So you’ve got a startup idea swirling around in your head. As an initial step, you might grab a coffee with a trusted friend and ask, “So what do you think?” and poke around for some early research into the competitive landscape. But as “The Mom Test” has taught us, this sort of casual idea validation with friends and family is not nearly enough to build an enduring business that can go the difference — more rigorous customer discovery is required. 

Yet all too often, founders and product leaders fail to make this leap. Some neglect the research process entirely in the early days, instead waiting until they’ve spun up an MVP for folks to test out. Others do start talking to potential customers when the idea is still squishy and moldable, but without processes and structure in place to ensure this is time well spent.

Jeanette Mellinger, Head of UX Research at BetterUp and former Head of UX Research for Uber Eats, has spent her career helping folks do this right. She also spent years as First Round's User Research Expert in Residence, teaming up with early-stage startup leaders as they formulate and validate their ideas.

“When I started working with founders as a user research expert, the first few founders that I spoke with, one after another, said: ‘I care deeply about my customers, I’ve spoken with dozens of them. But wow, I’m excited to work with you because now I want to add a bit of rigor to this, I didn’t get much out of these conversations,” says Mellinger. 

These are the folks who go out without a plan, fail to check biases and often don’t think carefully about who they’re interviewing. Even after potentially hundreds of conversations, these founders emerge from interviews with little substance. Sound familiar? 

“If you’re going to put time and effort into having these conversations, you might as well not waste them. It’ll probably take more time than you'd like, but doing it right saves you from having to course correct down the road.” Enter her playbook for early-stage idea validation.

She gears her advice specifically for founders — because they’re likely the folks embarking on this early research. Nor is she advocating to bring in a UX researcher from the very beginning. But you can (and should) establish healthy habits long before spinning up a dedicated UX team.

Often, by the time companies bring in a more dedicated UX research practice, it’s at the stage where they’re asking: Did we build this well? But the real power in this research is doing it as early as possible — to actually help shape where you’re going. 

In this exclusive interview, Mellinger walks through each step of her customer discovery process in depth, starting by laying the groundwork for all that’s to come with a thorough research plan that narrows the scope of who you’ll talk to and what you’re trying to learn.

She then moves on to the user interview process itself, offering tactical advice on how to ask better questions, avoid bias and open up space for unexpected answers. And in step three, Mellinger walks us through her tested process for reflecting and analyzing all the different bits of insights you’ve gathered over the course of each interview. Along the way, she flags plenty of common mistakes to look out for in each phase. 

While Mellinger’s approach brings more structure to the customer discovery process, it’s quite beginner-friendly (and can even save you time) with tips like conducting “mini research sprints” or her template for 5-minute debriefs. 

Whether founders are toying around with a new startup idea or years into building a multi-product business, understanding user needs is essential for success. Let’s dive into Mellinger’s tactical guide. 

PHASE 1: FORM A RESEARCH PLAN

You’re bursting with excitement about your product idea and can’t wait to tell other people about it. But before charging full-speed ahead into reaching out to potential customers and setting up meetings, Mellinger suggests taking a pause. “Planning your research takes more time than you’d like, but when done well, it will save you ample time later,” she says. Otherwise, you’ll end up with a scattershot of insights, without any clear throughline tying them into actionable data. 

Even just a bit of forethought and upfront planning can completely transform your approach. To start, she encourages folks to approach their user research by chunking it down into sprints — focusing on just 5-8 narrower conversations at a time. Why? Because when you’re starting to dip your toe into user research (particularly for products that don’t even exist yet) there’s an incredibly long laundry list of things you’d like to learn. But you don’t have unlimited time with your interview subjects. 

This sprint approach to research enables you to narrow your focus — like on a particular ICP or a single hypothesis you want to validate — for the entirety of a sprint, before moving on to the next sprint with a new piece to focus on validating.  

It’s so tempting to want to ask about 10 things at once, but that’s only going to yield shallow, inch-deep responses. This is your opportunity to go deep. What are the one or two things you must learn now?

She boils it down to a couple easy easy steps (and to put these ideas into practice, Mellinger sketches out a hypothetical example of a founder who has an idea to make a brand-new kitchen tool: a frying pan that heats in half the time of a traditional pan). 

Narrow it down to: What decision do I want to make next? 

“This is often the question that we skip over, and it’s actually a lot harder to define than teams expect,” says Mellinger. “What is the next decision I want to make or the next action that I want to take with what I’m building?” 

The key here is to get incredibly narrow. For our hypothetical pan example, the ultimate decision the founder wants to make might be whether they actually should build the fast-heating pan. But for a research sprint, this is far too broad. Zooming in, a few key questions to define first are who the right chef is for the product, and what the main value proposition is for that particular chef. Or, what are the most important features to build first? 

A common mistake Mellinger sees here is trying to ask too many different things at once. “When you try and ask 10 different things, you lose the opportunity to go deep, and those variables can start to conflict with one another,” she says.

One of Mellinger’s top strategies for narrowing down the decision to focus the research sprint around is to mentally place yourself in the debrief meeting a few weeks later. What do you hope to have gleaned from the research to take into that debrief meeting? 

