, right? They were basically conveyor belts of information.

It was about how many emails could you get out, in some cases how many calls, and then the messaging was sort of one message. It was all about output. Or I think you said they were activity-based, right? They were machines.

So we had that moment.

We had to come out of that and sort of accept that the original iteration of AI here, and the way people thought AI would work, would be to somehow automate that motion, which was a highly generic, activity-based motion.

We had this run of SDRs being these human robots and delivering activity. And frankly, let’s face it, they got meetings.

Then everything changed and it got really hard. Then we said, “Well, we’re going to solve it by using AI to deliver what they were doing as robots,” and that didn’t work.

Everything got really confusing. That’s why I put the Pipeline Council together at the Rosewood, so I could start learning more.

I work with a woman named Christina McMillan, who I’ve worked with for years. She was at TOPO with me, but she was an SDR consultant for years.

I said, “You know what? We don’t know anymore. We’ve got to go figure this out.”

So we bring together the Pipeline Council, and it’s really interesting because we actually do know.

The reality is the most important thing now is trust building, right? Humanity and relationship building.

What we missed for, call it eight or ten years, was that, because we didn’t need it.

Now, the truth is, from watching you, reading you, and listening to you for a long time, you would say, “Wait a minute. That’s what I was talking about back then.”

But the truth is, I think we kind of lost sight of that.

There were some really interesting things I learned from the Pipeline Council.

I’ll give you an example. This guy Joey Lopez, he’s at Glean, and this guy amazed me. So I’m just going to give you this example of what he does.

Most everything is AI and automated. Who they’re going to talk to, what types of companies, those things are served to them.

Because, by the way, Brian, one of the things that was also happening during the SDR-as-robots phase was they were choosing their own accounts. They were going into ZoomInfo and just downloading names and sending emails.

There was no thought process on who we should talk to.

The AI will research the company, help them identify both educational information and signals. The AI actually sends emails for them.

What he believes is: Can I focus on one thing?

His choice is to focus on the phone, which is a highly converting channel for them. So they train and they practice this all the time.

But ready for this?

He’s a football, wrestling guy. Every day the SDRs come in and they huddle like a sports team.

He’s like, “Look, you don’t just practice before the game. You get in the locker room and you go through the game plan.”

But they actually practice.

Let’s say that day they’re going to call CIOs. They all get trained on the CIO persona: what they care about, what their challenges are, day in the life.

They get trained on the type of messaging that works under different scenarios.

Then they go practice. Then they come back and huddle. Then they all spend the whole day calling CIOs, and that’s it.

Then they optimize against it.

It is just brilliant, right?

Brian Carroll: It is brilliant.

Craig Rosenberg: I’ve never heard anything like it.

I told him, “Look, that is better than what me and Brian used to do.”

In the practice, they’re using sales simulations where they can practice against the CIO persona, which is AI.

Everyone asks me, and I’m like, look, I’m in a venture firm. We love AI. But it’s that last mile, which is the human, which is the thing that we’re learning.

Brian Carroll: That’s right.

Craig Rosenberg: He trains them on the human, and they go in and have these conversations.

Then they listen to calls together, maybe like a halftime, and they optimize. That day, they just do really well with that type of person.

I thought that blew my mind. It was incredible.

The other things I saw were highly personalized direct mail. There are these groups where they’ll actually create custom gifts for someone based on what they care about.

An example would be, if developers have a high predisposition for Legos, there are groups that do personalized Legos. Or they might know someone is way into archery, so they’d send them something around archery.

It was these highly personalized gifts.

And the conversion rates are the most important thing. We have to live by the numbers, even if it’s a great idea.

Sometimes I have a great idea every week that doesn’t work.

Brian Carroll: Sure. I mean, that’s part of life.

Craig Rosenberg: Now that we’re our age, we can relate to this.

But the conversion rates are really high. Everyone says, “Well, that’s a gimmick.”

No, it’s not a gimmick. It’s personalized.

If you send me a stress ball, that’s not going to work.

Brian Carroll: Mm-hmm.

Craig Rosenberg: But if you show me that you know me, then that’s going to be infinitely more effective.

The other thing that was surprising to me was there was a guy in cybersecurity, which is one of the hardest markets to email, and he improved email reply rates to 6%.

We haven’t seen 6% since 2021.

What he did, again, was make the emails more relevant, more personalized.

He tore everything down and rebuilt it in a way that was more highly relevant and highly personalized.

So if I had to leave a theme, there are some really fun channels and tactics that I learned about, but at the end of the day, I think the key is that last mile.

And I think that’s what leads you probably into the taste layer.

Everyone wants to know what humans are going to do.

Well, the humans are there to make sure that we’re building a relationship, that we’re being relevant, that this is something tasteful that we would send to someone.

That’s what we saw. We went around the table, and that’s where we learned all those things.

That Joey Lopez example, what do you think of that? That was incredible.

Brian Carroll: I love that.

Going back, Joey took it to another level. When I was running BDR teams, I created something I called “How to Talk to Me,” which was doing what Joey was doing.

But with the role-play, we didn’t have AI to do role-play. It was our best educated guess on a persona.

We did focus on just calling that persona because people would be reaching into multiple people within an organization.

I just think getting that level of specialization matters.

In sports, you need to get reps in, but they were practicing the reps before they talked to a live person. Then they were able to go deep, which I think is brilliant, because that’s how people get good: having that focus, having the understanding.

It also helps younger, less experienced people who haven’t had the life experience, maybe calling an executive, to actually know how to talk to them.

Craig Rosenberg: Yeah, for sure.

By the way, one thing on the experience-versus-not thing. It’s a challenge because we do typically use less experienced SDRs in this process.

But, on the other hand, it was interesting. We had a really successful leader. He’s not allowed me to talk about who he is ever. It’s a long story.

He’s got a highly successful SDR team that’s scaling, let’s say, a hundred. Remember when everyone told us they were dead?

Brian Carroll: Yeah.

Craig Rosenberg: His issue with the experienced folks is that they couldn’t approach the buyer the way he wanted to, which was in a much more personalized way.

If you think about it, if someone was highly successful during the SDR robot phase, are they really more experienced?

I don’t know.

Brian Carroll: Really, they aren’t.

They’re experienced being repetitive and doing activity. But when it comes to actually connecting with people and being relevant, that’s something you need to train.

It’s a skill. It’s something people need to develop, and it doesn’t just happen.

Craig Rosenberg: Yeah, for sure.

I was going through the numbers everyone was giving me. I’m like, “Who’s hiring?” Everyone raised their hand.

It’s nuts because everyone told me SDRs were dead.

Brian, I think we’ve seen this before, though. There was a moment where everyone tried to kill the SDRs.

They keep trying to kill the enterprise sales reps, saying, “No, those old guys, they don’t know anything.” And now they’re getting hired at prices where, I mean, they’re unaffordable.

But it’s the same thing. It’s your same theme.

You need AI to help everything go faster for the human, but at the end of the day, that relationship is built with these people.

We’re seeing that across the board.

These AI companies came up through PLG. Some get to a billion without hiring go-to-market.

But guess what?

The minute you want to talk to people that aren’t coming to you, you need people.

Brian Carroll: That’s right.

You had shared something, I think this came from Adam Schoenfeld, about 39%, and maybe it’s higher, of AI companies hiring SDRs.

Everyone thought these companies were building the technology that’s supposed to replace SDRs, supposed to replace salespeople, but they’re still hiring.

So what do you make of this?

Craig Rosenberg: First of all, you are right. It’s probably higher because that was six months ago when Adam did that.

He looked at 150, I think a little more, top AI companies. Thirty-nine percent were hiring SDRs and SDR leaders.

A year ago, I was talking to experienced SDR leaders who were crying because they weren’t going to hit their mortgage. Now they’re getting paid more than they ever did.

Those top AI companies, frankly, look, I’m in venture, but you see their numbers. It’s extraordinary.

They’re doing it by people catching fire from a brand perspective very early on, people coming to them, and typically a PLG motion.

I’m all in favor of that.

What we’re seeing now is that whole cohort is trying to get into enterprises, new markets, even mid-market that didn’t necessarily come to them.

At a certain point, you have to do this.

And they’re not just hiring SDRs. They’re hiring, like I said, experienced sales reps that were supposedly dinosaurs and out of the business.

The second thing, though, is what we just talked about.

I actually do believe there was a moment where SDR leaders were running the same playbook and they failed. Then they went to the next place and they failed.

So in defense of the sort of fall of the SDR, the SDR leaders had not adjusted.

Now they’ve adjusted, and now you’re seeing folks starting to share successful implementations.

It was a return to humanity in many cases.

But I will say AI is predominant in their systems and how they cue everything up. There’s the ability to provide information SDRs have never had before, the ability to give them both educational information and signals that tell them when to reach out to someone and how to be relevant.

Those things are real.

The fact is, what we need is that last mile to be people.

That has been the breakthrough.

Brian Carroll: You’ve said this a couple of times, bringing humanity back.

What would you say “unmistakably human” looks like now, today?

Craig Rosenberg: Man, that’s a really good question.

Brian Carroll: I read probably a dozen things on LinkedIn where someone’s saying, “How not to sound like you wrote by AI.”

And I’m like, why not try writing?

Why not try actually writing yourself in your voice?

Because there’s a backlash happening too, you know.

Craig Rosenberg: Yeah. I know. You’re right.

I think there have been two moments that turned people off to generic messaging.

There were SDRs as robots just flaming the market with emails. Then there was, like we said, “Well, we could solve this with AI.”

Even today, I got emails this morning that were clearly not written by a human.

We’re surrounded by AI messaging all over the place. And so when we get a human, that’s something that’s really relatable.

I’ll give you an example. You said try writing.

I use AI every day. I originally tried to have AI write emails to folks, and then I said, “Okay, well, that doesn’t work.”

Then someone said, “Well, it’s easier to be an editor.” And I used to say that.

Then I tried editing it, and it was too hard.

So I went the other way.

I use AI, let’s say I’m prospecting, to tell me what kinds of things work. It can help me with the structure or the rubric of an email.

What types of things work in the first sentence? Stuff we train on.

It can look and say, “Hey, the best reps are doing this at the top.”

That helps me a lot.

I ask it for ideas in bullets. That’s my new thing.

I get these great ideas, but then I write it.

So I’m still faster, but more importantly, I’m better. AI does help me a lot, but I just couldn’t have it write it anymore.

If it’s AI-patterned or templated, it just won’t work.

I’ll give you an example of humanity.

I was just talking to John Barrows, and he said, well, a young SDR gets this signal about a merger. He’s never seen a merger before, and he goes and writes about it.

I’m like, “Dude, you can’t do that. I’m not going to answer.”

So it’s like, you want to use AI?

Well, tell me what happens in a merger. Tell me what things might be happening at this organization.

Now I’m going to take it and write something more heartfelt.

I might have even written, “You know what? I don’t know a ton about what happens in mergers. But I do know, just having experienced this, that this, that, and the other might be happening in your business. And that’s why I feel like we might have the ability to have a conversation about this use case.”

Just being humble and approaching it that way might have worked.

The other way is to do your own research and be okay with not being perfect.

I thought that was a really good example from him because that would be an example where we’d use tech.

We’d say, “It’ll identify if there’s a merger, then it’ll put together a message.”

It’s like, yeah, but that person got 200 messages that all look the same.

That shows zero understanding of that person and what they might be going through.

So what’s your differentiator? How are you going to do it?

I think when we talk about humanity, we have to be able to tell the buyer, “Look, it’s worth talking to me.”

And that actually has to be done by you, the person.

It’s one of the reasons I’m surprised people answer their phones, because I certainly don’t. But we’re seeing the data, and it does work.

It works when you connect because ultimately that’s two humans connecting, having a conversation, and being able to talk it through, which says, “No, I’m not talking to a robot.”

Brian Carroll: Yeah, and I think there is a lot to what you’re saying.

My first job as an SDR, I was calling to set up appointments for sales training. My first day, I knew nothing about sales.

I was frustrated in the week, and Julie, the manager, said, “Brian, just be people with people. Why not own the fact? You’re 22 years old. You don’t know anything about sales. And the irony is you’re setting up appointments for sales training.”

The point being, the admission of who you are and what you don’t know can open up possibilities.

I could talk about, “I’ve learned so much in the sales training already.”

I think there’s this point that we still need to go back and learn what is unmistakably human and do more of that.

I wanted to go back to when you did the meeting at the Rosewood. Was there anything that surprised you the most or was counterintuitive that you came away with?

Craig Rosenberg: Counterintuitive?

Well, I actually would say the most surprising thing was that I wasn’t surprised.

I mean, that’s cheating, but I think everything ended in the same theme that we just discussed.

I’m surprised people still answer their phones. They do. There’s tech to go do that.

By the time we got to, let’s say there were 12 people in the room, when we got to number four, I was like, “I got it.” Then they kept going, and I’m like, “I still got it.”

I’ll give you another one that was big.

The SDR thing kind of blew up a year and a half ago. Now it’s back, and it’s like, what were the things that we forgot?

Well, one, they want to get promoted.

One of the people in the room was like, “One of my keys is that I have about 70% of my SDRs get promoted into sales.”

I’m like, “Okay, that’s amazing.”

And she’s like, “Now more talented people come. They stay longer because they know they’re going to move up.”

I was like, my gosh, that’s an old theme that’s come back.

Maybe the thing to say is that what’s old is new again.

A lot of the fundamental things that we used to discuss with SDR team building, that I kind of forgot about, came back.

Brian Carroll: AI has allowed us to scale activity. It hasn’t allowed us to scale relevancy unless you use it properly.

Craig Rosenberg: Yeah.

I actually do have a fun one for you.

Brian Carroll: Okay.

Craig Rosenberg: A fun one and one that we already knew, but is really important.

The fun one did not come from the Pipeline Council. I like to just talk to people.

These hot companies that are sort of breaking down doors, I just want to talk to whoever’s doing it.

There’s a company in New York called Attention, and one of their highest-converting channels is the SDR taking a gift and walking in the doors of their target account.

Brian Carroll: Wild.

Craig Rosenberg: So I called him. He’s like, “Yeah, it’s the field SDR.”

They also get a LinkedIn message saying, “Hey, the Attention guys just brought that.”

It’s that motion because, guess what? We give donuts. It has our name on it. Or we could give whatever.

But the fact that we made that personal effort, having the person who’s trying to reach out to someone show up at the admin’s desk and hand them that, that’s the ultimate in conversion.

Now, you can’t scale that.

But look, you and I, you’re the complex sale guy. I’m the enterprise guy.

I keep telling people, guess what?

Getting into AT&T doesn’t scale.

You have to find your way in, then find your way across, and continue to do that.

That was a surprising channel for me and really interesting.

The other thing, though, that I did not mention before, that people are doing a lot better across the board, is ideal customer profile work.

I knew this at TOPO, and people didn’t believe me because everything was about meetings. They didn’t care what.

I kept saying, “Forget the term account-based marketing. Don’t worry about it. The most important thing is there are accounts that are the absolute best fit for you right now. Why would we spend time on anything else?”

It was funny. When I’d go in and they’d say, “Can I look at the forecast?” I’d say, “Well, let’s run it against the ICP.”

It was obvious.

You’re getting a 37% conversion rate against the ICP and 17% against other accounts.

That should tell you everything.

What we see now, with data and the ability to do this, is that a lot of these successful teams are doing a way better job of choosing the accounts.

The second part is, with signals and these things, you’re able to figure out when to reach out to them and what to say.

Those two breakthroughs are huge.

Brian Carroll: Yeah, and I think back, you brought up my book.

By the way, it’s coming up on 20 years since that book came out.

Craig Rosenberg: No way. I’m getting old, man.

Brian Carroll: Yeah, I can’t believe it either.

So 20 years ago, in 2006, there wasn’t an abundance of data.

We now have an overabundance of data. It’s: What do we do with it?

We can move from thinking ICP is how you build a list to, no, your ICP is how you know who’s relevant, and you focus on just those.

You aren’t trying to build the biggest list possible. You’re trying to build the most relevant list.

It makes perfect sense.

Craig Rosenberg: Yeah, I know.

Brian Carroll: What are you seeing right now, as you look across your portfolio, that a lot of us might miss?

Craig Rosenberg: Well, I’d say to everyone, you’ve got to stop firing your CMO just because things are tough out there.

The movement there has been extraordinary in terms of people getting shipped out.

There is a point there, which is messaging matters.

I think it’s really hard right now.

It’s been a killer. CMOs who are pretty good are fighting with the organization, trying to find the best message and not getting there.

Look, I work with startups, and it’s hard to run marketing at startups. It’s really hard.

The good news is everyone wants to talk about AI.

The bad news is everyone’s selling AI.

AI is not the same as SaaS.

Everyone says, “Well, yeah it is.”

No, because SaaS you could load it and go. AI has to integrate with your data. That’s why you see this sort of forward-deployed engineer thing.

To really understand it, you have to be able to get it in and get your data moving through the system.

So it’s different.

If you think about it, everyone’s pitching AI.

Everyone knows they need to go to AI, but now everyone’s afraid of it. There’s also a whole naysayer element in the buying committee that makes it even harder.

But more importantly, there are so many more products out there.

You’re selling into your category, where there may be 35 other companies.

Then you have horizontal AI companies like OpenAI and Anthropic coming at you from the other side. You’ve got other AI companies coming in and tangentially touching your message and your value proposition.

That makes the ability to distinguish yourself really hard.

Here’s the big thing.

For AI companies, many of them come into the market as a wedge. They found a hole in the market and they filled that hole.

In the SaaS era, if you found that wedge, you would be able to run with that wedge, go raise lots of money, and dominate by focusing on that wedge.

Now you can’t, because it’s too easy to make software and it’s too inexpensive.

We like to joke that four kids in Brooklyn will create your product in a month and be coming at you.

If you sit on that wedge now, you’re actually asking to get flanked.

That’s an incredible challenge.

A company today has to go in via its wedge, and then the things that used to happen eight years after a company existed, you have to do now.

We have an investor here who said we’ve moved from TAM, looking at the biggest market, to TAP, which is Total Available Problem.

We have to expand the problem set as fast as we can.

Brian Carroll: Wow.

Craig Rosenberg: The other thing is moating.

Moats are really hard because, like I said, it’s the same problem. Building software is easier than before.

Then you’ve got the threat of the frontier labs. Anthropic can take you out in a night and not even know you existed.

Your moat now is integrating yourself into business processes and workflows as fast as you can, because that makes you harder to pull out.

It’s funny because everyone’s talking about CRM and whether there are new CRMs.

Except the reason SAP and Salesforce don’t die is because they become the business process.

Tearing them out means you’re tearing down your entire business process.

Everyone thinks it’s the data.

Data moves now. You can move data in less than a day.

It’s actually the business process.

There’s a lot to learn there for these companies.

The faster you can become integrated into their business process and become the business process, the stickier you are and the bigger your moat can be.

But if you don’t do that, then you’re easily replaceable.

I talked to a RevOps leader I’ve respected and known for years.

He said, “We look at our tech stack every month, and we’ll tear stuff out every three months.”

I’m going, “Is that good?”

He’s like, “Yeah, because guess what? I can always look at what’s better.”

Ripping and replacing is actually not that hard unless they’re dug into my business.

Those are things I think people may not know about that are really important to take in and think about.

How you sell, how you message, what you do in the sales process, and what you do in the post-sales process are different.

There are big challenges today. There are different approaches to how you think about things.

If I had to give you anything that I’ve learned, that’s more of what I’ve learned from the investors looking at the market that I’ve found fascinating.

Brian Carroll: Well, Craig, I just want to say thanks for the conversation today.

It’s been so great catching up with you and hearing your perspective.

The more I listen to you, the more I’m remembering how aligned we are in so many ways.

So I just want to say thanks for joining us and being on the show today.

Craig Rosenberg: Yeah, thanks for having me.

It’s great to see you and talk to you again.

I’m going to have to flip through your book again. That was one of the first B2B go-to-market books I ever read.

So it’s really cool to catch up.

But the go-to-market system underneath the business may still be built for an earlier stage of growth.

Corey Livingston shares why rebuilding your GTM should start with understanding and clarity, how marketing can build trust with sales before results appear, and what leaders should measure before the pipeline is visible.

About this episode

Financial reports show how a business is doing, but they don’t show if the go-to-market engine is ready to support the company’s next phase of growth.

That is the tension at the center of this conversation with Corey Livingston, Vice President of Marketing at DartPoints.

Corey has spent more than two decades leading B2B marketing through growth and change. She has worked inside companies moving upmarket, entering new segments, and trying to build several GTM motions at once.

Her starting point is not another campaign.

It is understanding the growth hypothesis, determining whether each motion is in the build, activate, or scale phase, and getting the organization aligned around what it can realistically produce next.

We talk about why moving into enterprise requires more than changing the target account list, how marketing earns credibility with sales, why alignment must extend below the CRO, and what leaders often get wrong during the first 90 days of a GTM rebuild.

About Corey Livingston

Corey Livingston is the Vice President of Marketing at DartPoints.

She has more than two decades of B2B marketing experience, including leadership roles at Level 3 Communications and OneNeck Solutions, as well as fractional CMO work across multiple companies.

Her work focuses on GTM strategy, sales and marketing alignment, enterprise growth, and helping companies build the operating systems required for their next stage of growth.

Connect with Corey

Follow Corey Livingston on LinkedIn

Chapters

00:00 Why healthy dashboards can hide a broken GTM system
00:49 What dashboards miss in a GTM rebuild
02:36 Why moving upmarket changes the entire motion
05:35 How to diagnose the gap between strategy and execution
09:02 How marketing earns sales’ trust before results
17:58 How to decide which GTM motion comes first
21:00 What to measure before pipeline shows up
26:23 What leaders get wrong in the first 90 days

A few things worth taking away

• GTM is a lifecycle, not a switch. Leaders need to know whether a motion is being built, activated, or scaled before deciding what to measure.
• Moving upmarket is not just a strategy shift. Enterprise buyers require more credibility, stronger proof, deeper content, and tighter coordination with sales.
• Sales trust comes from clarity, follow-through, and quick wins, especially while the longer-term GTM system is still being built.
• Alignment with the CRO is not enough. Marketing also needs to earn the trust of frontline sales leaders and the people doing the work every day.
• You cannot scale every motion at once. Investment decisions should connect to the company’s growth hypothesis, resources, timing, and near-term revenue needs.
• Pipeline is a lagging indicator. Operational readiness, engagement from the right accounts, and qualified meetings can show whether the motion is beginning to work.
• For an early enterprise motion, one of the most useful questions is: are we meeting with the right person at the right account, and are they moving to a next step?

A few lines that stuck with me

“I look at GTM as more of a lifecycle, not a switch.”

“A corporate strategy and vision is not a go-to-market strategy.”

“Sales trust comes from creating clarity. It comes from follow-through and quick wins.”

“You can’t scale everything at once.”

“You can’t get to pipeline without engagement.”

“Are we getting a meeting with the right person at the right account?”

“Most leaders try to fix things too fast in the first 90 days.”

Listen and subscribe

Subscribe to The B2B Roundtable wherever you listen to podcasts.

Transcript

Brian Carroll: Welcome to The B2B Roundtable. I’m Brian Carroll, and we’re going to talk about something people don’t often talk about.

A company hits an inflection point. The strategy shifts, the buyer changes, and the dashboard shows green. But the system underneath was built for a different version of the business.

The gap doesn’t show up in a report. It shows up when things start to stall, and nobody can explain why.

My guest today is Corey Livingston. She has spent more than two decades in B2B marketing, leading at companies including Level 3 Communications and OneNeck Solutions. She has also done fractional CMO work across multiple companies.

Today, she is serving as the Vice President of Marketing at DartPoints. I invited Corey because she has been through these inflection points in several different seats.

Corey, welcome.

Corey Livingston: Thank you, Brian. It’s great to be here. Thanks for having me on.

Brian Carroll: We’ll dive right in. When you step into a GTM rebuild, perhaps at a mid-market company, what are the things you usually see first that dashboards don’t show you?

Corey Livingston: When you step into a company that is evolving its strategy, in my experience, in almost all cases, that evolving strategy involves moving more upmarket.

You look at the numbers. You look at the financial reports. You talk to all the right people. It tells you what is happening in the business, how it is performing, and its underlying health indicators.

But it doesn’t tell you whether the go-to-market engine is mature enough to support the next stage of growth, the next inflection point, or the new segment you want to penetrate.

You have to start by diagnosing where you are. Where is the business in the go-to-market lifecycle? Are you in the build phase, the activate phase, or the scale phase?

I look at GTM as more of a lifecycle, not a switch.

You don’t just declare that you’re moving upmarket or moving into a PLG motion, or whatever it might be, and then it happens. You have to understand where you are.

If you don’t know where you are in the lifecycle, you’ll end up measuring the wrong things, investing in the wrong places, and expecting outcomes the operating system isn’t ready to produce yet.

Brian Carroll: That makes a lot of sense. Could you give an example, without naming the company, of where that stood out to you and what you did?

Corey Livingston: As I mentioned, I’ve worked across many different companies that were operating in either SMB or mid-market. That was their customer profile, and many of them wanted to move into enterprise.

The deals are larger. The revenue is stickier. There is more opportunity to differentiate.

I used to have a boss who would say, “Where there’s mystery, there’s margin.” There is also more opportunity to be consultative.

Brian Carroll: Mm-hmm.

Corey Livingston: But going into enterprise or moving upmarket, whether it is the lower end of emerging enterprise or the Fortune 500, is not just a strategy shift. It is a motion shift.

The go-to-market operating system for enterprise is fundamentally different from SMB or mid-market.

I’ve worked in environments where companies were pursuing all three segments: SMB, mid-market, and enterprise.

In SMB, buyers move fast. There are fewer people involved in making the decision. The stakes are lower, and the go-to-market engine can rely on lighter content, simpler messaging, and more transactional motions.

You also tend to get much more inbound from SMB than you would from enterprise.

Enterprise is the opposite. The cost of entry and the burden of proof are much higher, not just in what you need to spend, but also in the credibility you need to get the door open.

Enterprise buyers operate in much more complex environments. In my case, I’ve always worked in the IT and technology sector, where IT environments are highly complex.

The stakes are much higher for the people influencing or making the decision if something goes wrong. There is much more risk involved.

They want credibility and familiarity. It is the old saying, “Nobody ever got fired for hiring IBM.” There is still a version of that in our modern marketing world, especially when you move upmarket.

That means your GTM system has to evolve. What worked for SMB and mid-market is not necessarily going to work. It may provide some foundational elements, but the system still has to change.

You need deeper content. You need much clearer use cases. You need reference customers who have worked in these enterprises before. You need strong stories, proof points, more orchestrated outbound, and much tighter alignment with sales.

You’re going to be working hand in glove with sales. You also need a sequencing model that matches how enterprise organizations actually buy, which is a more complicated buying journey.

Brian Carroll: How do you tell when a strategy has changed, or needs to change, but the GTM system hasn’t caught up yet?

Corey Livingston: In my current role and my previous role, I had a significant part in helping shape the GTM strategy.

The first thing I do is understand the growth hypothesis.

When I walk into a business, the first question I ask is: What is the hypothesis for how we are going to grow? What channels are we using right now? Are those the right channels?

I interview the executives, the C-level team, and everyone on the go-to-market team.

The go-to-market team is not just marketing. It includes product, sales, and, in my industry, solution architecture.

It is about doing the research, conducting interviews, and asking the right questions.

Where do people think the go-to-market system is today? How well is it working? Where is it not working?

I’m looking for areas of agreement and areas of difference. I want to make sure those differences are not so significant that they could undermine the strategy we need to build for the next phase of growth.

I start by asking what we have today and whether that operating system can get us to the next phase of growth.

I can’t necessarily determine that on my own. When you’re building GTM, one of my strengths is bringing everybody together, getting everybody on the same page, and listening deeply.

Those are considered soft skills, and I don’t think they get enough attention. But that is the first place I start.

I don’t walk in and immediately start executing a GTM plan.

In many environments I’ve entered, there isn’t really a GTM strategy. There is a corporate strategy. But a corporate strategy and vision are not a go-to-market strategy.

A corporate strategy does not explain how you are going to activate in the market and begin producing results.

You also can’t scale everything at once.

I have to prioritize the areas where we have leverage and anchor everything to the growth hypothesis.

What are the sales quotas? What are the revenue projections? What motions already exist, and where are they in the lifecycle?

If the growth hypothesis says growth will come from retention and expansion, I would start there, unless there is foundational work required that would delay our ability to activate and reach our sales or revenue numbers in a way that conflicts with the plans presented to the board.

Then I look at the next motion. It could be channel, inbound, or events.

Which motion is most mature? Which one can we activate fastest? Which one aligns with the near-term revenue picture?

That is where I start.

Brian Carroll: Those are some great pointers for people thinking about moving upmarket or entering the enterprise.

You mentioned sales quotas and getting alignment with sales because this is a significant shift for the organization.

Corey Livingston: Yes.

Brian Carroll: How do you build trust with sales before you have results to point to?

Corey Livingston: That is always much more art than science.

In my experience, sales trust comes from creating clarity. It comes from follow-through and quick wins.

It is hard to earn sales trust, but it is very easy to lose.

I don’t necessarily come in with a 90-day plan for sales. I would probably do that for my CEO, but not necessarily for the sales organization.

They need clarity. They need enablement. They need early wins.

My strategy is always to build trust by helping them move faster, not by asking them to wait for the perfect GTM system to materialize before I deliver anything.

Early in my career, and I think this is true for many of us when we’re starting out, we think we know it all. We’re going to do the things we know need to be done, and sales can wait because they are not part of the strategy.

Now, when I walk into a new role, I’m working with the executive team and the GTM team to understand where we are, where we need to go, which motions will get us there, what we already have, what we need to build, and what we need to activate.

At the same time, I’m thinking about how we can get into market faster while we are building the operating structure we need.

I think sales appreciates that.

It starts with talking to them and listening. What do you think you need to be successful?

It is basic, but it also requires honesty.

Here is where I am. Here is how long I think it will take based on the budget and resources I have.

During those first 90 days, I will probably work twice as many hours just to put something in front of them so they can begin seeing traction earlier.

They appreciate that you are doing what you can to enable them and that you are not making perfect the enemy of good while you build the longer-term plan.

Brian Carroll: Could you share a lesson or a story about something you wish you had done differently, so someone else might avoid the same mistake?

Corey Livingston: If you’ve been in B2B marketing long enough, you probably have plenty of scratches and bruises from trying to align with sales.

The bigger the company, the harder it is.

I’ve worked at $10 billion companies, $200 million companies, $50 million companies, and $10 million companies. The smaller the company, the easier it is to align.

That is one reason I now like working in a certain size of company, where you can have more impact and where sales and marketing need each other, particularly during an active growth phase.

In larger, more complex companies, I’ve found it much harder to align. The business is more mature at $10 billion, so I’ll add that as context.

The other thing I’ve learned is that sales leaders at the top of the organization are not the only people who matter.

The mid-level sales leaders, the people the teams report to, typically the GMs and sales vice presidents, are often the people individual sales reps listen to first.

Brian Carroll: Mm-hmm.

Corey Livingston: I’ve had experiences where I had total alignment with the SVP of Sales or the CRO, but I was out of alignment with the next layer down.

In some cases, I’ve also worked in environments where sales simply did not want to align with marketing.

That is a broader issue in our industry. Marketing is sometimes not trusted or is seen as lacking industry knowledge. Marketers may be viewed as too focused on pretty colors and pictures and not focused enough on understanding the day-to-day work of the sales team.

In those environments, it is nearly impossible to be successful. Sometimes, you simply have to move on.

Brian Carroll: Mm-hmm.

Corey Livingston: In other environments, it is about continually building trust with the mid-level sales manager.

It is not just about focusing on the highest level of leadership. It is about working with the people in the trenches every day.

What are your objectives? What are you trying to achieve?

You also need to let them know you understand how sales works and ask questions that are not coming only from a marketing lens.

I have never carried a quota, unless you count marketing and selling fractional services, but I know enough because I have embedded myself in those organizations.

When I ask questions from the sales team’s perspective, such as, “Who is your highest-performing rep? Who is your lowest-performing rep? Where do you need the most help?” it helps me align much more effectively.

Then, again, it comes down to following through.

Brian Carroll: The big takeaway I’m hearing is that you cannot just align at the executive level. You have to move one, two, or three levels down to the frontline managers.

Corey Livingston: Yes.

Brian Carroll: Those are the people who see the day-to-day experience of the reps.

Corey Livingston: Yes. Not everyone is able to do this, and that is another reason I now align more with midsized companies.

I talk to reps one-on-one. What are they struggling with? Where do they think they need help?

Even in my current role, if one of my salespeople contacts me and needs help, I will drop what I’m doing to help them.

It is about understanding their world and understanding how they get paid.

As long as the request is aligned with the direction we have all agreed to pursue, those little touches matter.

Maybe you were willing to work an extra hour to help someone pull a list. I don’t care about my title. I will do whatever it takes. We’re all in this together.

That is what people on the sales team and the product team need to feel.

They need to feel that you are just as invested in their success as you are in your own.

Not everyone operates that way, but when someone sees that you are willing to jump in, even if it is just helping write an email or pull a list, it matters.

No matter your level in the organization, those small things go a long way toward building trust and creating alignment.

I will never stop doing them.

Brian Carroll: What I’m hearing is that you’re doing things that help reps have more effective selling time and add value to their day.

At the same time, you’re working on the strategic initiatives that will contribute over the long term while still meeting short-term needs.

Corey Livingston: Yes. It is similar to Maslow’s hierarchy of needs. People need oxygen. They need water.

I’m definitely securing my own oxygen mask, but I also have one to give the sales reps.

Even if I had something due and helping a salesperson was going to put me behind on a deliverable to the executive team, I would have no problem saying, “I need an extra hour or two, or an extra day. I need to help this salesperson. They have a deal on the line, or they need to increase their prospecting activity.”

I don’t think anyone would argue with that. No one ever has.

Marketers have to come down from the ivory tower and understand that, in B2B in particular, most organizations are going to be sales-led.

You have to accept that reality and not fight the system.

I’ve seen many B2B marketers try to fight it. They say marketing should be this or marketing should do that.

But at the end of the day, sales is the tip of the spear.

As long as we are aligned with the go-to-market strategy, marketing has to be the foot soldiers. We provide air cover, but we also need to be on the ground doing reconnaissance and whatever else sales needs to be successful.

That should happen not just at the organizational or academic level, but also one-on-one.

That is the attitude I encourage and look for when hiring people for my team.

Brian Carroll: How do you manage when several different motions are competing for attention? How do you decide what comes first and what has to wait?

Corey Livingston: Once you have the motions built, I’ll go back to something I said earlier: you can’t scale everything at once.

You have to return to the growth hypothesis and understand where you are in the lifecycle.

If you are in the build phase, it may take twice as much time, or even three times as much time, to reach the activation and scale phases.

This is not just a decision I make on my own. It is a decision made as part of the GTM team.

I may be facilitating or leading the conversation, but we all have to agree on where to place our bets in the short term versus the long term while we are building.

We also have to align the investment with those motions.

For example, when you don’t have an established brand in the enterprise, it will take time for buyers to understand who you are and for you to build credibility.

In that case, you might prioritize channel partners.

Large channel partners already have relationships. They serve as technology advisors to CIOs, CTOs, and other leaders in enterprise organizations.

The best short-term path may be to invest in building your partner ecosystem.

Make sure partners are aware of you and your capabilities. Attend their events. They are often the people who will recommend you.

It is rare for a CIO to come directly to a vendor’s website. They may conduct some research, but they are unlikely to fill out a form. That is not how their buying process typically works.

They also have many people prospecting them at any given time.

So you have to ask whether channel is the fastest path to revenue and what the tradeoffs are.

You may have to pay an agent commission in addition to the sales commission, so you have to balance that.

Could inbound be the priority? Inbound is not usually a strong enterprise motion, but you may need to keep investing in it to generate smaller deals while you build toward larger ones.

It really comes down to triangulating where growth will come from.

It could be retention and expansion. If that is the expected path to revenue, you need to assess everything around where you are in the lifecycle, what investment is required, what the timeline looks like, and how much budget is available.

It is like solving a Rubik’s Cube.

Once you decide, you have to get everybody on the same page and make sure the executive team is aligned.

That is what will be communicated to the board. They need to see consistency in the thinking and commitment to the plan.

Brian Carroll: As you measure the plan and its outcomes, I think many marketers treat pipeline as the main scoreboard.

But pipeline is really a lagging signal. It shows what has already happened.

Corey Livingston: Yes.

Brian Carroll: What do you trust as a leading indicator besides pipeline?

Corey Livingston: I trust engagement signals.

Whenever we are launching a motion, we are looking for good signals. We want to understand what is working before we double down on the investment.

I would not say I am risk-averse, but I am cautious.

During almost all of the 20 years I’ve worked in B2B marketing, budgets and resources have been constrained. That is simply the nature of the work.

When we are first investing in programs, I look at different indicators depending on the phase.

If we are in the build phase, the indicators are more about operational readiness.

What did we deliver?

If we are moving into a specific vertical, do we have case studies and references? Do we have thought leadership content? Do we have a dedicated web page? Do we have relevant experience?

Those indicators are more about completing the work we need within a specific period of time.

If we are in the activation phase, we now have enough assets and a minimum viable approach to launch into a specific segment.

You cannot get to pipeline without engagement.

If no one is engaging with you, looking at anything, responding on LinkedIn, responding to email, picking up the phone, or visiting your website, that is a sign that you may need to reassess the strategy.

You are not going to get to pipeline without engagement.

With account-based marketing, which is one of our motions, we look for movement among high-fit accounts.

We look at website intent. Are those accounts visiting the website? What are they doing? What does their search pattern tell us? Does it indicate active research?

We also look at partner-sourced engagement.

Are we getting meetings when we attend partner events? Are partners contacting us about opportunities? What is the quality of our inbound interest? Are people engaging with our content?

It is a great time to be a B2B marketer because you can measure almost everything and have so much visibility.

The challenge is separating noise from a meaningful signal.

Those are the things I look at, and they can be difficult to communicate when you are not yet in the scale phase.

When the motions have not been in market for long, you are trying to communicate progress before the final outcomes appear.

Most organizations, especially the C-suite, are highly outcome-oriented.

They want to know: How many opportunities are there? What is the value? What stage are they in? What is the commit? What is the best case? When will this close?

When you bring them engagement metrics, the reaction may be, “Okay, but what does that mean?”

You have to continually explain why those indicators matter.

Even when you are looking at lagging indicators like pipeline, you still need to work backward.

What are we doing? Are we focusing on the right accounts? Are we prospecting? Where are the leads coming from?

All of those things matter before you get to pipeline.

Brian Carroll: From your experience, are there any key indicators that tell you the company is moving in the right direction and making progress?

Corey Livingston: One of the things we look for is whether we are getting meetings.

Meetings are a major indicator.

To me, that could represent a potentially qualified lead. Is it a qualified meeting? Was there an outcome that led to a possible next step?

That is one of the most important indicators I look at.

There are other signals, such as opens, click-throughs, and whether the right accounts are visiting the website. Do they meet our ICP?

But meetings are one of the biggest indicators.

As you move into enterprise, I think you have to throw BANT out the window: budget, authority, need, and timeframe.

That is especially true when you are just beginning to enter enterprise accounts.

When the motion is early, the question I work on with sales is: Are we getting a meeting with the right person at the right account?

That is what we look at most.

Are we moving to the next step, and why or why not?

That tells us whether it was truly the right person or whether there may have been a product-fit issue.

It could have been a strong, qualified lead. It could have been the right person at the right account and matched our ICP, but perhaps something was missing in what we could offer, and the opportunity could not move to the next step.

That is still an important signal.

Brian Carroll: For someone in the trenches right now, what do you think most leaders get wrong during the first 90 days of a GTM rebuild?

Corey Livingston: I would say most leaders try to fix things too quickly during the first 90 days.

The first 90 days are really about diagnosis.

It may not take the full 90 days. It may take 30. But leaders often either take too long or jump in and try to fix things too fast.

The diagnostic piece is critical.

Listen. Interview every executive. Understand the situation from their point of view.

Many people struggle to answer a question I ask: What does marketing success look like at the end of 90 days or at the end of six months?

That is a very difficult question for many people to answer.

I don’t think that is a bad thing. It means you have an opportunity to shape how you should be evaluated and to educate the organization.

In many companies, when I do receive an answer, it is usually: How many leads did you produce?

But we all know marketing is much more than leads.

You are not going to generate leads if you do not have brand awareness and credibility.

I’m glad brand awareness and credibility are coming back into focus because they are incredibly important.

My advice is to spend time listening, interview the right people, and understand how they think about growth.

Try to surface any conflicting information that could undermine your approach.

If you find conflicting views, bring the people together in a forum rather than addressing it only one-on-one.

You can say, “Here are some things I heard that I’m struggling with. Can we have a conversation about what this means and how we can get on the same page? If we don’t, here will be the impact.”

I think that demonstrates thoughtfulness.

Once you do that, you can also tell the leadership team, “The sooner we align on this, the faster we can move.”

There may also be low-risk activities you can begin while conducting the diagnosis.

For example, in a recent company, we started doing LinkedIn outbound and testing our messaging.

We looked at who was responding. It was low-risk and did not require a large amount of messaging.

Those activities can contribute to what you are learning while you conduct the broader diagnostic work.

Once you have that picture, it becomes much easier for marketing executives to perform effectively.

They have spent time understanding everyone’s point of view, focusing on the areas of alignment, surfacing the areas where alignment is missing, and developing a solution.