Prioritize quality over quantity with your interviewees 

While talking to as many people as possible may sound like a strategy for success, Mellinger has a contrarian take here: Less is more.

“If you talk with too many different types of people — even with the same set of questions — you’re going to probably get some conflicting feedback. Of course, you want diversity of opinion, but talking to people who have such disparate needs unfortunately means that only some of them are who you’re going to want to serve.”

To avoid drowning in all the noise, the mini research sprint approach comes in handy. Start with just 5-6 people. If you’ve narrowed down a target customer type enough — and pair that with a strong central decision and some learning goals — you can glean more qualitative data points and patterns from five deep conversations than from 50 unfocused ones. 

“We get nervous when we hear, ‘Oh gosh, I only spoke with five people.’ But that’s my user research magic number. If you bring that focus into it, you can get something that’s much deeper than you’d ever expect,” she says.

To find that customer type for your research sprint, Mellinger recommends focusing on two dimensions: 

• Psychographics: This is how people behave and think. In the pan example, Mellinger’s counsel would be to target chefs who value innovation and speed — as these are the types of end users that would likely invest in a pan that does the job quicker. 
• Demographics: These are the easier details to pinpoint (think age, geography, years of experience) and make up the second step of the evaluation process. Thinking back to the fast-paced, creative chefs, it would follow to target major hubs like New York City — where kitchens are crowded and the restaurant industry is competitive. 

If there’s more than one target group for your product, try five interviews with each. Narrowing your sample as methodically as possible ensures a product that’s not only good, but good for those who need it most. 

PHASE 2: LEARN WITHOUT LETTING BIAS CREEP IN

Armed with an in-depth plan, founders and startup leaders are ready to start sitting down for interviews. But this eager mindset can get plenty of well-meaning folks into trouble — this isn’t just an opportunity to hear how great your idea might be. It’s an opportunity to hear the daunting points, too.

Remember, you want to learn the scary things when you’re conducting research — that’s how you avoid spending all of your time developing a product, only to find out that no one wants it. 

Mellinger shares her tactics for how to make the most of each conversation, while artfully dodging common biases that crop up along the way. She also shares the exact interview framework structure she prescribes to the founders she advises.

Collect better data by checking your bias

Bias is pesky and persistent, especially in the interview process. While it may be impossible to completely shed inadvertent feelings and opinions, placing them behind a mask of well-structured questions is a must if you want real feedback. 

“It’s not that people are trying to deceive you,” says Mellinger. “But bias from both ends can unfortunately create an environment of false signals. All of a sudden you’re building something that people don’t want as much as they indicated.”

Mellinger notes three types of bias to avoid when conducting user research.  

Confirmation bias: Put earmuffs on your “happy ears”

The more you have at stake, the more that you’re probably listening for what you want to hear.

When you’re asking for feedback, don’t only listen for the things that sound good. Make space for the things you don’t want to hear — those are the ones that’s what will make your product better.

With the right framing, everything can be interpreted as a green flag. You think making a faster-heating pan is a great idea, so no matter what happens over the course of the interview, you’re predisposed to leave thinking the other person agrees with you. 

The primary culprit that allows confirmation bias to flourish is how you phrase the questions. To avoid falling into the positivity trap, cut out leading questions.

“A leading question is one that we already have an answer to in our minds,” says Mellinger. “We’re not so much asking it to get new information as we are to validate our own thinking.” 

Certain nuances of language have the power to compel people to answer a certain way. Take a seemingly innocuous question like: “Do you think this is easy?” or “Do you find that difficult?” “We’re implying that it should, in fact, be easy or that we do think that it’s a struggle,” says Mellinger. Even if the interviewee doesn’t feel that way at all, the question’s tone can steer them away from their true experience. 

When structuring questions to avoid confirmation bias, Mellinger uses a few key strategies:

• Avoid ‘yes or no’ questions. If your question can be answered with a simple yes or no, that’s a big red flag that you’re asking a leading question. In user research interviews, questions like these almost always start with, “Do you…” On top of their leading nature, they also lead to a less rich answer than when you ask, “Tell me about X, Y or Z.” 
• Be careful with adjectives. Another hint that you’re headed towards a leading question? Sprinkling in any sort of adjective (like “easy”). If there’s an adjective in your questions, there’s an implied opinion. Instead, try rephrasing to a more neutral position: “Tell me about this experience…” 
• Course-correct with follow-ups. While it’s best to avoid adjective-laden questions altogether, there may be times when you can’t escape asking something a bit more pointed. In that case, Mellinger has two tips. First, give the interviewee an out: “To what extent was this easy if at all?” Next, follow up with the counter: “To what extent was this difficult?” to balance the scales. 

Let’s say you start to hear something that sounds really good. That’s your alarm right there. The moment you hear, “Oh yeah, this product is great,” that’s a sign to ask the counter. What is something you can push on here? 