That is when you are seen as a more strategic player at the table, but also as someone who can execute.

Brian Carroll: The overarching theme I’m sitting with is clarity and helping the collective team gain clarity together.

Corey Livingston: Most seasoned marketing or GTM leaders know that, but it is becoming a lost art.

I can’t tell you how many times I’ve stepped into environments where people were not talking to one another. They were talking around one another.

It is a skill, and a valuable one, to be the facilitator and the person who brings everyone together.

Brian Carroll: Corey, thank you. I appreciate you joining us today.

For our listeners, here is a question I would like you to take back to your own team:

Are you measuring what you built, or are you measuring whether it can get you where you are going?

Corey Livingston is the Vice President of Marketing at DartPoints. You can find her on LinkedIn.

Thanks again for listening, and thank you, Corey, for joining us today.

Corey Livingston: Thank you, Brian.

This version is ready to paste into the WordPress code editor beneath the show notes.

But those systems often miss the people, pressure, risk, trust, and hidden stakeholders shaping the actual decision.

In this conversation, Scott shares what he learned from studying more than 10,000 buyers across 15 industries, including why so many people who influence a deal never appear in the CRM, why B2B buying is more emotional than we admit, and how personality, culture, and hidden stakeholders shape complex deals.

The big question behind this episode is simple:

Even if our lead systems worked perfectly, would they really explain what drives a buying decision?

About this episode

In complex B2B sales, the visible buyer journey is often only part of the story.

The CRM may show one set of contacts. The real buying group may include several others.

The business case may look rational. The actual decision may be shaped by fear, trust, confidence, internal pressure, and personal risk.

Scott Gillum calls this The Hidden Buyer Journey. His research shows that many of the people who influence deals are never entered into the database, and many of the signals that matter most are not captured by traditional lead and pipeline systems.

Scott and Brian discuss:

• Why human-to-human selling still matters as AI and rep-free buying grow
• How one sales team nearly missed the real executive concern in a deal
• Why 85% of buyers in a buying group may not be visible in the database
• Why complex B2B buying is emotional, even when the process looks rational
• How personality and culture influence buying decisions
• Why empathy is not a soft skill in complex sales
• How sellers can use AI to become better with people, not just louder at scale

About Scott Gillum

Scott Gillum is the founder and CEO of Carbon Design, a marketing services firm focused on understanding buyer behavior and improving B2B growth.

He is the author of The Hidden Buyer Journey: How Personality, Culture, and Hidden Stakeholders Decide Your Deals.

Scott’s work focuses on the hidden forces that shape B2B buying decisions, including personality, buying-group dynamics, organizational culture, and the stakeholders who influence deals but often never appear in CRM or marketing automation systems.

Scott Gillum on LinkedIn

Chapters

00:00 Introduction: Scott Gillum and The Hidden Buyer Journey
01:06 The human-to-human selling relationship
02:15 When the CRM tells the wrong story
04:10 The 85% of buyers missing from the database
06:14 The emotional gap in complex sales
08:03 Buyer confidence versus vendor confidence
11:28 The two-thirds rule and personality-based selling
15:16 Why empathy is not a soft skill
18:18 How sellers should adapt under pressure
20:44 Using AI to move closer to the customer
23:42 Closing thoughts

A few things worth taking away

1. The CRM may not show the real buying group

Scott shared an example of a deal where the sales team thought the need was real-time project profitability. But late in the deal, the CEO’s behavior showed a very different concern: cash flow.

The visible activity told one story. The person with the most influence over the decision was telling another.

2. Hidden stakeholders are not a small problem

Scott said his team found that 85% of buyers in a buying group were not in the database. In one example, a company gave its team 100 contacts for an opportunity. After reading the email threads, they found nine people in the actual buying group, and only two of those nine were in the system.

That changes how we think about attribution, lead management, sales process, and account strategy.

3. Complex B2B buying is emotional because the risk is real

Scott put it plainly: buying the wrong iPhone may be frustrating, but nobody gets fired for it. Making the wrong million-dollar SaaS decision is different.

That risk creates pressure. And that pressure shapes how people make decisions.

4. Buyers need confidence in themselves, not just confidence in the vendor

One of the most important ideas in the conversation is that sellers often believe their job is to make the buyer confident in the vendor.

But in a complex sale, the buyer also needs confidence in their own decision.

They need to believe they can defend the choice internally, manage the risk, and survive the consequences if things do not go perfectly.

5. Personality and culture shape how people buy

Scott explains what he calls the two-thirds rule: certain personality patterns tend to concentrate in industries, roles, accounts, and buying groups.

That does not mean every person is the same. But it does mean sellers and marketers can get smarter about how different buyers process information, evaluate risk, and build trust.

6. Empathy is not soft. It changes outcomes.

Scott shared an example from email analysis where a seller who showed empathy and understood the buyer’s situation had a much better path through the deal than sellers who tried to drive the process harder.

In complex sales, empathy is not about being nice. It is about understanding the pressure the buyer is under and adapting accordingly.

7. AI should make sellers better with people, not just louder at scale

Scott’s warning is direct: we chose scale because we were not good at conversion.

AI can make that problem worse if it simply produces more outreach. But it can also help sellers understand buyers, buying groups, and corporate culture more deeply.

A few lines that stuck with me

“We have a tendency to make purchase decisions emotionally, and we rationalize them later.”

“You buy the wrong iPhone version, you’re not going to fire yourself. You make a bad decision on a million-dollar SaaS implementation.”

“Turns out they’re not putting the people in.”

“Titles and roles don’t make decisions. People do.”

“We chose scale because we weren’t good at conversion.”

“We train on tools. We don’t train on buyers.”

Resources mentioned

• The Hidden Buyer Journey: How Personality, Culture, and Hidden Stakeholders Decide Your Deals
• Scott Gillum on LinkedIn
• Carbon Design

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Thanks for listening.

Transcript

Brian Carroll: Welcome to The B2B Roundtable: What Dashboards Miss. I’m Brian Carroll, and here’s the question behind today’s conversation.

Even if our lead systems worked perfectly, would they really explain what drives a buying decision?

My guest today is Scott Gillum. He’s the founder and CEO of Carbon Design and the author of The Hidden Buyer Journey.

Scott spent seven years studying more than 10,000 buyers across 15 industries. And here’s what he found: we’ve gotten very good at tracking what buyers do, but we still don’t understand enough about the person making the decision.

Because the real buyer journey often happens somewhere our dashboards can’t see.

Scott, welcome to The B2B Roundtable.

Scott Gillum: Thank you, Brian. It’s good to be on. It’s good to talk to you again. It’s been a few years, so I’m excited for our conversation.

Brian Carroll: You’ve described four selling relationships in the book, and you said the human-to-human one is disappearing. What are we losing right now?

Scott Gillum: I think it’s a value equation.

In the book, we talked about the number-one driver of purchase decisions being trust and reliability. So if the tools advance to be more trusted than the human, and you already see some of that in the research where buyers want a rep-free experience. They’re well through the buying process before they talk to a rep, if machines can do a better job of giving information and conveying that to be credible, and the audiences trust those sources, they’re going to do it.

This is an opportunity. The book is really about how we elevate this human-to-human selling experience so we can preserve the most important thing, which is the human connection, when it comes to making a purchase decision in B2B.

We have to take a hard look at how we’re training our reps, the information we’re enabling them with, and whether we really understand the buyers at the other end of the deal.

Brian Carroll: I wanted to talk about a deal where the CRM told one story, but the people inside the decision were telling another.

Scott Gillum: It’s in the enterprise space. It’s a SaaS company. The sales team was hearing one thing from the buyers they were having conversations with, and they thought the need was around real-time project profitability.

Their system is an ERP system. It was focused on project work. Fortunately, they had put all the buyers they were dealing with into their database, which isn’t common.

Two weeks before the final presentation against the incumbent competitor, the CEO began showing signs of activity. His intent signals were throwing off cash flow. He searched for cash flow 35 times over the last two weeks.

So we brought that information to the account team before the final presentation. They had already crafted the presentation around project profitability. I’m like, “Why are you on project profitability? He’s on cash flow. What is going on here?”

This was a fast-growing company. They were burning through a lot of cash. We had to make the connection between the real-time profitability view and cash flow, and how their system was able to do that.

A lot of times, buyers aren’t telling you what the real need is because they don’t really understand it. They’re just told to go look for things. Then, when you get down to the key decision maker, he has a very specific thing he’s looking for: how can you get greater visibility into cash flow?

That was picked up through intent signals because they had put that contact in the database. When he hit a form, we could track his activity and bring that information back over.

The unfortunate thing is, when we looked at this, 85% of those buyers in a buying group aren’t in any database.

Brian Carroll: Tell us more about this 85%.

Scott Gillum: It was one of the biggest discoveries. For 20 years, I’ve been working with clients on marketing attribution. Why can’t we connect these assets we’re developing to deals? It was always this big mystery. Maybe the salesperson just didn’t put the information in the system, so we can’t track it back.

Turns out they’re not putting the people in.

We discovered this by reading emails between the reps and the buyers. We did it over five organizations, ten deals, end to end. This was a lot of data, a lot of emails going back and forth.

What we discovered was that 77% of the buyers in the buying group enter late stage. They enter during trial, demo, and final presentation.

The sales rep’s behavior is to get everything set up for the trial, get the paperwork, get the MSA, get the tech team ready. They don’t take time to enter those buyers. They keep their primary contact in the database because they need that person to open the opportunity, but all these other people are showing up and influencing deals.

Clients would give us all their contacts for an opportunity. Let’s say they gave us 100 contacts. Then we read all the emails and found nine people in the buying group. When we cross-referenced that, only two of the 100 were actually in the buying group.

Brian Carroll: What’s getting in the way of people doing this?

Scott Gillum: It wasn’t until we started reading the actual emails between the sales reps and the buying groups that we could see this.

It’s about having access to see where the hidden buyers are. Now we can fix that. We have a lot of different ways to fix that, and they’re sitting there.

Brian Carroll: You called this an emotional gap. What does this gap look like inside of a purchase? With complex sales, buyers still require technical evaluation, procurement, financial approval, and a business case. That all seems rational. Tell me more about this emotional gap.

Scott Gillum: We have a tendency to make purchase decisions emotionally and rationalize them later. That’s been true in B2C for a long period of time, and I was involved in research about ten years ago that showed that’s the case in B2B buying as well.

The reason is the risk equation.

You buy the wrong iPhone version, you’re going to be upset with yourself, but you’re not going to fire yourself. You make a bad decision on a million-dollar SaaS implementation, and there’s high risk involved.

We forget that risk. We also forget this is a person in a role, with a persona in that role, sitting inside a buying group, inside a corporate culture, inside an industry. All those things add pressure to the decision maker.

We know this is true because we sit inside organizations and see how we operate every day when trying to make decisions. But we never consider that equation when selling something.

It all exists. It influences people. People make decisions very selfishly, too. Depending on your personality type, you have different motivations for your behaviors. In the past, we didn’t have the tools to pick up those signals. Now we do.

Brian Carroll: We think our job is to help the buyer have confidence in us, when what we really need to do is help them have confidence in themselves.

Scott Gillum: Yes. It’s the pressure. It’s the risk involved. How do we help an individual or a team of individuals? Typically, what we found is that three or four people drive deals through organizations.

How do you give that small group confidence and trust? How do you convey trust?

When we looked at purchase drivers, buyers identified things like product, reliability, and product utilization. But all of those factors are realized after the decision. So something else is being conveyed before the decision.

That something else is: I feel confident in this provider. I feel like I can trust them. I feel like this person is credible. I feel like this company is credible. I like their reputation.

That’s what drives purchase decisions. It’s not just the feature functionality of the product, because that’s realized after the decision. Most buyers don’t trust your ROI. They don’t trust your case studies. It’s very rare that any vendor can repeat the same results in that company.

There is something else going on. We know that to be true, and I want people to be conscious of it.

Brian Carroll: Why do you think we have that gap around understanding the emotional side of complex sales?

Scott Gillum: It’s difficult to manage. How do you teach a rep to manage someone’s emotional decision-making? It’s hard.

That’s one reason I try to make this easy to understand through personality types.

At the industry level, there’s the two-thirds rule. People flock together in industries and roles. They have similarities. How you choose a degree in university is often driven by your personality type. That degree takes you into a role where you find similar personalities. That role puts you in a company or industry where certain personalities flock together.

One example is the airline industry. Half the people working in the airline industry are in operations. This is an industry where planes can’t drop out of the sky. It has to be data-driven, analytical, and detail-oriented.

There is a personality type that matches that: the Conscientious personality type in DISC. As a result, you find that 65% of people in those roles skew toward Conscientious.

Depending on the company and how much efficiency matters to the business model, you will find more Conscientious types. There’s a certain logic to it.

That’s often the feedback I get when people read the book: it’s perfectly logical. Why aren’t we doing anything about this?

At the industry level, company level, and group level, I’m trying to make it easier to incorporate this into everyday activities.

Brian Carroll: You just talked about the two-thirds rule. What does that change in practice, and how did you come up with it?

Scott Gillum: That took seven years to figure out across the fifteen industries.

When we started doing this, we started at the persona level. A client came to us and said product marketing had handed the go-to-market team 17 personas. How do we action that? It was impossible. What it really was, was 17 different selling scenarios.

We said, let’s look at your audience and profile them.

We took an AI personality profiling tool that was built for recruiting and used it to understand the personality types of buyers. We started seeing similarities at the role level.

The first thing we looked at was data scientists. Two personality types made up 90% of that role. If you know that, you can customize language for those buyers.

Most of the research showed that one personality type will be at least 50% of the audience. That’s true at the role level, account level, and industry level. So you can aim personalized content at half of your audience, and I mean deep personalization.

You can take the insights around DISC and train AI content generators to write in the language of those buyers. We have built custom GPTs to do this.

You can take one email and make it truly personalized by putting it in the language of those buyers.

In the book, I give an example where I take an old IBM Selectric ad, adapt it for today, and then change it by personality type. You can see how the language changes based on buyer preferences.

We now have the ability to do highly customized outreach.

Brian Carroll: What difference can it make? Why should people invest in this? What have you found when you’ve run campaigns or outreach using this?

Scott Gillum: It impacts every level: response level, engagement level, conversations.

There are examples in the book of companies that used this to set up weekly conversations and to build personas in ways that helped with client retention.

Role-based personas give you the professional view of a person in a role: title, responsibilities, and the typical things. But if you add the personal side, you get something more useful.

One example is CISOs, chief information security officers, in cybersecurity. These people are highly technical, but we forget they’re also highly emotional. The amount of risk they manage is enormous. I don’t know how they sleep at night.

We told a company selling cybersecurity solutions that they were not addressing the raw emotions of this buyer and the pressure they face every day inside the organization.

If you combine the business language with the personal language, you have an opportunity to separate yourself from the crowd. You can change your language and messaging to be more empathetic, build credibility, and build trust because you understand their situation.

It makes a huge difference.

Brian Carroll: Some people think empathy is not something we need to focus on. They see it as a soft skill that doesn’t necessarily have a place in business. What do you say to that?

Scott Gillum: I say BS.

When we were reading emails, we were watching seller behavior. I saw two dominant personalities, two Northeast dominant sellers, selling to a Midwest Conscientious buyer, and it was not going well.

I also watched a female seller from the South selling into a West Coast company. Her tone and empathy stood out. One of the buyers she was dealing with had been out for surgery, and she opened by talking about the recovery and hoping she was doing well.

This is a small sample size, but there was much greater success and a shorter sales cycle with the person who showed empathy and understood the buyer’s situation inside the organization.

The other sellers were just driving the deal. They were nonstop driving. You could see the buyer on the other end starting to tune out. The communication started to gap. They weren’t responding.

Watching that play out in real life, you could see that this buyer didn’t really want to engage with that kind of seller.

Brian Carroll: From the perspective of a leader listening right now, what should they have their team do differently on their next five accounts?

Scott Gillum: First, go get an AI personality profiling tool. They’re not expensive. They’re effective for BDRs and SDRs, the people who initially have contact with customers. They’re also helpful when closing the deal.

Start by assessing yourself. That’s the most important thing. Then assess the people you’re going to talk to. Some tools show your attributes versus the attributes of the people you’re talking with, so you can adjust your style.

One of the chapters is called “The Sales Chameleon.” We give an example of Ben, someone we found in the research. He is something different in each company, but he knows where his value is.

Understanding your value and being able to adapt to the buyer, the situation, and the organization makes a world of difference.

That’s the future of a salesperson: someone who understands how to convey value, but do it in different ways.

Brian Carroll: How do we get people to start acting this way? People are nodding and saying, “This sounds great, but I need to make my number.” What do you suggest they do?

Scott Gillum: There are no other technologies that are going to fix us from a scale-volume perspective. They’re beyond the top of the yield curve. They’re declining. You’re starting to see consolidation in the tools.

This is no longer about throwing a wide net and seeing what you can drag back. This is about how I do better with what I have. This is about conversion now.

Every deal is precious.

Your buyers do a lot of research on a solution. How much research are you doing on your buyer?

Opportunities are going to be smaller, precious, and fewer. How do I convert them at a higher rate? You do that by understanding the person on the other side of the deal as a person, not as a title or role.

Titles and roles don’t make decisions. People do.

You have to understand that person, their situation, their role, and their organization. You have tools to do that, but you also have to put in the time and do your homework.

Either you use the tools to enable you to become a better seller, or you use the tool to replace you. That’s where the investment is going. There is far more investment going into sales technology than sales training.

Brian Carroll: Right now, AI gives us the ability to scale outreach. But unless we really understand our buyer, all we’re doing is hurting ourselves.

Scott Gillum: We chose scale because we weren’t good at conversion.

We train on tools. We don’t train on buyers. Those days are over.

Most of your market is not in-market. If you are lucky enough to capture someone who is in-market, you better do a really good job with them. You better get to a close.

It’s time to invest in people learning how to be better with people.

Brian Carroll: What can we do right now so that we’re using AI in a way that moves us toward the customer? You’ve already talked about using tools that help us analyze personality. How else?

Scott Gillum: This is what I call a hack. It’s so simple, and we should be doing it.

You can understand corporate culture and decision-making without ever talking to anyone. Before you even approach them, you can understand how they make decisions and how fast they make decisions by understanding the corporate culture.

Take the senior management team. Culture rolls down from the top. Profile that senior management team, and you will learn their priorities and how they make decisions.

One company we profiled was a construction company, a top 50 Fortune 500 company. Twenty-one out of 22 executives we profiled on their website had the same personality type. They had different backgrounds and experiences, but the same personality.

You knew immediately this was a dominant organization. It was a driven organization.

Once you understand that, you can align your messaging. Dominant personalities want to see use cases and case studies that are as similar as possible to their organization. They want to see the outcome. They want to see return on effort.

That is how you approach them with your messaging and value proposition. It is sitting right there. All we need to do is harvest it.

Brian Carroll: What are the nuances?

Scott Gillum: Education is fascinating. You can go into LinkedIn, go into the company section, look at people, and then look at the education of the people who work in those companies. You can see the top degrees.

If a company has a certain personality, say Conscientious, you’re going to find engineering degrees and science backgrounds. It makes sense. If you’re dealing with a company that has a lot of scientists, like R&D, you’re going to have a distinct personality type.

What we learned is that the more advanced degrees you have, the more likely you are who you are as a person. If you’re happy in your role and your job, there’s a reason for it. Your background and personality have led you down that path.

If you’re fortunate enough to match that, you’re probably happy. If you’re not happy in your current position or job, there’s probably a mismatch between who you are as a person and either the organization or the role you’re in.

Brian Carroll: Scott, this has been a fascinating conversation. I’ve learned so much talking with you, and I know our listeners have as well.

This has been Scott Gillum, founder and CEO of Carbon Design and author of The Hidden Buyer Journey.

Our systems can tell us what the buyer did, but they don’t often explain what the buyer feared, what they trusted, or what they needed from the people selling to them.

Scott, people can find you on LinkedIn. We’ll put the link to your book, The Hidden Buyer Journey, in the show notes.

Thanks so much for sharing your insights with us. I really appreciate you being here today.

Scott Gillum: Thank you, Brian. I really appreciate it.

Here’s something most B2B marketers know but do not always say out loud.

We have gotten very good at measuring things.

Attribution. Pipeline metrics. Sourced revenue. Influenced revenue. Cost per lead.

And yet, a lot of B2B brands are still forgettable.

Not because the marketers are bad.

Because the system keeps pulling them toward what can be tracked, reported, and defended in the next pipeline review or board meeting.

That is the tension at the center of this conversation with Lindsay Cournoyer, Fractional CMO and Brand Marketing Consultant at LC Consulting, and former CMO at Blue J.

Lindsay has led marketing at companies including Axonify, Coconut Software, and Blue J. At Blue J, an AI-powered tax research company, she helped 5x revenue and raise $122 million in Series D funding.

But that is not the main reason I wanted to talk with her.