Acquiescence bias: Dodge attempts at people-pleasing

This particular strain of bias starts from a pretty lovely (but not all that helpful in a research setting) sentiment that we as humans are inclined to be nice to one another, and try to make other people feel good or hope that people will feel good about us. So when conducting customer research, the less you reveal your hand the better. 

The more we signal the ways in which we want someone to answer, the more they want to make us feel validated.

Mellinger’s solution is straightforward: hold off on talking about the product. This allows you to get a better read on what’s most important to the person before they inadvertently jump into the mode of being helpful to you.

Introducing acquiescence bias into your user research can start as early as the subject line of your recruitment email. “Hold off on talking about your product. You want to share a least a little bit of information about who you are and whom you want to speak with, but minimal information when you can about what your product is,” says Mellinger. 

“You can say: ‘I’d like to speak with chefs who are working in a busy kitchen and want to learn how to maximize their time in the kitchen.’ But you don’t need to say, ‘I’m trying to build the fastest-heating pan,’” she says. 

Otherwise, your conversations will center around frying pans — even if it’s not all that important to them. “Once they figure out you’re interested in pans, they’re going to want to talk to you about pans — even if they could care less about pans. But what if there was something else that was really concerning to them outside of pans?”

And once you sit down with folks, it can be equally tempting to ground the conversation in the context of your product idea. Think starting the interview off with: “I would like to talk to you today about pans.” But instead, Mellinger suggests a more open-ended opener. “Most of the talking I do as a user researcher is at the beginning of the interview, and a lot less later on. So in the beginning, I’d say, ‘Hey, I’m Jeanette, I want to learn more about how you operate in the kitchen. I’m going to eventually show you an early idea, but for now, I want to better understand you and your world. So anything that I ask you, feel free to elaborate on what’s most true for you. And you don’t have to answer any questions that you’re not comfortable with.’”

Here, Mellinger also has one unexpected tip. “It sounds a little silly, but I start these conversations by putting my hand into a fist on top of my head and tell them that I want them to talk as freely as if they have a microphone on their brain,” she says. “It's so out of the ordinary for people that it makes them pause. And it will come up later in the interview — they often repeat back to me, ‘I guess if I had a microphone on my brain, I would tell you X, Y, Z.’ It’s something they wouldn’t have otherwise felt like they should share.” 

Hindsight bias: Ditch the crystal balls

As founders know (often a little too well), predicting the future is all but impossible. Yet, in user interviews, it can be tempting to ask questions like, “Would you use my product?” or, “How much would you pay for this?” While you may get some educated guesses, they’re impossible to bank on. So Mellinger underscores that it’s best to rely on the strongest predictor of human behavior: past behavior.

“In the pan example, I’d ask questions to find out how much they’re investing in kitchen tools now, how they've thought about that and how that’s changed over time,” says Mellinger. That’s a much more resonant indicator of how they might weigh pricing decisions in the future.

Another tip if you really want to hone in on pricing: “Come up with an obviously very high number, say $1,000. Watch that person’s reaction, and you might just get an interesting off-the-cuff answer like, ‘No way, I’d never spend more than $150 on a pan.’ And boom, there’s your price point.”

Structure the time: Discover the unexpected by zooming out, in, then out again

Even expert user researchers who are questioning pros would never wing it when it comes to sitting down to an interview. Taking a little bit of time to game out how you’re going to structure the time can mean the difference between a meh conversation, and unlocking unexpected insights. 

Across the board, whether you’re conducting research for a brand-new idea or gathering feedback on an existing product, Mellinger prescribes the zoom out, zoom in, zoom out framework. 

Practically speaking, you begin the interview by zooming out on the bigger context into the space and the person to whom you’re speaking. Next, zoom in to more specifics about your idea and problem space. Finally, wrap up by zooming out once more with some higher-level questions. 

To put these ideas into practice, Mellinger shares an example from a real-life startup she teamed up with. “I was working with a team that wanted to serve small businesses by building their online presence, specifically through Instagram. For them, the ‘zoom out’ looked like getting an understanding of how people ran their businesses in general. Zooming in a little bit more, I had them ask about digital strategy more broadly, including how they’ve built the online presence for their business. What social apps did they have a profile on? It took most of the interviewees a while to even get to Instagram, but that allowed us to learn some things about YouTube and its problems, and that gave us a completely different — and probably better — window to explore.”  

The final ‘zoom out’ is an opportunity to contextualize all your findings. Asking the customer, “If you had a magic wand to fix X problem, what would you ask for?” allows them to revisit what’s most important to them. It could be something completely different from the zoom in, or it could confirm everything they said before.

This is a marked difference from how that same team had initially been approaching user interviews. “Before we were working together, they often led in their recruitment emails with, ‘We're working on making Instagram easier for you.’ They'd start their interviews with, ‘We want to make, Instagram easier for you,’ and then dive right into the interviewee’s feedback on Instagram.” This pointed approach didn’t leave any room for the interview subject to talk about other platforms that might be giving them trouble and that were a deeper pain point for them. 

Practical tips for asking better questions

With that framing in mind on avoiding bias and structuring your time with the interview subject, Mellinger shares her punchlist of two tips for asking stronger questions.