I wanted to talk with Lindsay because while that growth was happening, she made a brand bet that many B2B marketers would struggle to defend on a dashboard.

She invested in out-of-home advertising.

Billboards. Elevator ads. Radio. Physical media in a B2B SaaS company.

That is not the usual B2B playbook.

But Lindsay believed the company needed something that the usual performance channels were not delivering: awareness, trust, and memory in buyers’ minds before they were ready to enter a sales process.

Her line from LinkedIn captures the problem clearly:

“B2B brands are so obsessed with being measurable that they forget to be memorable.”

That is where this conversation starts.

We talk about why performance marketing can capture demand but cannot create all of it, how Lindsay made the case for out-of-home inside a B2B SaaS company, what she measured before and after the campaign, and why brand work can feel risky when marketing already has to justify itself more than other functions.

If you have ever felt pressure to optimize for a metric instead of an outcome, this episode is for you.

About Lindsay Cournoyer

Lindsay Cournoyer is a Fractional CMO and Brand Marketing Consultant at LC Consulting.

She has led marketing at B2B companies including Axonify, Coconut Software, and Blue J, where she most recently served as CMO. At Blue J, she helped the company grow revenue 5x and raise $122 million in Series D funding.

Lindsay works with B2B SaaS founders and leadership teams on brand strategy, messaging, and go-to-market.

Connect with Lindsay

Connect with Lindsay Cournoyer on LinkedIn

Chapters

00:00 Introduction: B2B Brands Are Too Measurable to Be Memorable
01:53 Why Brand Has to Create Demand Before Performance Captures It
03:29 The CEO Saw the Brand Problem
04:24 The Marketing Tax and Why Brand Needs CEO Support
07:35 Making the Case for Brand Inside the Business
10:11 How Lindsay Measured Awareness and Consideration
13:50 Staying Steady When the Bet Feels Risky
16:55 What to Do When Your Company Doesn’t Value Brand
22:26 How to Make the Case for Brand Investment

A few things worth taking away

Performance marketing has a role, but it mostly captures existing demand. Brand helps create the demand performance later captures.

B2B buyers need to remember you before they are ready to buy. If you are not already planted in their mind, you may never make the shortlist.

Out-of-home can be targeted in B2B when you know where your buyers work, commute, gather, and pay attention.

The marketing tax is real. Many marketing leaders spend too much time justifying their function rather than doing the work that creates long-term value.

A CEO who understands brand changes the entire marketing environment. Without that support, big brand bets are much harder to make.

Brand can be measured, but not always through the same dashboard logic as demand generation. Lindsay used pre- and post-campaign surveys to measure awareness, perceptions, consideration, and likelihood of purchase.

A brand campaign can move more than awareness. In Lindsay’s case, they saw an increase in awareness and purchase consideration.

Sometimes the best thing a marketer can do is accept the reality of where they are, protect their sense of worth, and look for a better environment where marketing is understood.

If a CEO does not understand brand, use examples from their own life. Show them how brands earn memory before the buying moment.

Sometimes you have to earn the right to make a brand investment by first showing how marketing contributes to pipeline and revenue.

A few lines that stuck with me

“B2B brands are so obsessed with being measurable that they forget to be memorable.” — Lindsay Cournoyer

“Marketing’s true job is to carve out that place in your buyers’ brains.” — Lindsay Cournoyer

“We have to build brand awareness and trust and credibility before you really step on the gas of performance marketing.” — Lindsay Cournoyer

“There are companies out there who actually get it. They are very hard to find, but they are out there.” — Lindsay Cournoyer

“Sales have to be there. And then you may get the shot.” — Lindsay Cournoyer

Resources mentioned

The B2B Roundtable episode with Jon Miller on what comes after the MQL

Growth Isn’t a Headcount Problem. It’s a Precision Problem, with DeAnna Ransom

Listen and subscribe

Subscribe to The B2B Roundtable wherever you listen to podcasts.

Transcript

Brian Carroll: Here’s something most B2B marketers know but don’t say out loud.

We’ve gotten very good at measuring things: attribution, pipeline metrics, sourced revenue, influenced revenue, cost per lead. And yet, a lot of B2B brands are forgettable.

And it’s not because the B2B marketers are bad. It’s because the system keeps pulling them from what they know is the right thing to do, and they’re forced to do things that are tracked, measured, and can be reported at the next board meeting.

It’s harder to attribute when you focus on brand. It’s harder to justify in a pipeline review, so it often gets pushed aside.

Welcome to The B2B Roundtable. I’m Brian Carroll. And in this podcast, we talk about the things that dashboards miss.

My guest today is Lindsay Cournoyer. She’s been a marketing leader at companies including Axonify, Coconut Software, and most recently served as the CMO at Blue J, which is an AI-powered tax research company where she helped 5x revenue and raise $122 million in Series D funding.

That’s impressive, but that’s not the main reason I wanted to talk to her.

I wanted to talk to Lindsay because while this growth was happening, she made a significant investment in out-of-home advertising. And this included billboards, physical media in a B2B SaaS company. It was the kind of bet that’s hard to defend with a dashboard.

And she did it anyway.

So today we’re going to talk about why. And if you’ve ever felt pressure to optimize for a metric instead of an outcome, this conversation is for you.

And Lindsay has a line that names the problem really well. She wrote this in a recent LinkedIn post: B2B brands are so obsessed with being measurable that they forget to be memorable.

And that’s where we’re starting today.

So Lindsay, what were you seeing that made that feel true?

Lindsay Cournoyer: Yeah, it’s a great question. And I will say the obsession is real among executives and board members.

I think back to what Jon Miller talks about all the time, that people want marketing to be a gumball machine and act like a gumball machine. You put a dollar in and you get three out. And it’s supposed to be this really predictable thing that you can just game the system and get to the revenue that you want.

But that’s just simply untrue.

Performance marketing has its place. Its role is to capture the demand that’s been created for your brand. But if you just lean into performance marketing and focus on that, you’re missing the whole front part.

Really, what I believe is marketing’s true job is to carve out that place in your buyers’ brains and be the solution that comes to mind first when a buyer thinks of your category.

And if you don’t focus on building your brand and trust and reputation before you get into performance marketing, you’re really missing the whole point of what I think marketing is here to do.

Brian Carroll: You made this significant out-of-home investment, which is unusual in B2B. That’s not something people typically do. And it was a big bet.

What was the problem you were trying to solve that the usual marketing metrics and channels weren’t solving?

Lindsay Cournoyer: Yeah, it’s another great story.

Really, the reason I took the role is because the problem to solve was named by the CEO in my interview process. And it was, not enough people know about us and the awesomeness that is our software.

It’s like, we have this great product, but the CEO knew that if everyone in the market didn’t know about it, the company was not going to get where they wanted to go.

So he inherently understood the need for brand.

I was winning already out of the gate. And like I said, that’s really why I took the job in the first place, because of that understanding of the need to build brand awareness and trust and credibility before you really step on the gas of performance marketing.

Brian Carroll: It sounds like your CEO was enlightened thinking about this idea of brand, because that is not the experience that a lot of B2B marketers have.

Lindsay Cournoyer: Yes.

I think we undergo a lot of scrutiny in marketing that other departments just don’t feel. We’re continuously having to justify ourselves and our decisions and our plans and our budget and our headcount.

And there’s just this kind of skepticism around marketing that exists. It’s pretty pervasive. It’s not in every company, but I’d say it might be in most.

It’s really tough to operate in that kind of environment and carry that kind of tax.

I have experienced it, and it really does just tire you out and take you away from the really important work that you should be doing when you have to be doing PR for your team all the time.

This was a brand new product. It didn’t exist. It was AI for tax research, essentially a ChatGPT-like experience where you go in and ask your tax question and up pops the answer with all the verifiable sources.

It didn’t exist before. And it was a much cleaner and more enjoyable way to do tax research than what accountants have dealt with in the past, with hours of painstaking research and judgment calls and asking the partner.

It just didn’t exist.

So the CEO really knew this is brand new to the market. We need to go introduce it to the market.

I am grateful for that, but I realize it’s not the case in every company.

So I do think, unfortunately, we do have to do some explaining about brand and why awareness matters and why building trust and credibility with buyers matters.

Really, I think CEOs should be curious about brand. If they’re not, that’s a mistake. They should take it upon themselves to go and talk to their marketing leader and really start to do their own research and understand why awareness building and credibility and trust is so important.

That shouldn’t always be on us.

So I would encourage any CEOs out there listening who don’t know a lot about brand or marketing and kind of see it as this black box, to really make an effort to understand the craft and the strategy behind it.

I think in certain cases, there are just CEOs or executive teams or boards out there who aren’t going to do that. And if you find yourself in one of those companies or situations, unfortunately, sometimes you just can’t get through and win, and you will just carry the tax ongoing.

Brian Carroll: That’s the double burden. You have your job to do, and then there’s the need to justify the very existence of the function or your team, and you’re constantly doing PR.

Lindsay Cournoyer: Yes. Yes. Yes.

Brian Carroll: How did you get there? How did you make that case?

Lindsay Cournoyer: I really did something that we all do a lot of. I had to essentially act kind of like a professor on brand.

I created a really detailed brand strategy deck that I presented at an executive offsite planning meeting. And I explained that we have to carve out a place in people’s minds as the category leader and a new solution that they can trust, and that we are already leading the category and are really the horse that they want to bet on.

So I went through quite an extensive educational exercise with the team, and the response was really positive.

These are people who really didn’t know that much about marketing, and they leaned in and they were super excited.

At the end of that presentation, I went through all of the things you need to do to build brand and credibility and trust and get that place in people’s brains.

And the culmination of that work was an out-of-home campaign and a big multi-channel brand campaign that was tremendously successful.

So I had the support of the internal team, which was amazing. But I will tell you that there were skeptics.

One of our board members was not happy with my campaign idea and expressed their displeasure. And, of course, our CEO was a little like, “Are we doing the right thing?”

And I just stayed steadfast. Yes, we are doing the right thing.

Their argument was that this was too broad, it’s not targeted. But actually, out of home can be very targeted.

For example, where are the offices of the firms you want located? They’re in specific cities or specific areas or specific neighborhoods. Go buy out of home and put a billboard right out front of their office or in the elevator that they ride up and down every day.

It’s really about getting their attention through an untraditional channel, but I think it’s a myth that it can’t be a targeted play.

Brian Carroll: It’s really interesting.

I was just thinking about when we had Jon Miller on our podcast earlier. We talked about the problem of the MQL, that it’s the last 5% of people who actually express interest.

But what about the 95% who don’t, who aren’t yet in consideration, who don’t quite even know the problem?

And as you talked about, you’re introducing something new, a new category, something that didn’t exist.

After it launched, how did you know it was working? What did you measure? What changed? And what did you have to admit you couldn’t measure? And so you needed to build that trust with the internal team to say, “Yeah, we’re still doing it because it’s the right thing.”

Lindsay Cournoyer: Yeah. Well, there actually is a very clear way to measure awareness. And it’s not cheap. You have to put some money behind it.

But what we did is we developed a survey, which we took to market through a third-party partner. And it basically asked people, have you heard about us? What do you think about us? Who do you see as the category leader?

Are you going to consider buying software like ours in the next year? Which product are you leaning toward?

So we asked a lot of what I think were smart questions just to understand current awareness and perception levels in the key markets that we wanted to win.

What came back was really interesting. Our awareness was actually quite high. We had done a really good job spreading the message and the product through events and partnerships. So we were starting from a strong place already, which I think was surprising to some of us.

But we came out strong, and we did a three-month campaign in four key markets where we used out of home and radio, which is another underutilized channel.

Accountants love radio. They listen to sports talk, and we did SiriusXM. It was a great channel to reach them.

Then we let the campaign go. And afterwards we went back and surveyed again.

The goal that we were going for was a four-point lift in awareness, which is statistically significant. We could say, okay, this campaign worked.

And we got much more than that out of the campaign in the results that came back.

And then, interestingly, this was amazing. Not only did the awareness lift in a big way, but consideration also moved.

So people who had seen three to four versions of the creative reported a much higher likelihood of buying us.

That was all I needed.

We worked so hard on this. And to be honest, I was scared shitless running this campaign. It was a big bet. I was freaking out. My agency had to calm me down several times because I’m like, this has to work. This is really important.

And they assured me, “Lindsay, it’s going to work. It’s going to work.”

And it did.

The outcome was so amazing that, since I have left to work for myself again, they’re going to keep going with the brand investment because it’s something that worked and it needs to be sustained.

Brian Carroll: I think a lot of marketers are dealing with similar feelings. They’re overwhelmed. There’s anxiety because they constantly have to justify their job. There’s constant input given from peers.

You wouldn’t tell the CFO, “Hey, have you thought of this ratio versus that ratio?”

Lindsay Cournoyer: Exactly. Yes.

Brian Carroll: What are some of the things you’ve needed to do to help yourself stay steady when every day people are wondering, why do we have marketing?

Lindsay Cournoyer: You know what? I honestly felt like this campaign was big enough and high profile enough that my job was on the line.

If it didn’t go well, there’s a high likelihood that I may be exited because it was a lot of money and a big swing and a big bet.

Like I said before, I was terrified. But I know this kind of investment is so important, and I believe in brand marketing through and through.

So I really had this internal dialogue in my head of, “You know what, Lindsay? This is the right thing to do. Don’t go down the death spiral. Just keep positive that it’s going to work.”

And the creative was really strong, super resonant.

Somehow I stayed positive and I believed in the campaign. And to be honest, if I lost my job over it, I would have been fine with that.

Brian Carroll: And so I’m just wondering if you were talking to someone else who is a CMO right now, as a peer or someone who wants to ascend to that role, what advice would you give them to be able to stay steady as they’re making these big bets and doing things that don’t show up in the dashboard right away, like you just did?

Lindsay Cournoyer: My advice is if you find yourself in a situation where you have a CEO who understands the value of brand, they’re going to let you take a swing like this. And they’re going to support you as they should.

If you’re in a company where the CEO doesn’t get brand or why it’s important, you’re likely never going to get the go-ahead to do something like this ever.

So I would say, when you’re interviewing for a role, and if you believe in brand and want to take a big shot like this, you really have to do your due diligence and go deep on the CEO you’re working for and the board and how they perceive marketing and whether or not their portfolio companies are doing stuff like this.

Because if you see that they’re not and all they care about is performance marketing, I think that’s a really clear telling sign.

Brian Carroll: I think there’s a lot of people who are listening who are like, that sounds great, but I’m where I’m at right now.

And maybe because there is this anxiety in the field of marketing, especially technology marketing right now with the rise of AI, with the questions about how buying is changing right now, and how we no longer can put forms up and do content marketing the way that we used to.

So I’m just wondering, for that person listening right now who wants to influence their team and they’re stuck in this tactical role of seeing marketing as the demand gen function only, what advice or suggestions would you give?

Because maybe some people are where they are and they’re saying, “How do I influence or even try to make a difference in my organization?”

Lindsay Cournoyer: The first thing we have to acknowledge is just sometimes you can’t make a difference.

And it’s up to you.

The truth is a lot of us just need jobs and income to support our families. I had this conversation on LinkedIn. Lisa Adams posted this exact comment on the post about the tax. Sometimes we don’t have a choice. We have to work in these companies that don’t get it.

I think you can either just accept it and do your job and earn your paycheck, but you can’t let it suck your soul.

You have to be able to say, this is the situation, and detach yourself from it to continue to work in the company.

But if you can detach and just do the best job and collect your paycheck, it sucks, but a lot of people do operate that way because we have to. We don’t have a choice.

At the same time, I would start looking at the brands who are doing out of home and who are doing brand activations. Start to network with their marketing team people. Follow them on LinkedIn and engage with their content.

You can work your way into a better situation eventually.

Brian Carroll: I think for some people, just that encouragement you gave could give us license to say, accept the reality where you are, but also open your eyes and don’t let that determine what your worth is.

Don’t let that steal or take you down that downward spiral.

Because I think a lot of people are in situations where they don’t feel that marketing is valued. And therefore then they are like, “Well, then I’m not valued.”

And what you’re saying is, no, there is a way out.

Lindsay Cournoyer: There is a way out.

There are companies out there who actually get it. They are very hard to find.

I’m working with a client right now where the CMO actually started in marketing. His first business was marketing services for a particular industry. And he gets it.

He’s taking these big brand swings. He just gave away a Tesla at a conference to draw people into the booth. It was amazing.

He’s leaning in and he’s super interested and he wants to input on strategy and jam on brand and marketing.

He’s like a unicorn. And they’re hard to find, but they are out there.

And when you find one, marketing becomes fun again.

I am having more fun working with him than I’ve had in quite some time. He just gets it.

So they do exist.

Brian Carroll: I like that phrase, fun. How can we get marketing back to fun? And what drew us to it?

A lot of people, I don’t know about you, but I didn’t go to school aspiring to move into B2B marketing. It was something I fell into, and then I just loved it because I love the complexity. I love the learning. I loved that there’s a variety of things.

Yes, you can get specialized, super specialized, but at the same time you have to have a bigger, more strategic view of things.

What are your thoughts on this?

Lindsay Cournoyer: I also didn’t know I wanted to be in B2B marketing, but I love it for all the same reasons that you do.

And it’s interesting. Again, in the post that I just wrote about this tax that marketers face, Chris Walker actually commented on it and said, this exists in tech, PE, VC-backed companies. And if you go work in a different industry, it’s a totally different game.

So that really got me thinking.

We all want to be in tech and we all want to be in SaaS. It pays well and it’s fast-paced. It can be fun. It can be brutal.

But what about thinking about other industries?

I was just contacted by a potential client whose business is in rocket science. And I was just like, my God, this is fascinating. How cool would it be to work on something like that?

Totally different.

So maybe another part of it is going to work in a different industry.

Brian Carroll: I wanted to ask to close, if a CMO or VP of marketing, a marketing leader, has an hour with their CEO this week to make the case for brand investment, what should they say? What advice would you give them?

Lindsay Cournoyer: I always like to bring it back to an example that they themselves will see themselves in.

Think about buying a new car. You want an electric vehicle. You’re going to look at Tesla, Polestar, I don’t know, all the other brands that now make electric vehicles. But when you think of electric vehicles, you think of Tesla first.

They own the category.

There you go. There’s the example of how they’ve done well because they are planted in people’s brains.

If you’re buying an EV, you’re buying a Tesla. Now there are more options, and we won’t get into the Tesla thing, but bring it back to an example and a scenario that they themselves have been in.

I think I’ve seen then the light bulb go on.

Brian Carroll: And if they’re proposing an idea or a bet, any thoughts you have on perhaps the smallest version of a bet if someone wants to move in this direction, but they haven’t won the credibility or trust yet to make that big bet?

Lindsay Cournoyer: I hate to say it, but sometimes you have to show results from performance marketing.

Be able to tie your activity to pipeline generation and revenue. And I feel like once you can clearly make the tie of how marketing is impacting on the revenue front, that really sometimes opens up the territory of brand.

Brian Carroll: Really good.

I think for people, we still need the big picture of what’s the impact we’re making on revenue, pipeline contribution, and using that as the basis to make the investment for things that aren’t going to show up in the dashboard.

What you’re saying is you’ve got to start with the dashboard, right?

Lindsay Cournoyer: Yes. Sales have to be there. And then you may get the shot.

And that’s what happened with me. I feel very grateful that I got to do a campaign like that.

Brian Carroll: Well, Lindsay, this is exactly the conversation I hoped it would be.

And for our listeners, if you have more questions or follow-up for Lindsay, Lindsay is doing work right now as a fractional CMO and brand consultant with LC Consulting. She works with B2B SaaS founders and leadership teams on brand strategy, messaging, and go-to-market.

If this episode was useful, please subscribe to The B2B Roundtable wherever you listen to podcasts.

Thanks again, Lindsay, for this great conversation.

Lindsay Cournoyer: Thanks so much, Brian. It was awesome to chat with you.

About this episode

Most B2B growth teams are doing more than ever.

More reps. More tools. More signals. More outbound. More dashboards.

And yet, for many teams, the pipeline still doesn’t follow.

That’s the tension at the center of this conversation with DeAnna Ransom, Chief Growth Officer at Betterbot.

DeAnna is rebuilding a GTM motion in real time from the inside. She’s not talking about this from the sidelines. She’s in the seat, doing the work, and seeing firsthand where the old growth math is breaking.

Her argument is clear: growth in 2026 is not a headcount problem. It’s a precision problem.

When teams add people to a motion that isn’t precise, they don’t fix the problem. They scale imprecision.

We get into why AI didn’t break outbound but held it up to a mirror, why teams often have data about people without actually knowing them, why visibility has to come before scale, and why retention is no longer just a customer success issue. It’s a growth strategy.

We also talk about the CMO tax, what it takes for marketing leaders to be seen as business leaders, and why the modern growth leader has to build a system precise enough to scale and human enough to trust.

If your team is doing more but getting less back, this conversation is worth sitting with.