• Ask one short question at a time. Humans tend to offer a lot of preamble. When asking questions, we jumble two or three together in hopes of getting more out of the recipient. In reality, this kind of structure often lends itself to the exact opposite. Give people the space to answer in a nuanced way instead of forcing them to try and remember a handful of different queries. “This is something you can even start practicing at the dinner table tonight,” says Mellinger.  
• Ask each question two to three different ways. This is especially important if a question is particularly important to you. Even if you feel like you got good information out of the initial ask, try reframing the question to see if you can discover any kind of new insight. As Mellinger sees it, probing at from different angles can help uncover all sorts of data points. 

PHASE 3: FIND PATTERNS IN THE ANALYSIS PHASE

The end of customer conversations is far from the end of the research process. You’ve now got dozens of (possibly conflicting) bits of insights and data from your user interviews. It’s time to piece it all together. While all the information may be collected, the real findings come from taking a look back. 

Here, Mellinger prescribes a three-pronged approach: short analysis after each call, hour-long weekly syncs, and longer comprehensive analysis. 

But before diving in, the first thing to nail down is your documentation hygiene. 

It’s impossible to store every bit of insight in your head — that’s why Mellinger recommends recording every single interview. That way, even if the feedback isn’t relevant right now, you’ll always have a transcript to refer back to. But a raw transcript alone isn’t enough, because it’s unlikely that you’ll have the time to listen back to every conversation. So she also recommends a note-taking template (and ideally, bringing in another person to act as your note-taker). 

“As I take notes, I’m jotting down any quotes that either confirm or disprove my hypothesis, as well as any strong emotional reactions. I might put an “H” next to something related to my hypothesis, or an “E” next to a big emotional response. It will make your life easier later on, because you’re going to get hundreds of pieces of qualitative data in the interview. This practice will make sorting through everything much easier later on,” says Mellinger.

With your notes in hand, here’s how to proceed with the three-pronged analysis approach.

The short version: have a post-game 15-minute huddle 

After every interview you conduct, Mellinger recommends putting 15 minutes on the calendar with your co-interviewer (like your co-founder, if they also sat in on the call) or notetaker. “This practice gets people a lot further than they think — it will make your later synthesis so much faster. It’s tempting to schedule back-to-back calls, but it’s so much better to debrief when it’s fresh,” says Mellinger.

This is a space to share initial thoughts and reactions, particularly related to three key topics:

• Data: During this huddle-up, write down any piece of data that stood out. Mellinger suggests specifically looking for things that both supported and countered your original hypothesis. Successful interviewers are able to recall both what a customer said (direct quotes) as well as what they showed (think body language, tone, a big audible sigh). 
• Insights: Insights are the early interpretations of what’s going on. Look at the data you’ve collected and translate that into a general sentiment. Ask: “What patterns am I starting to see? Is that my opinion, or is that the story the data is telling?” 
• Action: To wrap up this short debrief, address at least one actionable item that can serve as a next step. What’s one bit of insight you want to follow up on in your next interview? Do you need to change any of the questions to better avoid bias? Whatever it is, move forward with not only reflections but concrete to-do’s. 

You don’t want to draw any conclusions after only one call, but it’s okay if some high-level takeaways start forming.

The medium version: block out an hour-long weekly meeting

The next step from the huddle is a more formalized, recurring meeting to synthesize your findings across multiple conversations — like at the end of a 5-interview research sprint. Mellinger finds these medium debriefs particularly useful for sharing your findings more broadly with the team — who may not be sitting down with you for each of these interviews.

“On Friday mornings, we put an hour on the calendar to synthesize what we learned that week,” she says. “This is where all of those shorter debriefs become helpful. You don't have to go back and reread all the transcripts, you just need to look at the follow-up notes and pull out the highlights,” says Mellinger.

This is also an open space to start throwing around the ‘whys.’ Why does a customer do X? Why is that important to them? These types of questions start to bring out the patterns across different user answers. 

The longer half-day version: systematically look back at all of your interviews 

This version of analysis is not dissimilar to the evidence boards seen in crime shows and murder mysteries — with pins and strings interconnecting to form a complete picture of the case. 

“The goal of this stage is to look back holistically and see if there’s anything that wasn’t captured in your shorter debriefs,” says Mellinger. “After you have everything laid out properly, start to clump those pieces of data together and see which ones relate to one another. That’s where you begin to see the patterns that emerge.”

She recommends the affinity diagramming method, where you put a bunch of post-its on the wall, each representing an insight from a user interview, and start clumping them together to see which ideas relate to one another. 

If you’re not quite ready to level up to affinity diagramming, that’s okay, says Mellinger. “At least try incorporating the small and medium analysis into your process,” she says. 

So often teams will want to jump right into solutioning and action mode. But the more you ground yourself in the data, the more conviction you’ll have in your idea.

WRAPPING UP: FIND SUCCESS BY BEING INTENTIONAL 

Successful user research strikes the balance between speed and patience. While it’s important not to start the process too late, taking the time to get a strong understanding of the findings is equally crucial. 

You have to think about user research from the very beginning — you can’t be slow to get there. If there’s a lack of rigor around investigating customer experience at any point, you’re doing your product a real disservice.

“Moving too fast makes you miss the root cause of the problem,” she says — pointing to the famous (if disputed) Henry Ford line. “That means you don't need to take everything that customers say at exact face value. Ask yourself: ‘Why are they asking for a faster horse? What’s going on here?’ The more you ground yourself in that data and synthesize, the more conviction you’ll have in what customers are really telling you.”

To make something that customers love (rather than a product that quickly fizzles out and fails to find product-market fit), set out early to deeply understand the customer ask and where it’s coming from — even if that requires a little more time and nuance up front. 

No founder’s journey to product-market fit is straightforward — all you have to do is peel back the layers. Even company-building voyages that appear, on the surface, to be relatively linear turn out to be riddled with challenges, from painful pivots to rejections to long stretches of uncertainty. 

However, few paths are as winding — and fascinating — as Eddy Lu’s. Today, he’s the co-founder and CEO of GOAT, a global platform for sneakers and luxury apparel that boasts over 350 brands, a million sellers, and 50 million members across 170 countries.

But Lu’s journey to getting where he is today was marked by dozens of inflection points — some that went right, some that went sideways. All of which, when collapsed together, formed GOAT’s enthralling path to product-market fit.

So what exactly happened over the course of the decade it took to build and launch GOAT? Hint: it involved a venture in cream puffs, a pair of fake Air Jordans, and a physical altercation on the basketball court. 

To get the full story, we have to rewind to the mid-2000’s. 

EXPLORING IDEAS

In 2005, Lu was looking for a roommate in Los Angeles. As it turned out, Daishin Sugano — a friend-of-a-friend Lu had played basketball with a few times — was also on the hunt for a new place to live. They decided to become roommates. 

While living together, Lu and Sugano were feeling stagnant and unfulfilled in their corporate jobs and began toying with the idea of teaming up to start a company. “We talked about building something together every single day until, in 2006, we were finally like ‘Hey, we’re not going to figure out how to start a business while working these demanding jobs, so why don’t we just quit?’”

And that’s exactly what they did, kicking off a new era of entrepreneurial endeavors. 

Cream puffs

The first venture Lu and Sugano pursued was becoming franchisees for Beard Papa’s — a popular cream puff establishment with a large presence in California. “The plan was to buy a few chains and have a manager run everything,” says Lu. 

They opened their first store in 2006, and subsequently two other locations in the couple of years that followed. But after the 2008 financial crisis hit, Lu and Sugano were forced to close two of the three locations.

iPhone apps 

In 2008, Apple launched the App Store. Given Lu’s degree in computer science and Sugano’s design background, they figured, why not build a few apps to make some money? 

“We developed some of the very first iPhone apps in existence — like to-do lists and simple games that cost $0.99,” says Lu. 

While the apps saw moderate success, none of them took off in the way they had hoped. 

GrubWithUs 

In 2010, Lu and Sugano moved to Chicago to try salvaging and expanding their remaining Beard Papa’s location. As lifelong Californians with few connections to their new city, the transition was tricky for both of them.  

“We realized how hard it was to make new friends. That’s when we started thinking: what's an easy way to meet new people?” And that’s how they came up with the idea for GrubWithUs, a social dining app for sharing meals with strangers. Folks could reserve a seat at a table of a participating restaurant, and if four people reserved a seat, the date would be set for the once-strangers to socialize over a shared meal.

With this idea in hand, the co-founders applied to Y Combinator and were accepted in 2011. Soon after, they raised a $1.6 million seed round from a group of investors, (including First Round Capital). A $5 million Series A followed in 2012. But despite the early excitement and an influx of cash, the app just wasn’t taking off. 

“Think about all the friction points in that kind of marketplace. People are thinking: What if I’m vegan, and there are no vegan options at the restaurant? What if the restaurant’s too far and people don’t want to travel out of their way? And then there’s the social aspect of having to socialize with strangers. So that social friction, plus all the other friction points, made it impossible for that marketplace to function,” says Lu.

PIVOTING

In an attempt to salvage GrubWithUs, Lu and Sugano knew they needed to pivot. But, as Lu explains, there’s a wrong way and a right way to pivot — as the co-founders, unfortunately, found out the hard way. 

The wrong way

“We tried to create a new startup using the existing restaurant data we had. But honestly, we were just trying to save face with our investors. If you had asked us if we were passionate about building this next idea, we would have said no. We were just trying to salvage the scraps that we had,” says Lu.

What makes pivots so pernicious is that it’s easy to get stuck in a vicious cycle of the sunk cost fallacy — you’re loath to let go of everything you’ve worked on, so you end up creating iterations of the same idea that didn’t work in the first place. This is the unenviable cycle that Lu and Sugano found themselves caught in, as their runway continued to shrink.

So the co-founders forged ahead anyway, and ended up wasting months building something they didn’t care deeply about. And sure enough, when the new company finally launched, it failed. 

The better way

Amid these panicked attempts to pivot, there was a bit of bad luck that turned into an unexpected lightbulb moment.