About DeAnna Ransom

DeAnna Ransom is the Chief Growth Officer at Betterbot, an AI platform serving the multifamily industry.

She has more than 20 years of growth and leadership experience across B2B and nonprofit sectors. Her background spans sales, marketing, and customer experience, which gives her a different view of the revenue motion.

Instead of treating marketing, sales, and customer experience as separate functions, DeAnna looks at them as one growth system designed around the customer.

Chapters

00:00 Introduction: Growth Is a Precision Problem
01:13 More Activity Isn’t Creating More Pipeline
03:21 Data Isn’t the Same as Knowing the Buyer
04:48 Building a GTM Motion from the Ground Up
07:13 Using Retention to Sharpen Your ICP
09:26 Overcoming the CMO Tax
16:03 Why Retention Is Durable Growth
20:01 How to Start: Audit the Customers You Already Have
23:14 The Modern Growth Leader’s Role

A few things worth taking away

Growth teams don’t have an activity shortage. They have a precision problem.

Adding people to a motion that isn’t working can make the problem worse because it scales imprecision.

AI is not the core problem. It exposes whether your outbound motion is relevant or just louder.

Having data about a buyer is not the same as knowing the buyer.

Before you scale, you need visibility: attribution, forecasting, lead to cash, handoffs, leaks, stalls, and where relationships are weak.

Retention is not just a customer success metric. It’s one of the most capital-efficient growth levers a company has.

The best customers should teach you who to pursue next.

A quiet customer is not always a happy customer.

Marketing leaders need to come in as business leaders, not just campaign leaders.

The modern growth leader has to be both systems architect and translator.

A few lines that stuck with me

“When you add people to a motion that isn’t precise, it isn’t working. You’re scaling imprecision.” — DeAnna Ransom

“AI didn’t break outbound. It held it up to a mirror.” — DeAnna Ransom

“You can’t scale what you can’t see.” — DeAnna Ransom

“A quiet customer does not automatically equate a happy customer.” — DeAnna Ransom

“Your customers are your business.” — DeAnna Ransom

“The modern growth leader’s job is to build a system that is precise enough to scale, yet human enough to trust.” — DeAnna Ransom

Resources mentioned

Betterbot

DeAnna Ransom on LinkedIn

Transcript

Brian Carroll: Hello everyone, welcome to The B2B Roundtable. I’m Brian Carroll. Excited to be with all of you today.

What I keep hearing from leaders right now is this: they hired the SDR team, added the signals, added the technology, and their budget went up, but the pipeline doesn’t follow.

And so they hired more and they switched tools and they started a new initiative and the results still didn’t move. I’ve come to believe that this problem isn’t capacity, it’s precision. And most teams have more activity than ever, but they have less signal from real buyers.

My guest today said AI didn’t break outbound, it held it up to a mirror. And DeAnna Ransom is the Chief Growth Officer at Betterbot. She’s rebuilding the GTM motion in real time from the inside.

Now, if you’re a CMO, growth leader, or GTM operator who’s felt the squeeze between AI noise and being able to connect with your buyers, this conversation’s for you.

So, DeAnna, you said that growth in 2026 isn’t a headcount problem. It’s a precision problem. What are you seeing that makes you say that?

DeAnna Ransom: Yeah, thank you, Brian. First of all, thank you for having me today. Here’s what I’ve been seeing over the course of time. So there’s pre-pandemic, pandemic, and where we are today.

Over the course of time, what typically happened has been more reps, more spend, more activity. But that math in 2026 is completely broken. Capital has gotten super expensive.

Reaching people has gotten tremendously difficult. And when you add people to a motion that isn’t precise, it isn’t working, you’re scaling imprecision.

And so as you start hiring more and more people, people are a very expensive resource to bring in. And when you do that and you have not gotten precise, you have not done the fundamentals underneath it so that you can accurately target, understand, and connect, not just engage, connect.

The moment you see it and you’re adding these bodies, you’re going to stop because there’s no precision in it.

So I’m watching folks acquire more tools and do more outbound than ever before. They’re hiring more and more folks.

And you’re doing more, but what you’re actually getting back in the door is significantly less. I’m watching cold reply rates drop. They’ve dropped by almost half, I would say, in recent years. I think it’s gone from something like 6.8% in 2023 to something today around 3.4%.

So you have AI flooding inboxes, and you have outreach that is getting completely ignored. And it’s not ignored because the volume isn’t there or maybe the timing isn’t right. It’s because it’s not relevant. It is truly, truly noise.

And because of that, of course, if you are being ignored and you’re not relevant, you’re not going to get the result.

And that’s what I’m seeing. I am seeing the scale of noise versus the precision that creates relationship and relevance.

Brian Carroll: As I’m listening to you, I was just thinking about something you said: that teams have data about people without actually knowing them. So I wanted to hear from you, what’s the difference?

DeAnna Ransom: So the difference is when folks have a tendency to build an ICP. They start with an industry, they start with a title, and they go, great, this is what this person does, and they talk at that person.

Not with. They’re not starting a dialogue. They’re not understanding the human being.

People used to buy lists. Now you can do data append. People are using Clay. They’re enriching the data. You’re doing all the things to know about the person, but not knowing the person.

And I think that has become a major disconnect, especially in the rise of the pandemic when everyone went remote, one-to-one and real-life events went down.

So I really am seeing now that relationship building, really wanting to know the person, their pain, what they need, and understanding them on a human level before you even try to sell them, has just gone down.

We’ve got to fix that. There is the business piece, which is how we can use tools to connect, but it will never replace the human connection, which is the trust factor.

Brian Carroll: As you’re building this GTM motion in real time, and you’re building really from the studs up, what did you look at first?

DeAnna Ransom: Yeah, and I will be honest, before I think at all about a campaign or a hire, I look at what we can see. So the first thing that I wanted to fix was because you can’t fix what you can’t measure.

You can’t scale what you can’t see.

So what I did in very deliberate order was trying to get us to visibility first and a single source of truth. Attribution, forecasting, lead to cash. If leadership and the dashboard disagree, what are we doing?

I also wanted to dig in and do some ICP precision. Again, I’m not talking about what’s their title, what company do they work for from an industry, but who are our best-fit, highest-retaining customers?

Really from data and evidence and not from anecdote and aspiration. This is real work that, as an operator, you have to do before you start trying to send anything out the door.

And then the other thing is to look at where the motion itself leaks. Where does it stall? Where do the handoffs break off? Where are we single-threaded? Which means that it’s a weak relationship to begin with.

And for me, retention became where I focused a little more than acquisition. It was really plugging that back door.

Before we’re trying to go in and bring in more, because if you bring in more on the top of the funnel or in the front door, but you haven’t fixed and really understood and built a moat and a grounding and a relationship with your existing customers, all that’s going to happen is you’re going to churn out the backside.

And to me, that’s how you scale precision. That’s how you find who you really serve. And then you bring in AI as a layer, and then potentially only headcount if the system proves that it’s needed. That’s operational efficiency.

Brian Carroll: I really liked how you were talking about first focusing on visibility. And also I liked how you were focusing on who exactly is your ICP, not just total addressable market.

Not just focusing on acquisition. So much of marketing is spent on acquiring customers, but I like that you go beyond that and focus on the full funnel of retention and improving retention, potentially expansion.

So you’re using that as the template to understand who are your best customers and feeding that back into the system moving forward. Is that what I’m understanding correctly?

DeAnna Ransom: You are understanding that correctly, because then we know how to go and find more of those customers because we’re going to serve them well and they’re going to serve us well.

I believe that there has to be a mutually beneficial relationship to it.

And if you think about it, existing customers in this new dynamic, they are generating about 40% of your new ARR. That is a huge portion of your money.

And then if you think about what it costs to get a net new logo. Now, net new logos are celebrated. They’re the ones that get the confetti. But retention’s quiet. It’s also stable.

It’s also grounding.

And so I believe that when we expand, for me, I took over marketing, sales, and customer experience and created it as one motion, because that’s where you’re truly going to have growth.

So to me, my growth levers focus very strongly on how we are taking care of the customers we have, who are those best customers, and how can we continue to serve and expand within them.

And that is one type of growth lever. But then and only then are we looking at the net new, because that tells us who to go after and where to go to find them.

Brian Carroll: Really unique how you were able to tie all the pieces together from marketing, sales, customer success as part of your responsibility. How did you earn that credibility?

And maybe just as part of this, talk about quickly what Betterbot does. And then how do we overcome this tax as marketers, which is having to justify why do marketing in the first place?

No other function seems to have to do this. Finance doesn’t need to justify its existence. Sales doesn’t. I’d love to hear your perspective on this.

DeAnna Ransom: Yeah, I want to make sure I get all of the parts of what you asked.

So number one, over the course of my career I started off selling. Moved into marketing. I was in customer experience and led teams there. And so I probably have a very different perspective of how that works together as one unified revenue team motion.

I look at it that way because if you look at the dynamics of even the amount of time that a prospect spends with marketing now, it has shifted significantly.

At one point, they were spending about 60% of their time on the marketing side before they ever even wanted to speak with a sales rep. So as people were doing their own research and digging more deeply, marketing was owning more and more of a motion that they were always a part of, and that’s the sales motion.

And then you realize that there’s only one motion, and that is acquire and sell. It’s one motion with one team. So that’s kind of how I came to be in this as a leader and why I probably think about it as a unified, take-care-of-the-customer and create-this-virtuous-motion approach.

What does Betterbot do? Betterbot is an AI platform that serves in the multifamily industry. We literally power everything from the first touch of a resident’s journey all the way through to the retention side within the multifamily industry.

So again, we’re thinking end-to-end. Think of someone who is looking for their home and where they’re going to live, how they are taken care of as a resident, from booking the tour to signing the lease to living in the property, so maintenance and all those things, and all the way through to the other side, which is retention, or unfortunately, if they should move out.

If you’re with us, we’re hoping we’re getting some more retention. But we do that with an agentic AI platform. So we’re on the cutting edge of using agentic AI, and I have been able to take that and build that into our workflows for our revenue team.

And then you’re mentioning a little bit about how companies are taxing marketing.

Brian Carroll: How have you addressed it? Or, if you were coming into an organization as a new marketing leader, what might you do differently?

DeAnna Ransom: Well, when I come in as a marketing leader, I’ll start there, but I’m going to go back to the tax.

When I come in as a marketing leader, number one, I don’t come in looking only at my function. As an executive leader, in order for us to work together cohesively and solve the real business challenges and truly move a business forward, it’s not just about a function.

At that point, we are looking at it as a business leader, understanding the fundamentals of the business, the unit economics, the marketplace.

I don’t come in and look at campaigns and tactics and branding strategy. I can do that and it will get to that at some point. And I can have teams that can run that. But I come in as a business leader.

And it’s important that as marketers we come in remembering what our contribution to the business is, not just the function of marketing.

We come in behind the eight ball when we allow ourselves to be pigeonholed into a functional element. And so it becomes very important to have honest conversations about what the business really wants to achieve overall and to not speak in terms of just the function.

The function becomes how you can serve the business, but it is your business expertise and understanding of it that will allow you to craft the marketing elements.

That is hugely important. That is a distinguishing factor that I think we have to come in as marketing leaders with, understanding beyond a promotion or a campaign.

I want to sit down and understand what’s our three-, five-, ten-year plan. I want to talk about what are the levers we want to pull to truly drive growth in the business. Are we considering not just new verticals, but are we also looking at partnership economics? Are we thinking about ways that we can use our technologies to serve other industries? Do we have a force-for-good multiplier?

There are things that we can really start to do from a business perspective.

The tax piece is a challenge that’s been around for an extremely long time. When I was Chief Marketing Officer at Televerde, we talked about this constantly.

And there is not another function of the business that tends to have to prove itself again and again and again. And many times we talk with folks who everyone tends to think they’re a marketer. I feel like I found my tribe, so I’m hoping this is resonating.

Brian Carroll: Right.

DeAnna Ransom: A campaign is not marketing. It is a marketing tactic.

And so it is incumbent on us, whether we like it or not, to step back and go, hey, if you’re looking for someone that’s just going to run campaigns, that’s probably more of a marketing manager function that you can hire for.

I’m here to serve the greater good of the business and to look at how we are going to interlock and evolve the business overall and be able to drive growth.

And that’s a business conversation. That’s a P&L conversation. It’s very different than a marketing budget conversation. So we have to up-level that.

Brian Carroll: I like it. What you’re saying is we cannot be pigeonholed into thinking marketing is a demand generation function. If that’s all you think of as marketing, then you’re getting pigeonholed, because when you’re a strategic marketing leader, you’re looking at the long term of the business, as you talked about, the five-, ten-year plan.

Looking at the growth, looking at how the business is going to evolve, looking at new markets. And these all require a long-term point of view.

I wanted to ask you: you’ve been writing about this back door of retention, and I think it’s really a different point of view because so much emphasis is put on acquisition. And you’re talking about retention, expansion of your customer base.

So why do you think growth teams overfocus on new logos when durable growth often lives with the customers you’ve already won?

DeAnna Ransom: I can answer it very simply, which is it isn’t sexy. I believe I said it before, but new logos are visible. And they’re celebrated.

Retention is super quiet. Teams pour resources at the front door, building SDR teams, outbound motions, and the revenue is leaking out of the back door. The math has flipped.

In 2026, the most durable and capital-efficient growth lives with the customers that you have already won. And retention is the same discipline as good acquisition. It’s a continuation of getting to know the customer continuously and not just billing them.

Net revenue retention is the defining metric for me for 2026. A business at 120% NRR grows a $10 million base to $25 million in five years just on expansion. Let’s just sit with that.

Brian Carroll: So NRR, this is net revenue retention. Am I understanding that correctly?

DeAnna Ransom: You are correct. And it’s an important metric because if you’re thinking about budgets going down, you need to do things in the most operationally efficient way possible.

And we know that you talked about folks wanting a dollar for a dollar. That’s not how the math works in net new. It just does not. It’s about two dollars or more for a net new logo acquisition.

When you’re thinking about expansion, you are roughly at that dollar for dollar. So why would you not, when you’re thinking business and true efficient growth and not on a functional tactic, why would you not focus on your back door and take the best care of your customers and continue to grow and expand with them?

Brian Carroll: What you’re saying is, if we increase our net revenue retention, you’re reducing your customer acquisition cost because it is more spend a dollar, get a dollar versus whatever the ratio is, a two-to-one CAC or whatever that turns out to be. What you’re saying is, it just makes economic sense.

DeAnna Ransom: Yes. It is like I keep saying it, I’m going to hammer that. It’s capital efficient.

You don’t have to go and start from the beginning. You have them as a customer. And so you’re having your cost there. Your cost of sale actually goes down tremendously because you’re just expanding within them.

You’re continuing a conversation and you’re not using the same resource.

I’m going to say this again because if you’re looking at it from a P&L perspective, when you are having your customer experience team and they understand from an account management perspective how to care for the customer and continue to expand within the customer, that’s a different line than having a costly sales executive going out and hunting and bringing in a net new customer.

So you’re actually multiplying the savings in who’s taking care of that customer and being able to expand within it. It’s twofold.

Brian Carroll: Well, I’m thinking about it from the point of view of a listener today who maybe hasn’t explored looking at net revenue retention, looking at this as a growth driver. What would you suggest to someone to get started to explore this? What would be that next best step?

DeAnna Ransom: One of the things that I did as a first step, just to make sure before we could even get to any type of ICP, was an audit of our customers.

And I’m not talking about just who are our customers, what are the logos, but I dug in a little deeper to understand who they are, segmenting them, how many of them are reporting tickets versus how many of them are excited, how many of them have participated in our NPS and what scores they have given us.

Really wanting to understand how we’ve been serving them, what feedback have they been giving us, what are the things that they’ve been coming with.

I highly recommend starting with an audit of your customers so that you really understand who they are, which ones are at risk.

Because a quiet customer does not automatically equate to a happy customer.

You need to understand, we’re talking signals, Brian. You need to dig in and understand what are the signals. What are the trend lines of, hey, I’ve had about three customers get quiet and then six months later they dropped. You might want to pay attention to that.

Dig in and understand who you already have. How do I care for them? Who’s at risk? Who’s truly happy? How do I amplify the happy? Expand within the happy? Understand the unit economics.

Are these good customers in the sense that they are profitable? And here’s what I mean by that. Some customers, are you continuing to have to pour so many resources into it that they’re actually not a profitable customer?

How many folks are taking the time to really understand the business and the shape of the business from that perspective? That can tell you a lot about where to go forward.

So I highly suggest that deeper audit and understanding of your existing customer base so that you can, A, work with at-risk customers, B, work through the expansion economics of being able to grow without more capital, and then C, know where to point your outbound resources.

Brian Carroll: This is something I know a lot of marketing teams aren’t doing enough, which is going in and really investigating who our customers are.

For whatever reason, after the sale happens, that’s the responsibility of customer success, or that’s the responsibility of sales, or that’s the responsibility of the account manager. But what I love you’re saying is, no, start by understanding your customer first.

Is there anything else you’d add to that?

DeAnna Ransom: Well, the only piece I’d add is that you want to understand it because your customers are your business. As a business leader, they are your business.

And so understanding them will then help you to understand more about your business, where it’s weak, where it’s performing well, so you know where to pour gas and what to fix.

Brian Carroll: I’d love to talk about what the modern CMO or chief revenue officer or growth leader needs to become now, especially as AI is changing our work and buyer behavior is changing as well.

What do you think a CMO or revenue leader needs to become today to meet these challenges?

DeAnna Ransom: Yeah. I think about it all the time. If you go back to the tax that we are hit with that we’ve been chatting about, and the systems and where we are in the marketplace, the modern growth leader’s job to me is to build a system that is precise enough to scale, yet human enough to trust.

I think that is where we have to come from.

It’s two things at once. It’s a systems architect and a translator.

The architect piece, because marketing, sales, and customer experience, I don’t believe, this is my personal perspective, I don’t think that we can any longer operate as these three separate functions. We have to have shared metrics. We have to operate as one growth system that’s really designed around the buyer.

The translator piece for today’s marketing leader is because now you have to be fluent in AI operations, in revenue operations. I mentioned unit economics, but you still have to be the most empathetic person in the room.

You still have to be the one that is championing and advocating for the customers and the business.

And so I think in this world, in this moment, the title matters a little bit less than the scope. Owning the whole motion as one system and wanting to own it from a business perspective is what I think today’s modern leader is going to need to do.

Brian Carroll: Do we know these people or do we just have their data?

And I think that’s the question every growth team needs to be asking or sitting with right now.

It’s going to put you in place for something that actually works.

And you’ve heard DeAnna Ransom today. She is the Chief Growth Officer at Betterbot. And you can find DeAnna on LinkedIn. I recommend you follow her.

And if you found this episode helpful, you can subscribe. We’ll also be providing the links and resources and transcript in the show notes.

DeAnna, once again, thanks for joining us.

DeAnna Ransom: Thank you so much for having me.

Most B2B marketing still runs on a single number: the marketing qualified lead. Jon Miller is one of the few people who can tell you where that number came from, because he helped build the system that produced it — first at Marketo, where he helped create the marketing automation category, then at Engagio, then at Demandbase.

What makes this conversation different is that Jon went back and diagnosed his own creation. He’s not quietly onto the next thing. He’s saying, out loud, what the MQL got wrong about how people actually buy — and he’s careful to credit what it got right before he takes it apart.

The short version: roughly 95% of buyers have built their shortlist before they ever talk to a seller. The MQL was designed to catch the last 5% who raise their hand. So the real question isn’t how to optimize lead capture. It’s what you do with everyone who isn’t ready yet — the 95% the old model was built to ignore.

We get into why buying behaves more like weather than a vending machine, the three-tier model Jon uses instead of MQLs, why he thinks legacy automation tools can’t keep up, and how the best CMOs are quietly rewiring what they report to the board. If you’ve ever felt like you were pedaling into a headwind running the playbook that used to work, this one’s for you.

About Jon Miller

Jon Miller founded Marketo in 2006 and helped define the marketing automation category. He went on to found Engagio, which was acquired by Demandbase in 2020, served as CMO at Demandbase, and is now building Phave, an AI-native marketing automation platform.

Chapters

00:00 Introduction to Jon Miller and his journey
01:24 Diagnosing the MQL model
03:27 The gumball machine / nonlinear buying idea
07:23 What the MQL got right
10:14 The three-tiered model of engagement
14:22 The role of CMOs in modern marketing
18:17 AI’s impact on marketing automation
19:55 The Spotify playlist analogy
22:53 The Peppers and Rogers/one-to-one thread
24:43 Common mistakes moving off the MQL
25:25 The three CMO dashboards
27:25 Advice for CMOs making the shift

A few things worth taking away

• The MQL started as a good idea — a contract between marketing and sales — and got gamed over time as teams chased volume.
• Buying isn’t linear. With six to sixteen people on a buying committee researching in places you can’t even track, “run a campaign, get a lead” no longer describes reality.
• Hand raisers are the gold standard, but waiting for them means you only ever talk to the 5% who already built their shortlist without you.
• Jon’s three tiers — hand raisers, MQX, and MEX — give you a way to work the 95% instead of ignoring them.
• When you move off MQL volume as your headline metric, expect the numbers to drop before quality and conversion rise. Set that expectation early, or you’ll hit a buzzsaw.
• The strongest CMOs report pipeline across all sources to the board and stop fighting over who sourced what.

A few lines that stuck with me

“Put your quarter in, get your gumball out. Put your campaign in, get your MQL out. I just don’t think that’s the way buying works.” — Jon Miller

“If you only wait for somebody to raise their hand, you’re talking to the 5% in market. And they’ve already built their shortlist without you.” — Jon Miller

“You can’t get there with a rules-based system. You just end up with spaghetti.” — Jon Miller

Resources mentioned

• The B2B CMO Project — research on the strategic CMO and the three-dashboard model
• Mike Bosworth, Solution Selling
• Don Peppers and Martha Rogers, The One to One Future
• Kathleen Schaub, Marketing in the Great Big Messy Real World

Transcript

Brian Carroll (00:05) Welcome to The B2B Roundtable, where we go inside the ideas, people, and decisions shaping modern revenue teams and how they actually work. I’m Brian Carroll, and today my guest is Jon Miller.

I first met Jon way back in 2006, when he founded Marketo and helped build the marketing automation category as we know it today. In 2015 he founded Engagio, which was acquired by Demandbase in 2020. Now he’s building Phave, an AI-native marketing automation platform.

Here’s what makes this conversation different from other podcasts you’ve listened to: Jon didn’t just build the next thing and quietly move on, the way a lot of founders do. He’s gone back and started diagnosing the problems with something he previously created. He’s talking about what’s wrong, and why it’s failing buyers today.

And here’s why it matters right now. Before they ever talk to a seller, 95% of buyers have already designed their shortlist. The MQL is built to capture the last 5% who self-identify. What about the 95% who haven’t yet?

So, Jon — when did you first start thinking the MQL model was broken, not just underperforming? How did you get there?

Jon Miller (01:24) It started, more than anything else, during my time at Demandbase. After we merged Engagio and Demandbase together in 2020, the first thing I did was help the product team unify the two platforms. But then in 2021, I took over as CMO.

And I had my playbook. This is how I do it: I create definitive guides, big, rich, meaty pieces of content. You run lots of other thought leadership, like webinars, and you generate leads from all of it. Most of those leads won’t be ready to buy right now, and that’s okay — that’s why you nurture them and score them. You know a little something about that. Then eventually, when they’re ready, you pass them to sales. That was the playbook, and it’s the playbook I ran at Marketo.

To a degree, it’s the playbook I ran at Engagio too, although there we also layered on an account-based motion that we’ll get to. So here I am at Demandbase, running that playbook, and the exact same tactics that worked for me at Marketo just weren’t working.

At Marketo, it felt like I’d had a tailwind pushing me forward, making everything work better. At Demandbase, it felt like bicycling into a headwind. That’s what got me thinking: okay, what’s going on here? Over time, I diagnosed multiple problems — like most complex things in the world, there were many reasons it wasn’t working.

Jon Miller (02:56) But more than anything else, it came down to three things. One, buyer saturation. Two, the fact that the traditional model missed important things like brand. And three, the fact that the MQL is really focused on people, not accounts. We can dive into any or all three of those.

Brian Carroll (03:15) I want to understand what you noticed was broken first. As you’ve reflected on it and done the research — what are we getting wrong about how buyers buy today?

Jon Miller (03:27) Let’s start with the core philosophy behind the MQL: that you can run a campaign and get a meaningful response that’s valuable on the other side. That’s how we thought of it at Marketo. If I needed more MQLs, the natural response was, well, let’s run more campaigns.

It trained us to think of buying like a gumball machine. Put your quarter in, get your gumball out. Put your campaign in, get your MQL out. And I just don’t think that’s the way buying works. Arguably, in the early days of Marketo — simpler buying committees, heavy demand, lots of latent need for our product — okay, maybe you could argue there were elements where it worked then.

But fast forward to today, and buying is much more complex. There are six to sixteen members of the buying committee, not one person. And as you said in the intro, that whole committee is going through a complex set of research — happening not just on our website, but increasingly off it, in closed communities and in conversations with AI agents, all invisible to traditional tracking.

When you have that kind of complexity, the model of marketing as a simple linear gumball machine starts to break down. Kathleen Schaub coined a really good term for this, which connected to my math and physics background. She called it “marketing in the great big messy world,” and she pointed out that marketing is actually a complex, nonlinear process — not a simple linear gumball machine.

Jon Miller (05:19) I studied complex nonlinear processes in college, and it turns out that’s the origin of what’s now called chaos theory. The weather is a complex nonlinear process. The stock market is a complex nonlinear process. And these processes are known, among other things, for their unpredictability — their sensitive dependence on initial conditions. The idea that a butterfly flapping its wings in Brazil can cause a hurricane in Japan. Most people have heard that one.

If you embrace the fundamental idea that buying is just as complex as the weather, then it’s an impossible task to say, “I’ll run this one campaign, and that will lead to buying.”

Brian Carroll (05:46) That’s right.

Jon Miller (06:03) Or, “Where did this deal come from?” “Well, they stopped by the booth at the trade show.” No — it’s a much more complex system than any of those simple explanations can really capture.

Brian Carroll (06:16) The gumball machine analogy hits on something people are really struggling with. Attribution. The MQL has been elevated all the way to the board — board members and CEOs care about it because it’s a visible KPI. And there are a lot of misses in how we think about it, because we don’t actually know how many MQLs become real customers. Partly because of what you just described about how buyers buy.

You wrote something on LinkedIn about a three-tier model — this marketing-engaged layer, where people are consuming content but not showing buying signals yet. Most demand gen teams would say those aren’t worth chasing, because there’s no buying intent yet. Can you make the case for why that’s wrong? Why is that exactly where the fight is being lost?

Jon Miller (07:23) It’s worth starting by saying there was some real goodness in the original concept of the MQL. Specifically, it was a contract between marketing and sales. Marketing said, “I’m only going to pass you things that reach this bar, where there’s strong evidence this is worthy of sales attention.” And sales said, “Okay, I commit to this service-level agreement for follow-up.” That was a genuinely good thing about the MQL.

The problem is that over time it got bastardized. Under pressure to hit pipeline targets, some marketing teams gamed the scoring thresholds. I saw so many companies basically say any responder to any campaign was an MQL. And I’d think, that’s not what it was.

That behavior — driven by the desire for more MQLs — is exactly what led sales to start cherry-picking and ignoring most of them. So what was sales cherry-picking? Hand raisers.

Jon Miller (08:31) I’ve talked to some CMOs who say that’s the only thing they report now: hand raisers. People explicitly asking for a sales connection. And that makes sense — these are people you want to talk to. But I think it’s a hundred percent too passive.

Jon Miller (08:49) And it’s too late. If you only wait for someone to raise their hand, you are by definition only talking to the 5% in market. Those people have already created and aligned on their shortlist without you, which means you’re column B, fighting an uphill battle at best.

Mike Bosworth wrote Solution Selling a while ago, and there’s a lot of wisdom in that old book. The idea of solution selling is that helping a buyer see pain they haven’t prioritized — bringing latent pain into an active evaluation — is really valuable. And if you can be the vendor guiding that process, you help shape the buying criteria. So the question is: how do we make that happen?

One way is an investment in branding. Building a brand that creates urgency around the problem you solve, builds a connection between your company and the ability to solve that pain, and generates positive feelings around that connection — that’s incredibly valuable. We could do a whole other podcast on branding.

But there’s the question of how you tie solution selling together with the goodness the MQL brought to the table. Because solution selling gone wrong just becomes cold calling, and that’s not good for anybody.

That’s why I came up with the three-tier model. The top tier is hand raisers. Let’s all agree that’s the gold standard — it’s what sales wants more than anything, and we should track it. But then there are two other tiers. Tier two I call MQX.

The X is important, because making the X stand for “lead” usually isn’t the right answer — unless you have a low-value, highly transactional purchase that one person can make. Most of the time, it’s a more complex buying committee. So I’d generally say tier two should be MQA — marketing qualified account — or even MQBG, marketing qualified buying group. As a sidebar, MQBG is a mouthful, so I usually drop the M and just call it a QBG.

What these all have in common is some signal that there’s a good chance this account or buying group is actually in an evaluation stage — starting to form their shortlist or consensus, maybe they already have. You’re not waiting for them to raise their hand. If you can reach out to those companies at the right time…

Jon Miller (11:46) …in the right way, it can be valuable. The key is that MQX does not mean this person is ready to buy. It means marketing believes, based on the data, that this account might be in market. There’s an interesting debate about whether we should even call it “qualified,” because it’s not qualified the way a salesperson uses that word.

I like using it because it’s a familiar mental model, but you could also call it a marketing recommended account or a marketing indicated account. If the word “qualified” carries baggage at your company, fine — use something else. Then there’s my third tier.

Jon Miller (12:27) I call it MEX — marketing engaged account. This is really the 95% that aren’t in market. You could cold call into that 95%, but the idea of MEX, as opposed to just your target account list, is that it’s someone from your target list who’s also engaging with your brand and ideas. There’s some level of engagement, even if there are no buying signals. They’re showing interest in your topic, even if not intent to purchase. Odds are that’s a warmer outreach than a truly cold call.

But 100%, do not reach out to that person and pitch a demo or a sales meeting. This is about what Bosworth calls solution selling — helping them understand and quantify the cost of the status quo, and creating hope about what the future could be, maybe by sharing examples of what other companies are doing.

That’s not how typical SDRs reach out today. It’s a one-to-one way of building brand and awareness. And a person with “sales” in their title might not be the right person to do it — which is why some companies have MDRs, market development reps. But that means different economics and different compensation. You can’t pay an MDR on this quarter’s pipeline if what they’re doing is planting seeds for a year from now.

Brian Carroll (14:13) That’s right.

Jon Miller (14:13) So that was a lot of framework. But I think hand raisers, MQX, and MEX make a lot of sense.

Brian Carroll (14:15) A lot was going through my head listening to that. You brought up brand, you talked about engaging differently, and you touched on how SDRs work. The current playbook has an SDR follow up on a scored lead, incentivized one way: get a demo, schedule an appointment. So they’re focused on the last mile, the end of the buying process — but the majority of leads they talk to are nowhere close to that. They’re in the early stages.

You’ve been digging into this through CMO dinners and conversations. How are CMOs responding right now? What are you seeing and hearing, and what do you think teams need to do to get from where they are to where they need to go?

Jon Miller (15:21) I see a wide variance in how marketing leaders are responding to these pressures. This is a dramatic oversimplification, but you can bucket most marketing leaders into either a strategic CMO or a tactical CMO.

The tactical CMOs, whether they want to be or not, work at companies that primarily view marketing as pipeline generation. They’re pressured into the traditional playbook and traditional metrics — MQLs, marketing-sourced or marketing-influenced pipeline. These CMOs will give the right kind of acknowledgment — “I know the MQLs aren’t right, and I’m reporting on these other things too” — but they still feel like, “Yeah, but I have to report the MQLs.”

The strategic CMOs are the ones elevating the role. First and foremost, they’re executives of the company who bring their understanding of the market and the customer, so they’re in the room when strategic discussions happen. It’s the concept of the CMO as chief market officer, not chief marketing officer. Those CMOs are driving conversations about the changing buyer, the importance of brand, and the need to think long-term, not just short-term.

Jon Miller (16:54) That said, they’d all agree that pipeline is permission. Even a strategic CMO, if they’re consistently missing pipeline, doesn’t get to go invest in the big new brand project. They get that. But how they tackle it, and how they talk about it, feels a little different. That’s probably the biggest delta — and it runs through into the dashboards they present, how they interact with their peers, and how often they talk to the CFO and about what.

Brian Carroll (17:29) It sounds like the tactical CMOs are more subject to that gumball-machine dynamic — MQLs, driving demand, generating the numbers. And for the strategic CMO, it’s not that they ignore those things; demand generation still matters. But they’re thinking bigger picture about strategy, like how important brand is in B2B.

I want to pivot to one of the challenges all of us are dealing with right now — not just brand, but the technical environment we’re operating in. I’d like to talk about how AI is changing what’s possible. Whether you’re a strategic or tactical CMO, it has a huge influence. What can you do differently for these marketing-engaged leads, for example? How might we approach that?

Jon Miller (18:35) Part of the problem is that tools like Marketo — which I obviously helped create — were built around the mental model of the MQL, of marketing as a linear, simple buying process. In rules-based platforms, very much if-this-then-that, you end up with static nurture paths. You’re lucky if you have two or three paths for two or three personas, let alone understanding the right thing for each person in each account.

When you embrace the modern buying process, where 95% aren’t ready to buy, you need to create latent pain, stay in touch with that 95%, and then catch the signals when they might be becoming qualified — pre-hand-raiser, but ready to reach out. The legacy tools like Marketo just can’t keep up with that. The nurture tracks are too rigid and too limited for engaging the broad market before they’re ready to buy. And they’re too email-centric for when you don’t have permission for a huge fraction of that database.

The analogy I like is that instead of putting people in specific nurture tracks, we want to create a personalized playlist for each person. I like playlists because people understand Spotify. There’s a whole library of songs that could play at any time. But…

Brian Carroll (20:19) That’s right.

Jon Miller (20:20) …what their AI does is think about me — what I’ve liked and listened to, what I’ve engaged with, what I haven’t listened to in a while — and it builds a playlist for me. Even if you and I both like 80s songs, we’ll get different playlists, because we’re different people who’ve engaged with different things. Every single person on Spotify gets a completely unique, personalized playlist.

Can we use AI to apply that same idea to marketing? For the 95% that aren’t in market but that I need to engage over time, let’s craft a personalized playlist for each of them — based on who they are, where they work, what else is happening across their buying committee, and what we know about them.

If we have opt-in permission, that playlist should include email touches — but it won’t always. Sometimes it’ll involve advertising. It might involve LinkedIn touches. It could be a whole variety of ways to interact, by picking the right offer, the right channel, the right content, and the right time.

So legacy marketing automation is rule-based and list-based. It’s too person-based, meaning you can’t really build playlists that look at the account level and go multichannel into advertising.

Jon Miller (22:01) One other thing, which we haven’t talked about: our whole conversation so far has focused on net-new business — acquiring the new customer, the new account. But a lot of these concepts — hand raiser, MQX, MEX — also apply to post-sale, especially for expansion into new buying committees, product qualified leads or accounts, and product adoption campaigns. The legacy tools don’t handle any of that well either, and new AI-enabled approaches can. Which, not surprisingly, gives you a pretty big hint at what I’m trying to build at Phave.

Brian Carroll (22:28) So Phave — that’s what you’re working on right now. AI-enabled marketing automation to deliver these personalized, one-to-one journeys. It sounds like the promise is kind of like what I was reading way back in Peppers and Rogers’ one-to-one marketing, except now we can actually do it — the way you described with the playlist. Anything you’d add?

Jon Miller (22:54) It’s funny you bring up Peppers and Rogers. In the intro, you said I’m an entrepreneur who keeps coming back and revisiting what I’ve done before. The way I describe my journey — from Epiphany, the company before Marketo, where I wasn’t a founder, to Marketo to Engagio and now Phave — I’ve been on a journey to deliver on the one-to-one future.

Each of those companies would have said we’re trying to do one-to-one marketing. Each got us closer, but not quite. What I’m so excited about, living in 2026 in the age of AI, is that I think we’ll finally be able to deliver on what truly is one-to-one marketing, as envisioned by Peppers and Rogers back in 1992.

Brian Carroll (23:47) That vision has been around a long time, but with every iteration we’ve struggled to get there. There was always some limitation. And it seems like right now, the promise of AI to actually deliver on it is real.

Jon Miller (24:02) You can’t get there with a rules-based system. You just end up with spaghetti.

Brian Carroll (24:05) Yeah. Anyone who’s built very complex nurturing journeys knows there’s an eventual breakdown. The more personalized you want to get, there are only so many if-then statements and branches you can build before it gets too complicated — and it still doesn’t do what you’re trying to do.

For listeners thinking, “Okay, what does this mean for me right now?” — how can someone move their organization away from MQL logic? And what are the most common mistakes you’ve seen teams make when they try?

Jon Miller (24:43) The common mistakes. First, doing it alone, without full alignment and buy-in from the rest of the executive team. The single best thing a CMO can do is enlist the head of sales — and the head of post-sale, if they exist — and propose the new set of metrics as a team. That’s number one.

Number two, when you start changing these things, set the expectation that quantity is likely to go down. The quality will go up and the conversion rate will go up. But if people don’t expect the raw numbers to be lower, you can run into a buzzsaw and get into trouble.

What I recommend is that CMOs be very thoughtful about their measurement architecture. We actually published a research report about the strategic CMO on the B2B CMO Project website, where we talked about three types of CMO dashboards.

The first is what you show the board. At the board level, these should be business outcomes. First off, the best strategic CMOs own pipeline — they report on pipeline created, new and expansion, across all sources. That last piece is the key. You’re not reporting marketing-sourced or sales-sourced; you’re reporting on whether there’s enough pipeline for the business. Because at the end of the day, if there is, the board doesn’t care who sourced it. And if you believe in complex nonlinear buying, trying to track where a deal came from is a fool’s errand.

From there, marketing can share in reporting other key metrics — opportunity win rates, net revenue retention, customer acquisition cost. The last board-level one is marketing efficiency: total pipeline generated per dollar of marketing investment. That’s your top level.

Your second level is CEO- and CFO-level indicators. This is where things like hand raisers and MQAs kick in, along with pipeline quality and brand health. Then you save everything else for the marketing team’s operational metrics — including MEX, that third tier: market development metrics, account engagement, program performance. That’s all important, but it doesn’t belong in your CEO- or board-level reports.

Brian Carroll (27:25) If you could go back and have someone give you advice on what to do differently — what advice would you give a CMO who’s ready to make this shift?

Jon Miller (27:36) Some of what I already said — building a committee, working with your peers — is really important. But if I had to narrow it down to one thing, it’s this: earn your seat by being a business executive first.

Surface problems, in marketing and in the market, before other people do. That builds credibility. Spend a lot of time with your peers — the CRO, the CFO. Understand their challenges. Then you’re in a better position to demonstrate how marketing helps them, not just marketing.

And own the customer voice. I alluded to this earlier, but it’s the single most powerful thing the chief market officer can bring to these strategic discussions. If you’re a strategic CMO who’s established that level of credibility, people aren’t going to question the metrics you report — whether it’s MQLs, MQAs, or anything else — because they know you’re a strategic part of the leadership.

Brian Carroll (28:42) Excellent advice, Jon. We’ve covered what I hoped we would today. This matters so much, because as the buying dynamics have changed, people need to approach things differently. What you’ve shared is going to help a lot of people start thinking about how to address the 95% who aren’t in market.

We’ll share the resource Jon mentioned in the show notes. Jon, thank you for joining us today. I’m excited to see how things develop as you build Phave, and I’m really glad you could be on the show.

Jon Miller (29:15) Thank you. It’s been a pleasure.

Most B2B buyers say they would rather buy without talking to a sales rep.

That sounds like a sales problem. Brent Adamson says it is deeper than that. Buyers are not just avoiding sellers. They are struggling to make confident decisions.

Brent is one of the clearest voices in modern B2B sales. He is co-author of The Challenger Sale, the book that changed how many sales and marketing teams think about commercial conversations. In this episode, we talk about his new book, The Framemaking Sale, and why the next era of sales depends less on persuasion and more on helping buyers make sense of complexity.

The short version: buyers do not need more information. They already have too much. They need help knowing what matters, what to ignore, who to involve, what questions to ask, and how to move forward with confidence.

We get into why 75% of B2B buyers prefer a rep-free buying experience, why customer confidence matters more than supplier confidence, how framemaking differs from Challenger, why thought leadership can make buying harder, and what AI changes about the role of the human seller.

If your sales or marketing team is still trying to prove value by adding more content, more insight, or more follow-up, this conversation will make you rethink the job.

About Brent Adamson

Brent Adamson is a researcher, speaker, and author best known for co-authoring The Challenger Sale and The Challenger Customer. He spent years leading research at CEB, later Gartner, on B2B buying, sales effectiveness, and commercial transformation.

His latest book, The Framemaking Sale, focuses on how sales professionals can help buyers make confident decisions in a world of complexity, information overload, misalignment, and uncertainty.