“Daishin is a lifelong sneaker enthusiast, and he got his first pair of Jordans when he was 10 years old. In 2013, that same shoe — Air Jordan 5 Grapes — was re-released. So, of course, Daishin went on eBay to snag a pair,” says Lu. 

Even though Sugano put hours and hours of research into choosing what seemed like a legitimate eBay seller, he ended up receiving a fake pair. While he was, understandably, pissed off, it sparked a new idea. 

It raised a question in our minds: how come, in this day and age, we have hundreds of options for purchasing sneakers online but still have to worry whether something is real or fake?

To Sugano and Lu, it was obvious that there was a need for a sneaker marketplace where everything was authenticated. And that’s how they stumbled upon the idea for GOAT. 

Even though they were excited about the kernel of an idea (much more so than their previous venture), Lu and Sugano were nervous about presenting such a dramatic pivot to their investors. They first approached Greg Bettinelli, a partner at Upfront Ventures with a lot of marketplace experience.

After hearing their pitch, Bettinelli was convinced of the new idea and gave Lu and Sugano the green light to drastically change course. So the co-founders got the emotional buoy they needed to email the rest of their investors, who encouraged them to keep their remaining money and go for the pivot. Looking back, Lu says that this approach to pivoting was clearly a better one. 

You need passion, a solvable problem, and luck: That’s the equation for pivoting.

BUILDING

At this point, Lu and Sugano only had around $1 million left in runway. So they knew they needed to build and validate their authenticated sneaker marketplace idea, fast. 

Based on existing eBay data, they decided their stretch goal should be to sell 100 sneakers per day. But they faced the cold-start problem. 

With marketplaces, there's a whole chicken-egg problem. If you have no sellers, there’s nothing for people to buy. With no buyers, sellers don’t want to sell anything on your platform. So we had to hack one side of the equation.

What the co-founders ended up doing was buying a small number of sneakers and putting them up on the platform. But to make it seem like their stock was more robust than it actually was, they had to get a bit creative. 

“If you looked at eBay, people were taking pictures of their sneakers on the floor to sell them. So at Home Depot, we went to the flooring section and bought different types of flooring — and then we photographed the same shoes on stone, wood, and laminate,” says Lu.

LAUNCHING

GOAT officially launched in July 2015 with a featured article on Complex. They made 20 sales that day which, while not a hugely impressive number, was still money made — and a milestone to celebrate. 

That is until, two weeks later, Lu and Sugano received 11 chargebacks. So instead of making money after launching, they lost money. Sales were sluggish until Black Friday of that same year, which is when things changed drastically.  

“Our Head of Marketing wanted to do a Black Friday promo. We only had tens of users at that point, so we were like, ‘Sure, do whatever you want.’ So as a Black Friday event, we decided to discount the hottest sneakers of 2015 to retail prices.” 

For a bit of context: sneakers are one of the few marketplace items that tend to increase in Gross Merchandise Value (GMV) over time — and this was the year that the Yeezy line launched. So the fact that GOAT was going to sell sneakers valued at over $600 for the original retail price of $200? That was a big deal in the sneakerhead community, even though the co-founders didn’t quite realize it at the time.  

The result? Every single publication in their industry wrote about the promo and, as a result, GOAT had a massive influx of users on Black Friday that crashed their site. They went from having tens of users to over 100,000 in one week.

While this might sound like a dream, it ended up being a nightmare for the co-founders. Between the failing website — and the fact that they actually only had 50 pairs of shoes in stock for the promo — users were deeply upset. So angry that some people directly attacked Lu himself, leaving him nasty comments on social media. 

“People had skipped work, school, and even doctor’s appointments to be online for our Black Friday drop, and they were upset when the site crashed. We had to apologize profusely,” says Lu. 

What was unusual about GOAT’s predicament was that, while they were certainly in the midst of a crisis, this was also their ‘aha’ moment — the surefire signal that they found product-market fit. But it was difficult to recognize the significance of that moment when people were sending Lu expletive-loaded messages. It was Bettinelli who gave the co-founders the perspective they needed: 

In that painful moment, we got advice that I’ll always remember: At our company’s stage, it’s better to be hated than unknown.

Turns out, this mantra was spot-on. 

EXPANDING

Despite the thousands of unhappy GOAT users, they stayed. The reason, Lu believes, is because they figured out what GOAT was trying to do — authenticating sneaker purchases — and believed in the idea enough to give them another chance. 

So despite the initial hiccups, sales skyrocketed after Black Friday. During their period of hypergrowth, Lu and Sugano made sure to keep all the lessons from their past failed entrepreneurial endeavors top of mind. 

PMF Lesson #1: Prioritize reducing friction

One of the most controversial decisions the GOAT team made in the early days was the way they decided to display their products.

Let’s say, for instance, you were searching for a pair of Yeezy Slides in size 6 in the color onyx. On eBay, you would see dozens of listings from different sellers who are selling that exact product. On GOAT, you see the shoe and, below that, the seller who had the best price, fastest shipping time, or a reduced cost due to small defects.

When GOAT rolled out this feature, it caused a big uproar because it changed the way people shopped for sneakers. Lu and Sugano even had some big players in the industry tell them they were making a huge mistake. But they stood firm by their decision, based on what they learned from their time building their last company. 

“With GrubWithUs we learned that friction can kill marketplaces. On eBay, you could have 300 sellers who were listing the exact size of shoe you were looking for, and you would have to sort through ratings, comments, shipping information to find exactly what you need. We wanted to remove that friction from the experience. And since we’re an authenticated marketplace, people could trust that they would receive exactly what they ordered,” says Lu. 

PMF Lesson #2: Don’t rush

Today, GOAT sells both sneakers and luxury apparel, and the company has a massive international presence with 17 authentication centers around the world — from Malaysia to Berlin. But the process of expanding even from sneakers to apparel took close to five years, says Lu. 

“Again, it was because of our painful lessons from GrubWithUs,” Lu says. “Shortly after we launched, we decided to expand to 12 new locations — even though we didn’t have the internal infrastructure or product-market fit — because we knew that any time we opened up in a new city, we were going to see an uptick to gross merchandise value. Instead, we went from having one problem to 12 problems, and then everything fell apart. So with GOAT, we wanted to do it right. We wanted to focus, win in the sneaker industry, and then expand.”

ON COFOUNDER RELATIONSHIPS

While much attention is, rightfully, paid to the process of zeroing in on the idea and building from 0-1, Lu urges founders to pay just as much attention to de-bugging the co-founder relationship. In fact, it’s the reason why many companies fail before they even have a chance to take off. 

This isn’t to say that even highly functional co-founder relationships won’t have their fair share of conflict. While he and Sugano have been business partners for over two decades now, he admits that there have been a lot of tense moments. One, in particular, stands out in his mind. 

“We went with our friends to go play basketball,” says Lu. “We ended up on opposite teams, guarding each other. As the game went on, we got increasingly physical and aggressive with each other. During one play, I practically picked him up and threw him on the ground.”

This evolved into a full-blown physical altercation, where Lu and Sugano had to be separated by their friends. You might imagine that this would sour the relationship — at least for a little while. But after they got in the car, Lu remembers: “We just looked at each other and were like, ‘OK, let’s get back to work.’” 

The lesson being: Even in the strongest co-founder relationships, things will get tough. Emotions run high, stress bubbles over, and you have intense disagreements. But, as Lu explains, you have to be able to put these things behind you and move forward together as a team. 

LOOKING FORWARD

With GOAT, Lu and Sugano have completely changed the way people interact with sneaker culture and high-end fashion. And, as evidenced by the fact that they raised their Series F in June of 2021 at a nearly $4 billion valuation, there are no plans to slow down. 

The secret, according to Lu, is to have unrelenting grit and an unshakeable belief in yourself. At one point while building GrubWithUs, some investors had even urged Lu and Sugano to find a way to get acquired. It went as far as taking a few meetings with potential companies that might be good landing spots.

“But at one point, we just looked at each other and were like, do we really want to go through with this? Are we burned out? Are we sick of each other? And the answer was no — we weren’t ready to throw in the towel. We wanted to keep going,” says Lu.

“It’s not about building the best product. Being the best means nothing.” For product builders striving for perfection, these words might not seem particularly motivating, but for Tara Seshan, this advice is a phrase she returns to whenever she’s considering where to place a new product bet.

Before her most recent role as Head of Product at Watershed, Seshan spent a nearly seven-year stretch at Stripe. She joined the company at the sub-200-person mark in 2015, back when “there was still very little adult supervision” as she puts it. 

Seshan spent a year of that tenure with Shreyas Doshi as her manager, from whom she picked up this lesson originally. “Everyone always overestimates the impact of launching specific features and building the best product, but that’s not the answer — you have to build the right product for your target user,” she says. Sounds simple in theory, but tough to consistently pull off in practice, particularly as a scaling startup takes bold swings at building out its product lineup.

Seshan makes an excellent guide on this topic, as she has a deep well of experience to draw on here. She was the PM on Radar, Stripe's first monetized product outside of core payments, and she helped scale Billing and Treasury from 0 to 1 as a product lead and GM. 

In this exclusive interview, Seshan shares nine lessons from her playbooks for going multi-product, drawing on examples from both Stripe and Watershed. From advice on how to get the timing right and different ways to approach the problem of what to build, to tips for hiring great product thinkers and the specific steps she uses to run effective product reviews, founders and product leaders alike will walk away with tons of put-to-use tactics.

LESSON #1: Choose carefully from the multi-product menu

When Seshan joined Stripe in 2015, it was a one-product shop. “It was the core payments API, we hadn’t even launched any other payment methods out of beta yet,” she says. But the journey of moving from a single product to a wider array of offerings isn't as simple as bolting on new features or spinning up new teams — it requires a carefully chosen strategy. Here’s the menu of options, along with the pros, cons, pitfalls to watch out for, as well as insightful anecdotes from Stripe:

Same customer, same buyer

“If your product has initial product-market fit for a core user, what else does that specific user want that would make their job better? Think of the classic line that your B2B buyer wants to get promoted — what can you give them to help make that happen?” says Seshan. 