Connect with Brent on LinkedIn

Get the book: The Framemaking Sale

Chapters

00:00 Why buyers prefer rep-free buying
04:12 Becoming the seller buyers want
09:40 What buyers need from salespeople
11:35 Why decision confidence matters
16:05 What framemaking means
21:26 Framemaking and The Challenger Sale
25:39 Buyers need sensemaking
28:18 Helping teams become framemakers
35:01 Marketing’s role in framemaking
39:34 AI and the future of human selling

A few things worth taking away

• B2B buyers are not always trying to avoid humans. They are trying to avoid sales interactions that make buying harder.
• The 75% rep-free statistic measures buyer preference, not buyer reality. Many buyers still have to talk to sellers, but that does not mean they want to.
• Decision confidence is one of the strongest drivers of high-quality, low-regret deals.
• The confidence that matters most is not the buyer’s confidence in your company. It is the buyer’s confidence in themselves and their own decision.
• Most sales and marketing teams are still trying to build supplier confidence. Framemaking shifts the goal toward customer self-confidence.
• Buyers are overwhelmed by complexity, information overload, internal misalignment, and uncertainty about outcomes.
• The Challenger Sale helped sellers reframe the customer’s thinking. The Framemaking Sale helps customers make sense of competing ideas so they can decide.
• Thought leadership created a new problem. Everyone sounds smart, so buyers are left with more content, more claims, and less clarity.
• Marketing can support framemaking by interviewing customers about the buying journey, not just the product outcome.
• The best question from Brent: “If you had to do it all over again, what might you do differently just to make your lives a little bit easier?”
• AI may answer questions, summarize options, and produce tables. But buyers may still want to talk to someone they trust before making a hard decision.

A few lines that stuck with me

“The data does not say 75% of B2B buyers would prefer a human-free experience.” — Brent Adamson

“What would it take to be the one seller, the one sales team, that your customers actually do want to talk to?” — Brent Adamson

“It’s not customers’ confidence in us that matters. It’s customers’ confidence in themselves.” — Brent Adamson

“While we’re all in sales and marketing solving for getting customers to know something, the single biggest secret passage to growth is getting customers to feel something.” — Brent Adamson

“What if your value as a seller isn’t your expertise, but your access to the experience of other companies like them?” — Brent Adamson

Resources mentioned

• The Framemaking Sale by Brent Adamson
• The Challenger Sale by Matthew Dixon and Brent Adamson
• The Challenger Customer by Brent Adamson, Matthew Dixon, Pat Spenner, and Nick Toman
• Gartner research on rep-free buying experiences
• Robert Cialdini, Influence, and the idea of social proof
• CEB / Gartner research on decision confidence
• Ecosystems and value management maturity models

Listen and subscribe

If you found this episode helpful, subscribe to the B2B Roundtable Podcast wherever you listen.

Full transcript

Brian Carroll:
Welcome to the B2B Roundtable Podcast, where we bring together ideas, people, and strategies shaping the future of sales and marketing.

Today, I’m joined by my friend Brent Adamson, one of the most influential voices in sales. You may know Brent from his book The Challenger Sale, which reshaped how we think about commercial conversations.

I’m excited because we’re talking about his new book, The Framemaking Sale. And it couldn’t come at a more urgent time. In a recent survey, 75% of B2B buyers said they’d prefer to purchase without ever talking to a sales rep. Is this the end of sales as we know it, or could it be the start of something better?

We’re going to talk about why buyers have lost confidence in sales, what’s driving this shift, what it really means to be a framemaker, how leaders like CMOs and VPs of Sales can build teams customers actually want to talk to, and what the future of selling looks like in an AI-driven world. Brent, you open your book with that stat — 75% of B2B buyers would prefer a rep-free buying experience. That’s wild.

Brent Adamson:
First of all, it’s great to see you, Brian. Thanks for the invite. That statistic comes from Gartner research, one of the last pieces I worked on before leaving in 2022. We asked thousands of B2B buyers: “If you could buy a large complex solution without ever talking to a sales rep, would you prefer that?” Seventy-five percent said yes.

Now, that doesn’t mean they actually buy without sellers. It means they’d prefer not to. The data shows a big and growing gap between customer preference and customer reality. That gap represents risk for sellers.

Brian Carroll:
So it’s not the end of sales. It’s the end of salespeople not adding value.

Brent Adamson:
Exactly. The question at the heart of this book is simple: What would it take to be the one seller — or the one team — that customers actually do want to talk to? If you can be that person, showing up less like a seller and more like a human, you can differentiate not only from competitors but also from the overwhelming flood of information customers already face.

Buyers don’t want more information. They want confidence.

Brian Carroll:
What are the ways sellers unintentionally undermine buyer confidence?

Brent Adamson:
One of the biggest findings is around decision confidence. When customers feel highly confident in their decisions, they are up to 10 times more likely to make a high-quality, low-regret purchase.

But most sales and marketing teams focus on building confidence in the supplier — “trust us, our brand, our product.” What actually matters more is the buyer’s confidence in themselves.

The real opportunity is helping customers feel confident in the questions they’re asking, the research they’ve done, their alignment as a team, and their ability to execute. That’s what framemaking is all about.

Brian Carroll:
Can you define framemaking? How is it different from Challenger Selling?

Brent Adamson:
Framemaking is about creating the context — or frame — that helps customers make sense of complexity and move forward with confidence.

It’s built around two key moves: prompting and bounding.

• Prompting means introducing ideas or perspectives they may not have considered.
• Bounding means narrowing focus so they can prioritize what matters most.

Together, those moves create a frame that gives customers both ease and agency. The decision feels simpler, and they feel like they made it.

Challenger is part of this lineage. It’s about teaching and reframing. But in today’s world of overwhelming content, simply adding more insights isn’t enough. Customers don’t need another smart idea. They need help making sense of all the smart ideas already on the table.

Four forces undermining buyer confidence

Brent Adamson:
In the book, we unpack four big challenges that undermine buyer confidence:

1. Decision complexity — too many people, too many steps.
2. Information overload — endless content, conflicting advice, and AI adding even more noise.
3. Objective misalignment — different stakeholders with competing priorities.
4. Outcome uncertainty — even if they believe the solution works, buyers fear their team won’t implement it well.

The job of a framemaker is to help buyers navigate these challenges by simplifying, prioritizing, and guiding them without taking away their sense of ownership.

From Challenger to Framemaker

Brian Carroll:
If I’m a VP of Sales or Marketing, how do I coach my team differently? How do I stop undermining confidence?

Brent Adamson:
Challenger was about showing up with powerful insights. That still matters, but in today’s content-saturated world, simply adding more insights can overwhelm customers further.

What buyers need now isn’t just more ideas. They need help making sense of all the ideas. That’s where framemaking comes in. It’s not about proving how smart you are. It’s about helping customers feel smart and confident in themselves.

Brian Carroll:
That word, sensemaking, is powerful. Buyers are overwhelmed. They don’t want another rep adding noise. They want someone to help them make sense of it all.

Brent Adamson:
Exactly. And that’s the opportunity. Show up as the one person who helps buyers cut through complexity and feel good about moving forward. That’s how you become the rep they actually want to talk to.

A story of framemaking in action

Brent Adamson:
One of my favorite examples is from a sales rep we call “Tara.” She sold human capital management solutions. In a discovery meeting with the head of HR, she suggested bringing procurement into the conversation early.

Most reps would avoid procurement until late in the process. But Tara said: “In working with other customers like you, we’ve found that when procurement gets involved earlier, things go much smoother. You might consider inviting them now.”

That simple nudge reframed the process, avoided future roadblocks, and built customer confidence. That’s framemaking in action. It doesn’t have to be grand. Sometimes it’s just a well-placed phrase that frames the decision differently.

Marketing’s role in framemaking

Brian Carroll:
What role does marketing play in this shift?

Brent Adamson:
A huge one. Marketing can gather stories, lessons, and pitfalls from customers and feed them back into sales plays and content. Instead of just creating thought leadership about the supplier, marketing can create confidence content: tools, checklists, benchmarks, and diagnostics that help buyers feel more confident in themselves.

Imagine win-loss analysis focused not on why customers chose you, but on what they wish they’d done differently in their buying journey. That insight is gold. It can shape sales plays, create useful collateral, and make your content strategy far more valuable.

AI and the future of selling

Brian Carroll:
With AI moving so fast, what does the future of sales look like?

Brent Adamson:
AI can surface options, compare vendors, and even create frameworks. But at the end of the day, customers are still human. After all the data, many will say, “I just wish I could talk to someone.”

The sellers who thrive will be the ones who become that someone. The person who helps customers feel clarity, confidence, and connection. That’s the future of sales.

Closing thoughts

Brian Carroll:
Brent, you landed it. At the core, this is about empathy and human connection.

Brent Adamson:
Yes. There’s never been a better connection between doing what’s right for sales and doing what’s right for humanity. If you want to hit quota, win big deals, and earn that President’s Club trophy, the way to do it is by helping customers feel confident in themselves.

Brian Carroll:
And that’s what The Framemaking Sale is all about. If you want to dive deeper, get a copy. It’s packed with strategies, stories, and tactics that will change the way you sell.

Brent, thanks as always for joining me.

Brent Adamson:
I appreciate you, man.

Most teams don’t struggle because they lack automation or content. They struggle because they’re guessing about the buyer’s journey instead of understanding it.

At best, nurturing becomes educated guessing.
At worst, it becomes scaled annoyance.

And in a world where AI and automation can multiply messages instantly, bad nurturing doesn’t just waste time. It erodes trust faster than ever.

Buyers don’t experience funnels.
They experience relevance, timing, and intent.

When those are missing, even “helpful” messages feel intrusive.

This is why lead nurturing fails when teams guess the buyer journey.

The Real Problem Nurture Is Supposed to Solve

Most leads are not uninterested.

They’re unresolved.

They stall because priorities shift, internal consensus breaks, risk feels too high, or timing simply isn’t right yet.

Traditional funnels assume steady, forward motion. Real buying journeys don’t work that way.

Buyers pause. They loop back. New stakeholders enter. Urgency fades and returns.

Nurture exists to manage uncertainty over time.

Not to push.
Not to remind.
Not to “stay top of mind.”

Its role is to preserve context, build trust, and support progress when buyers are actually ready to move.

(Related reading: Why Lead Generation Was the Wrong Mental Model)

Progression vs. Activity

One of the most damaging assumptions in marketing is that more activity equals more progress.

It doesn’t.

Open rates are activity.
Clicks are activity.
Form fills are activity.

Progress looks different.

Progress shows up as:

• Clearer problem definition
• Better internal alignment
• Reduced perceived risk
• Increased confidence to engage

Buyers don’t move because you sent more emails. They move because something became clearer or safer.

Nurture should answer the buyer’s next question, not repeat your last message.

Nurture as a GTM System Function

When nurture works, it doesn’t live in one place.

It shows up across inbound follow-up, outbound sequences, SDR conversations, sales follow-ups, closed-lost re-engagement, and account expansion.

That’s why treating nurture as “marketing’s job” breaks the system.

Nurture is a shared GTM system function.

It connects:

• Demand Clarity – who this system is for
• Lead Management – how signals flow
• Sales Development – how humans engage
• Executive decisions – what the system optimizes for

When these parts are disconnected, nurture becomes guesswork. When they’re aligned, nurture creates continuity across the buying experience.

Why Lead Nurturing Fails Without Lead Management

This is the part many teams miss.

Lead nurturing isn’t primarily a content problem. It’s a lead management problem.

When your lead management system captures the right signals, nurturing becomes helpful instead of spammy.

Those signals include:

• Fit against your ideal customer profile
• Intent vs. casual interest
• Buying-group engagement
• Where the buyer is actually stuck

When those signals are missing, nurturing turns into noise dressed up as personalization.

Effective nurture depends on a system that makes the journey visible, then routes the next best action with context.

This is the bridge between GTM systems and real pipeline movement.

(See: How to Do Lead Management That Improves Conversion)

Where Lead Nurturing Breaks Down

Most nurture programs fail in predictable ways:

• Teams guess buyer stage based on content consumption instead of buyer reality
• Automation replaces judgment and scales weak assumptions
• Context is lost at handoffs, quietly eroding trust
• Email becomes the system instead of one tool within it

These are not tooling problems.

They are system design failures.

The Real Risk of “AI-Powered” Nurturing

AI doesn’t make nurturing smarter by default.

It makes it faster.

If your assumptions are wrong, AI will help you be wrong more efficiently.

The teams winning with AI aren’t sending more messages. They’re using better signals and stopping messages sooner when relevance drops.

Automation should amplify understanding, not replace it.

The Bottom Line

Lead nurturing isn’t about moving leads through stages.

It’s about helping buyers move through uncertainty.

That only happens when nurturing is grounded in real customer understanding, supported by strong lead management systems, and designed to build trust instead of pressure.

If your nurturing feels busy but ineffective, don’t add content or automation.

Fix the system. Learn the buyer. Then scale.

Where to Go Next

• Who is this system actually for?
  Start with Demand Clarity and Ideal Customer Profiles.
• When is a buyer truly ready for sales?
  That’s the role of a Universal Lead Definition.
• How do signals move without losing context?
  Explore Lead Management and Flow.
• What does this look like in practice?
  See the case studies.

Customers care more than ever about the values of the companies they buy from.

It is more than purpose. It is more than what you sell.

They want to know what kind of company you are, what you care about, and whether your company exists to do more than drive profits.

That is why I interviewed Dr. Philip Kotler, known as the father of modern marketing. Dr. Kotler is the S.C. Johnson & Son Distinguished Professor of International Marketing at the Kellogg School of Management at Northwestern University and co-author of Brand Activism: From Purpose to Action.

In this conversation, Dr. Kotler explains what brand activism is, why trust in institutions has fallen, how customer expectations have changed, and why companies need to think carefully about purpose, reputation, and action.

We also talk about what brand activism means for B2B companies, why it cannot be treated as a marketing campaign, and how leaders can use frameworks, scorecards, and customer research to make sure their actions are authentic rather than superficial.

About Dr. Philip Kotler

Dr. Philip Kotler is widely known as the father of modern marketing. He is the S.C. Johnson & Son Distinguished Professor of International Marketing at the Kellogg School of Management at Northwestern University.

He is the author and co-author of many influential marketing books, including Brand Activism: From Purpose to Action.

Chapters

00:00 What is brand activism?
02:21 Why brand activism matters now
04:05 The evolution of branding
06:53 How customer expectations changed
09:01 Brand activism in B2B
14:24 Why this is not just marketing
16:59 What marketers can do
20:47 A framework for brand activism
24:49 Authenticity, empathy, and action
28:41 Where to learn more

What is brand activism?

Dr. Kotler: Brand activism is a movement toward making a brand do more than just tout the virtues of a product or a service, its usual function, and to identify some value or values that the company has and cares about.

For example, The Body Shop, when it started under Anita Roddick, was not only selling skincare products. The company was also fighting for animal rights, civil rights, fair trade, and environmental protection.

So, her brand was active. I do not mean that all other brands are passive, because they do a lot of work. But the implication is that companies carry reputations, and they want to carry a good reputation.

More and more consumers would like to know what kind of company this is and what it cares about.

Our society is saddled with many problems. Does the company care about any of these problems, or does it just think it is supposed to make money?

An increasing number of companies would like an identity that goes beyond just making the product or service. That is what we are calling brand activism: the brand that connects with some cause or causes.

A lack of trust in society

Brian: That is a helpful distinction. You recently wrote a book on this topic. I would love to know the story behind why you wrote Brand Activism and why now.

Dr. Kotler: If you look at barometers, like the Edelman Trust Barometer, the level of trust in society today has certainly been falling.

As a result, many companies are not going to be trusted either, as part of government not being trusted and other institutions not being trusted.

Companies ought to be the first to fight against bad companies, rather than stand near them or be part of them.

At this time, companies want to be profiled in a certain way. The reputation a company has could be whatever happens in its course of behavior. Or it could be something designed better.

Consciously better.

What are the stages of branding?

Dr. Kotler: The whole idea of a brand has gone through several stages. I think brand activism is probably the highest stage.

Brian: That would be great.

Dr. Kotler: The first stage is when the company simply does its best to feature the good side of its product and services. The brand name was an identifier.

Then brands moved into trying to define the company’s positioning, but not social positioning. Just their positioning: Walmart is lowest price, Disney is family entertainment, DuPont is highest quality, and Toyota is long-lasting, reliable performance.

In that second stage, the brand became not just one mentioning a product, but positioning the product.

Then the brand moved further to define a set of qualities about the company. For example, John Deere might describe itself by its quality, integrity, and innovation.

This is really positioning, but it is multi-positioning. It says the company stands high on a number of traits that most people value.

But this could move into a fourth stage where the brand adopts a very specific cause. A company may say it cares about the climate problem and wants to help move solutions toward keeping a safe climate in the world. Or it could be some other cause.

Then brand activism is alive with that development: going from corporate social responsibility to the company saying, “Here is one of the things we are going to move forward on, to the extent that we can afford to do it. We want to make more useful products, make money doing that, but we also want to push forward some cause that would help all of us.”

So that is the evolution of branding, and brand activism is one of its latest stages.

How have customer expectations changed?

Brian: What has really been driving brand activism, and how have customers changed their expectations?

Dr. Kotler: Customers were asked how they feel about the economy and society. We would hear them talk about concerns and fears related to immigration, a decline in ethics, gun control, high federal budgets, high debt, and education failure.

There are all these social issues, and they become the ground out of which brand activism becomes important.

We would say that companies do not have the right to be silent about these issues.

An increasing number of people would argue that companies owe it to their consumers to show that they care for more than just their product and making money.

That is the groundwork that inspired brand activism.

What about B2B companies?

Brian: Do you see a difference between B2B companies and B2C companies with brand activism?

Dr. Kotler: No, I do not see a difference. I think both types of companies will want their reputation to go beyond just making their product as well as possible.

If you take equipment companies like John Deere or consumer companies like McDonald’s or Coca-Cola, many B2B and B2C companies have made their brands more active.

Brian: Some of the brands that come to mind are Nike, Patagonia, Ben & Jerry’s, and Starbucks. Do you have B2B examples people could look to? I was thinking perhaps Salesforce.com or Apple.

Dr. Kotler: I am glad you mentioned Salesforce.com because Marc Benioff is one of the pioneers in this area.

He has been distraught about homelessness and affordable housing in San Francisco. He personally encouraged other companies in San Francisco to pool their money in a fund that could be used to double the budget for fighting homelessness in San Francisco. That kind of thing comes from a B2B company.

I would think that B2B companies have generally been slower as marketers. Most of what we know about modern marketing, aside from sales training and thinking, came from the consumer side.

It is not just a sales thing

Dr. Kotler: It was P&G and Unilever that created a difference between the concept of sales and the concept of marketing.

A company might say, “I do marketing because I have a salesforce and I advertise.”

That is not marketing.

That is just having two resources that could be used within the marketing framework. It is not equivalent to creating a sound and effective total strategy that will keep a firm alive and well for years to come.

Marketing is more than just sales.

That concept of marketing came to the B2B world later than it came to the B2C world. But then B2B discovered marketing and is doing more with it now. I think they will do more with brand activism.

Remember, B2B companies are very close to their customers. Consumer companies do not know as much about individual customers. B2B companies know through the salesforce every buyer and what they are like.

Pretty much any business buying from another business knows a lot about the values of the seller. That is why they are buying from that seller.

There is less need for B2B companies to get into brand activism because it is happening anyway.

Brand activism is not just marketing

Brian: Brand activism is not a marketing thing, right? It goes deeper into business strategy and purpose. Do I understand that?

Dr. Kotler: Absolutely. No CMO will take the brand that he or she is responsible for protecting and enhancing and suddenly move into brand activism alone.

That is a corporate-level decision. No one plays around with choosing an issue like gun control, the environment, or overcrowded prisons and just does it through the marketing department.

This is part of designing and protecting the firm’s reputation and meaning.

We often see the word “purpose” coming up now in the literature.

What is your purpose as a company?

“Well, I make cars.”

That is fine. But fundamentally, what are you contributing? How are you justifying your company in terms of making life better in society?

Brand activism works best when inspired by leaders

Dr. Kotler: Brand activism must come down from the top. It should be discussed at several levels of the company.

One benefit of being brand active is that your employees may be more turned on to the company and its contributions.

They tend to be proud of their company because it cares about more than just making widgets.

That is probably a motivation for the CEO and the executive suite to choose values carefully and put them into the brand framework.

It can help not only current customers, but also attract more customers and excite employees about the company’s purpose.

What can marketers do?

Brian: I get that marketers cannot do this on their own. It needs to come from the CEO, the board, and the executive team. So what can marketers do to support brand activism?

Dr. Kotler: If the impulse is going to come from the CMO, here is what can be done.

Let us say you are in a company that is not doing brand activism. There is no display of its values or the issues it cares about.

One could ask, “Wouldn’t it help if we start worrying about the future of water and whether there will be enough to make our Coca-Cola?”

The water problem will be a very big issue in the future. Maybe the marketing group should bring that to the executive suite and put into the brand work some mention of conserving and protecting good water.

So it is possible that senior management is stimulated initially by someone in marketing who sees that it would be a good move to refresh the brand.

The CMO’s role in the process

Dr. Kotler: Every brand gets tired over time.

One of the key requirements of the CMO is to be able to kick that old view of the brand and put in some fresh insight and meaning.

The brand manager who begins to care a lot does not have to be quiet about it and may successfully get the company at the top level to endorse the issue.

The CMO can research any issues that might arise or embarrass the company by taking that cause.

If there is any level of real risk, brand activism probably will not be adopted.

I believe brand activism is something to be brought to the attention of senior management by the CMO, or in another way, to consider taking action.

A framework for brand activism

Brian: As I understand it, you put together a framework so people can put brand activism into their organization. Can you describe that framework?

Dr. Kotler: The first need was to describe the different types of brand activism chosen by a company.

The first type is social activism. That means taking a stand on gender, LGBT, race problems, aging problems, education, or healthcare.

The second is workplace activism. The company might address issues of corporate organization, CEO pay, worker compensation, or labor and union relations.

The third is political activism, such as lobbying, voter rights, or gerrymandering.

The fourth is environmental activism, with concern about air and water pollution, emissions, and conservation.

The fifth is economic activism, where the company takes a stand on wage and tax policies that affect income inequality and the redistribution of wealth.

Finally, there is legal activism, where the company discusses policies that impact corporations, such as tax policies, citizenship policies, or employment laws.

That is the framework. We provide maps, canvases, and scoring systems that can help a company get serious about adopting brand activism.

A scoring system helps a company understand how it was viewed before it went into brand activism, what it expected to accomplish in the minds of customers and the public, and how impactful the adoption of that issue has been.

It can also help measure the effect on sales growth, profit levels, market share, and other outcomes.

We need a scoring system to know if we should increase brand activism on that issue, stay where we are, or decide it is not working at all.

Being authentic and genuine

Brian: The thing I am hearing is that we need to decide our purpose or reason for being beyond money. From there, the framework helps show where we are today and how we can improve.

How do you see empathy fitting into this for the customer? Sometimes companies “pink it up” for women’s issues, but it is not authentic. Do you have thoughts on that?

Dr. Kotler: We are concerned about authenticity. Promoting an issue can get lost in superficial talk by the company when there is no real commitment.

We would say to the company: “You are active about being against pollution. What have you done with that position?”

If the only thing you have done is talk against pollution, but take no action, then we are not impressed.

There is a term you may remember, green-grassing. It is about appearing to be a green company through talk, but not doing much about it.

I believe there should be research with customers. For example, ask whether customers know if Company X cares about some social issue.

If, after doing brand activism, hardly any customer noticed that you took a stand on that issue, then it is not working. Probably because you are just talking it up and not committing.

When it works well, brand activism enhances the value of the firm in the minds of existing customers, employees, and potential customers.

It may even be an entry point. Discussing pollution, for example, can open your company to people who do not know much about your company but care deeply about pollution. They may be happy to see another ally in that fight.

The word empathy suggests this question: Will customers feel that the company is sincere and genuinely cares about the issue, or will they not believe it is authentic?

Additional resources

The Case for Brand Activism — A discussion with Philip Kotler and Christian Sarkar

Purpose matters to marketing

Get the book: Brand Activism: From Purpose to Action

Why does so much marketing stink?

Michael Brenner has a direct answer: “Most of the marketing that we do that stinks and doesn’t work is because some executive with a big ego asked us to do it.”

That line gets to the heart of this conversation.

Bad marketing usually starts inside the company. It starts when teams make decisions around internal pressure, executive preference, sales requests, product priorities, or ego instead of asking what actually helps the customer.

In this episode of the B2B Roundtable Podcast, I talk with Michael Brenner, Former CEO of Marketing Insider Group and author of Mean People Suck, about why empathy matters in marketing, leadership, and business.

Michael argues that empathy is not soft. It is one of the most practical ways to improve marketing, build stronger cultures, help employees feel more engaged, and create better customer experiences.

We get into why marketers feel frustrated, why many companies still create marketing customers do not care about, how to put the customer back at the center of the business, and why the simple question “What’s in it for the customer?” can change the work.

If your team is tired of creating marketing that checks internal boxes but fails to help buyers, this conversation is worth your time.

About Michael Brenner

Michael Brenner is the Former CEO of Marketing Insider Group. After a 25-year career inside corporate marketing departments, Michael built his work around content marketing, employee activation, thought leadership, and helping companies create marketing that serves customers.

He is the author of Mean People Suck and The Content Formula.

Connect with Michael:

• Mean People Suck
• @BrennerMichael on X/Twitter

Chapters

00:00 Introduction to Michael Brenner
01:20 Why Michael wrote Mean People Suck
03:35 Why so many marketers feel miserable
05:15 Why empathy matters in marketing
09:20 Why customers do not care about brands
13:30 Why the buying journey does not start with your product
16:00 Putting the customer at the center
23:00 Asking “what’s in it for the customer?”

A few things worth taking away

• Most bad marketing is created to satisfy internal requests, not customer needs.
• Marketers struggle to care for customers when they do not feel cared for inside their own companies.
• Empathy is tied to employee engagement, customer loyalty, retention, and business performance.
• Customers do not care about your brand as much as your company thinks they do.
• The buying journey usually starts with the customer’s question, not your product name.
• Marketing should help customers solve problems, not just promote the company.
• A better org chart would put the customer at the center, with every department asking how to serve them.
• The best marketing and selling feels like helping because it is helping.
• The question “What’s in it for the customer?” can stop a lot of wasted marketing activity.
• The three pushback questions are simple: Who is this for? Why is it important? How are we going to measure the impact?

A few lines that stuck with me

“Most of the marketing that we do that stinks, that doesn’t work, is because some executive with a big ego asked us to do it.” — Michael Brenner

“The math isn’t enough to get people over the challenges that we’re facing and how to do marketing that doesn’t suck.” — Michael Brenner

“The companies that have effective marketing are those that are empathetic.” — Michael Brenner

“We just aren’t that important. We’re not as interesting or important as we think we are.” — Michael Brenner

“The buying journey doesn’t start with a search for our product.” — Michael Brenner

“We wouldn’t do half of what we do if we asked what’s in it for the customer.” — Michael Brenner

Resources mentioned

• Mean People Suck by Michael Brenner
• The Content Formula by Michael Brenner
• Marketing Insider Group
• 2019 Marketer Happiness Report from MarketingProfs
• The Service Profit Chain from Harvard Business Review
• Mean People Suck Companion Guide PDF

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Full transcript

Brian Carroll:
Michael, welcome to our show. I’m so excited to have you here with us today. Can you tell our listeners just a little bit about yourself?

Michael Brenner:
Yeah, sure. Thanks for having me, Brian. It’s great to talk to you today. As you know, I’m Michael Brenner. I’m the CEO of Marketing Insider Group. After a 25-year career inside corporate marketing departments, I went out on my own and started squarely in the B2B marketing and content marketing space, now branched out into content development, employee activation, and thought leadership programs. I’m fortunate enough to get to run around the world sometimes and give speeches. It’s been a blast, and I feel really fortunate to be able to do what I do.

Brian Carroll:
So cool. For our listeners, you may not know this, Michael, but you’re one of the very first people I interviewed when I first launched this podcast. That was like three years ago.

Michael Brenner:
Yeah, exactly.

Brian Carroll:
It was funny because we were talking about this topic of empathy, and I just would love for our audience, can you tell us this story? You just wrote a new book, and that’s what we’re going to talk about today. For those who are watching the video, can you hold it up? What’s the book title? Mean People Suck. Tell me why you wrote the book. Why now?

Michael Brenner:
Again, I have to give you credit. You were out in front of this empathy topic in marketing I think long before me. Kudos to you. It just took me a little bit longer, but essentially as a content marketer and as a former internal corporate marketer, I reached out to folks that I know that are still living and breathing corporate marketing struggles every day.

One of the things I found was that they were miserable. It’s almost like that scene from, I think it’s Poltergeist, where the obsessed woman has “help” written on her. Was it Poltergeist? No, I forget which horror movie it was. Maybe it was The Shining. I can’t remember.

Anyway, there was a woman possessed and the words “help” showed up on her stomach because I feel like a lot of internal corporate marketers feel that way. They’re miserable.

When you get down to it, what I’ve found is that it’s largely because they hate their boss. They don’t love the corporate culture. They’re not happy with what they’re being asked to do. They feel they don’t have an impact.

When I looked at why content marketing programs aren’t successful, the answer superficially was content ROI. What’s the ROI of content? And if you don’t mind me, I’m not being promotional, but I actually wrote a book called The Content Formula, all about content marketing ROI.

And when I went back to folks I sent the book to, what I found was that it wasn’t enough. The math isn’t enough to get people over the challenges that we’re facing and how to do marketing that doesn’t suck.

The reason I wrote the book is that most of the marketing that we do that stinks, that doesn’t work, is because some executive with a big ego asked us to do it.

Brian Carroll:
Right.

Michael Brenner:
Executives love seeing logos on stadiums, and they love seeing Super Bowl ads, and all the things that we make fun of marketing about largely come from a request from sales or marketing or product people.

The companies where content marketing is successful or marketers are happy are making an impact because there’s a culture of empathy. Their cultures don’t suck. The companies don’t suck. The leaders don’t suck. That’s why I wrote the book. Maybe a long-winded explanation, but that’s why.

Brian Carroll:
Well, and I think you’re also just talking about the state of affairs for marketers. It’s hard for marketers to actually care about the customer when they themselves aren’t necessarily cared for. They don’t feel safe. They’re anxious, or they’re frustrated, or they’re challenged.

You also talked about empathy. It seemed like this book was written for two people: for those who are experiencing this, but also for leaders. Why does empathy matter especially to marketers, and does it lead to better results?

Michael Brenner:
Yeah. One of the stories that I tell in the book, the very first corporate book that I read, and I have to give credit to the former CEO at Nielsen, my first company who made most of us in the company read the book. And I was like, “Oh, here we go.” And I read the book. I was like, “Wow, this is actually really pretty cool.” It’s called The Service Profit Chain. I write a lot about it.

It’s a book that isn’t talked about much, but the premise is simple. Three or four Harvard Business Review professors got together and said, wait a second, we’ve seen this correlation between engaged employees, happy employees, happy customers, and higher stock prices, happier stock investors.

Brian Carroll:
Right.

Michael Brenner:
They did some actual research and found that where there’s employee engagement, there is customer loyalty. Where there’s customer loyalty, there’s higher spend rates and retention and higher stock prices.

The key to those environments, those cultures, those companies where there were happy employees was empathy. The company’s purpose was to make their employees happy because they knew happy employees created happy customers.

It’s totally intuitive and yet it’s counterintuitive. That’s one of the reasons we reconnected was my LinkedIn post, “Empathy is the counterintuitive secret to success.”

The thing is, I think life has beaten us down and gotten us to believe that we should take what we want and put our elbows out and get to the front of the line. It’s actually the opposite. It’s counterintuitive that if we help people, we can actually get what we want.

It’s definitely true for marketing, which really has a bad reputation. Most people think marketing is propaganda and promotion, but the companies that have effective marketing are those that are empathetic. It’s those that are empathetic to their customers and don’t just create promotion and propaganda.

Empathy really is the key in marketing and business and in life. I wrote the book trying to straddle all three of those perspectives. I hope your listeners out there take a look, and hopefully they can get back to me and tell me how well I did to try to straddle those three.

Brian Carroll:
Well, I just want to say I’m excited for you. I’m excited for this book because big-picture empathy, or caring for customers, or wanting to help people, is pretty easy to talk about. Right? I think if you were asking your own executives, do you care about your customers? Do you have empathy for your employees? I don’t think anyone would argue with that, but it’s easier to talk about than it is to do.

One of the things you talked about was the customer journey and what the experience is for customers, why they don’t care about brands anymore, and how brand doesn’t matter. So why is that?

Michael Brenner:
Well, the first thing is I think it’s important for marketers and especially brand marketers, corporate marketers, but also I think those who are in the trenches need to understand how to explain this to executives. And that is that we just aren’t that important. We’re not as interesting or important as we think we are.

My former company, Nielsen, did a survey of brands and found that 77% of consumers said they wouldn’t care if the brands they use disappeared completely. We’re seen as replaceable in many aspects.

While we think we’re super important and we think we’re super interesting in the companies we work in, our customers are just trying to get through every day and trying to meet the challenges they face. They’re trying to stay awake. The bar is low.

Yet so many brands don’t create any kind of messaging or stories that resonate. And so that’s really the trick: if you truly care about your customers, you don’t talk about yourself as much.

When I meet somebody new, I don’t say, “Hi, my name is Michael Brenner, and I’m awesome.” That’s the last thing I would ever say. If I want somebody to actually listen to me, I say, “Hi, how are you?” My first thing is outreach. It’s empathy. It’s not promotion and propaganda and ego.

I think we just forget that sometimes when we’re sitting inside the corporate marketing department.

Brian Carroll:
Well, you’re illustrating the point that empathy is easier to talk about than it is to do. Part of what I’m hearing you say is we’ve got to overcome our own bias thinking that we have the answer.

Really often I think marketers come from the perspective, “If I were the customer, how would this appeal to me?” Or as you talked about the leader who wants to see the logo, well, that’s not a customer-focused decision in their calculus.

How might marketers use empathy in their approach to customers? What are some of your thoughts on that from your work and research?

Michael Brenner:
In my first book, The Content Formula, I talk about my year-long struggle to get my colleagues inside SAP to see and to have empathy for our customers. I started with data. The data often leads to the conclusion that, for example, at SAP we were selling a cloud computing solution called SAP HANA, which now has a little bit of brand awareness but then didn’t have any.

What I tried to show my colleagues in marketing was that people weren’t searching for our product name. They weren’t searching even for SAP cloud computing solutions. They were searching for things like “what is cloud computing?”

In every industry, no matter what thing you sell, if you sell cybersecurity solutions and you sell the world’s greatest cybersecurity solution named Alpha, I’m just making this up, people aren’t searching for Alpha as much as they’re searching for cybersecurity solutions.

When I found the data didn’t work, I moved to fear, FOMO in a way, but really fear. I went to the sales team and actually showed them that I use this term, “the buying journey doesn’t start with a search for our product.” And the sales team understood that actually better than my peers in marketing.

I used search. I said, “Hey look, when I type cloud computing into Google, IBM and Oracle and Salesforce show up, but SAP didn’t show up at all.” They got angry. That anger then translated to direct mandates over to my peers in marketing, who finally created the atmosphere and environment for me to create customer-focused content.

It was kind of like a mafia move, if you will. I kind of strong-armed them to see that it was the right thing to do.

Brian Carroll:
It’s interesting though because I think, here’s the thing. You and I talked about this offline before. When marketers are in our buildings, who is talking to customers more, marketers or salespeople?

Michael Brenner:
Yeah.

Brian Carroll:
I think the point you made is you went to the people who were talking to the customer.

Michael Brenner:
Yeah, exactly.

Brian Carroll:
They had that insight. And ironically, we’re in marketing. We’re supposed to influence messages of customers, but we actually are not in the building.

I want to ask you a question. You have a lot of great stories in your book. Do you have a favorite story? And if so, which one?

Michael Brenner:
Yeah. One of the things I talk about in how to create empathy inside the organization is to rethink the org chart. I talk about how org charts are boxes and lines, and they show who’s above and below us. Basically, they show who directs orders down to the minions who do the work.

I talk about how org charts miss the most important person, and that’s the customer. I’m not suggesting every company should recreate the org chart, but if we rethink the org chart, it would look more like a bullseye.

You have the customer at the center, and all the departments branching out from there would be thinking, how should I best serve this customer? There are a couple of stories in the book of people, and they’re not all necessarily marketers, but certainly a few who’ve done that.

One is Amanda Todorovich from Cleveland Clinic. She has a very famous empathy video. If you Google Cleveland Clinic empathy video, you’ll see an internal video. It was originally created to help executives inside Cleveland Clinic see that Cleveland Clinic is more than just a business. It’s more than a hospital operation.

It’s an organization that serves patients. The concerns that patients have are matters of life and death and giving birth and dying. Amanda’s team’s video was extremely impactful. I get chills just talking about it. I use it in every presentation, and it has 4 million views online.

They released it publicly at the request of their executive team because they really understood the impact of, hey, what makes us different isn’t because we have great surgeons and we have utilized some certain technique or equipment. What makes us unique is that we really care for our patients.

It’s empathy tied to a corporate mission, all the way down to the content that Amanda and her team create every day, which serves patient needs. That’s one of my favorite stories from an empathy perspective.

There are probably 15 stories. I could keep going. I’ll stop myself because I love talking about the people I call champions, the champion leaders, the people that celebrated others and achieved success because of that.

That’s the counterintuitive nature of empathy. It’s help others, live your life in service of others, and you actually get what you want. That’s really at the heart of the book.

Brian Carroll:
Well, in my experience, I 100% agree. Personally, for our listeners, at some point in time, my Jerry Maguire moment was by actually not focusing on convincing people.

I’ve always had the best marketing and selling feels like helping because it is. The reality is I realized my Jerry Maguire moment is I wasn’t living that. I was trying to convert people instead of connect and help.

The irony is, when you actually focus on, “Hey, what do they care about? How can I help them?” What I love with Cleveland Clinic is it’s not just a marketing thing. It’s what they do.

In my own experience, by not trying to get leads, I got 303% more just by helping people. It’s crazy.

Do you have tips for developing deeper empathy that you could share with our listeners? I know you wrote a book that has exercises that go deeper, but anything someone listening can come away with to begin saying, okay, I don’t disagree, but how?

Michael Brenner:
Yeah. There are a couple of tools I wanted to develop for your listeners. For the people who were like me, sitting and getting asked to do stuff that we know won’t work, the highest-level insight is ask what’s in it for the customer.

For example, your sales leader comes over and says, “I’d like a brochure for this niche industry event we’re going to.” It’s going to cost you $4,000, and it’s a couple of designers and a printer to get created. Just ask, “What’s in it for the customer?”

Do people really read our brochures? Are they going to throw it right in the trash? You might think it’s important to stuff that inside the conference bag, but I’ve never read a brochure myself from a conference.

If we ask what’s in it for the customer, as opposed to thinking of our jobs as just doing what the sales team or the product team or our boss tells us to do, the answer I think is sometimes surprising. We wouldn’t do half of what we do if we asked what’s in it for the customer. And so that’s the highest-level tip.

I offer three deeper level questions. I call it the pushback. It just goes a little bit deeper.

• Who is this for?
• Why is it important?
• How are we going to measure the impact?

If you ask those three, those are three deeper-level questions from the “what’s in it for the customer?” overview.

Again, you wouldn’t put your logo on a stadium. You wouldn’t create a brochure that costs a lot of money to print and kills trees. You wouldn’t do a lot of the things that we do that we roll our eyes about when we think about marketing and all the propaganda that comes outside of companies.

Brian Carroll:
It’s so funny as I listen to you. As I talk with marketers, often VPs will lament, and we forget what it’s like to be a customer even though we’re all customers ourselves. That’s kind of the crazy thing.

Some of the things that we think suck, are we doing those same things when we reach out to our customers? We’re the recipients of marketing. We’re the recipients of sales messages.

Any other thoughts? Because I wanted to highlight you just because your message is so important. It’s so timely, and it’s so needed. But any other things you wish I would’ve asked about before we close?

Michael Brenner:
No, I think we’ve covered the main tips. I appreciate you bringing me on and letting me share these tips with the readers. I’d love for your audience to read the book.

Again, everything I do, I’ve done in support of this desire to try to help people. I started blogging before I had a business just because I wanted to share what I know. The keynotes I give, the books that I write, and even the client work that I do get paid for is really to try to help people, and it’s worked for me.

I don’t think I’m smarter than other people. If it works for me, I think it’s the secret for many of us to live a life that’s maybe a little more meaningful, a little more impactful.

I just talk to so many people. I talk about this crisis of engagement and empathy. The world feels like a meaner place these days.

The three takeaways from the book are: be kind, be cool, be you.

Be kind is just because it’s the right thing to do.

Be cool is don’t take things personally. A lot of the mean people we meet aren’t psychopaths and narcissists. They’re just having a bad day.

Be you is because the people who are living their fullest life know what their purpose is, and they’re working in support of that. It’s often in service of others. So that’s how I’ll leave it.

Brian Carroll:
Well, and as I listen to you, I’ve always felt and believed marketing can and should be a force for good. Often people view it as being about manipulating and coercing. It’s like, no, it’s actually about making a difference, helping people achieve results, and helping people transform in positive ways.

What’s the best way to connect with you and find out more about your book?

Michael Brenner:
Well, you can check it out at meanpeoplesuck.com. You can find more about me at marketinginsidergroup.com. I’d love to connect with your folks personally on LinkedIn, Facebook, or Twitter at BrennerMichael.

Brian Carroll:
And for our listeners, Michael has offered to share some resources. You’ll find them in the show notes. I’ll provide those links along with the story. I’ve made some notes of things that we’ll share as well. Really excited for you. Thank you again for being with us today, Michael.

Michael Brenner:
Yeah, thanks again, Brian.