“When Stripe was thinking about second products, one of the easy angles was asking first, Who is our buyer? It's that developer who's integrating payments early on. And second, what could you give that same buyer to make their lives meaningfully better?” she says. “One thing that sucks about taking payments on cards is fraud — and so that's how the fraud product, Radar, came about. We were able to narrow down the set of features that made a difference for that same user.”

It can be really fruitful to sell something else to your same buyer. You know that user and you know their needs. You’re much more likely to succeed by giving them an additional product rather than trying to launch a product that targets something wholly new altogether.

Same customer, different buyer

That laser focus on the customer can quickly turn into blinders, however. “There were several products that we thought were the same buyer that turned out not to be,” she says. Seshan cites the origin story of Stripe Billing, a suite that consists of subscriptions, invoices, revenue recognition, and SaaS metrics. 

Seshan spearheaded the product’s launch in 2018, but it wasn’t a resounding success initially. “We had naively launched it with this idea that the same person who was integrating an API for one-time payments was going to be the same person integrating and evaluating an API for recurring payments,” she says. 

Developers were still involved in the decision, but they weren’t the sole decision-maker anymore. “We were selling to larger and larger companies over time, and those users were growing up. We had customers like Notion and Figma, and we had just under-accounted for the fact that the initial buyer and user would not be the same when the company hit velocity. At Figma, the customer we talked to on a day-to-day basis went from an engineer to their VP of Finance,” she says.

“And so we were making a bunch of product decisions from first principles but it absolutely didn't make sense to reinvent accounting to make this product work. We had a sales team staffed up against this product, and folks weren't hitting quota because they were now selling to this finance buyer even though we weren’t meeting their needs. For example, our invoices used to be stateless, and now we had to have a state of paid, unpaid, or in progress. It required a ton of reexamination of the product, with extensive migrations and refactors. We got there after a little while, but we had to change our approach.”

New customer entirely

But new product ideas can spring from entirely new wells. “The other dimension of thinking when you’re going multi-product is if it allows you to unlock a net new user base that you weren't targeting before.” Seshan cites Stripe Connect as an example here.

“We were targeting folks who were taking, for lack of a better term, ‘vanilla payments,’ so we started to think about a tool that could take on more of the complexity for those building a marketplace business — the underwriting of initial accounts, the routing of payments, the balance calculations.”

LESSON #2: Tease out your vision and focus on making the “why now” case

Timing is perhaps the trickiest part of figuring out your multi-product strategy — how do you thread this needle? “One school of thought is we’re way too early, just focus on the core, that’s the most important part of realizing our vision. Or you can make the call that the vision requires a couple interdependencies to exist, which means you have to staff it earlier than you would otherwise,” says Seshan.

Both Stripe and Watershed have approached this crossroads quite differently. “The engine that powers Stripe is payments. It's always going to be payments. And so Stripe didn’t — and should not have — overreached into multi-product before payments was really, really, working — at the level of we were fending off leads and letting them fall on the floor,” she says.

“And in contrast, Watershed had to invest in multi-product really early in the company’s life cycle. But we had to do it early because we thought that the future is integrated carbon accounting and decarbonization tools — you need to have both to make companies effective. That vision requires that interlock. And so we weren't batting leads down before we invested in a new bet.”

With either path, however, there has to be a compelling answer to “Why now?” Seshan says. “What makes this idea something we have to do now, something we can't do later? Is there a unique at-bat for it at the moment that makes this something we have to jump on?”

When it comes to a second product, there are so many things you could build that there has to be some intersection of the moment and the opportunity.

The stage of your company, of course, also plays a role here. “As Stripe got larger and larger, the question became not only why now, but also ‘What's the opportunity on the table for this idea?’ Patrick’s bar was, ‘Is this going to add $10 billion of enterprise value to Stripe? Could you paint for me a path where that could happen?’ He would always remind everyone that Stripe has 9 million opportunities in front of it — why this opportunity and why now?” says Seshan. “At a much earlier stage for Watershed, it was instead a question of how costly is it to develop an initial hypothesis? How lean can we go and how fast will we know if it is or isn’t working?”

LESSON #3: Think through whether you’re making calls on analytics vs. instincts when you’re trying to score new runs

Digging deeper into the question of when to launch a new product, Seshan notes that there are two different approaches:

“The methodical answer is that there are only a few ways for a company to grow: 1) expand into a new market via going into new countries, 2) expand into a new market via going into a new product area that sells to a new buyer, 3) capture more TAM by selling more to your existing buyer or 4) raising your prices,” she says. “From a very analytical lens, you’ll pick among those options based on how the product is resonating in the market today, the willingness to pay of our buyer, the potential advantages we have on adjacencies or how the geographic landscape is looking. Stripe often takes that very analytical approach and Patrick thinks backwards when you put a bet in front of him.”

“But consider the early story of Cash App, which seems to be the exact opposite. Jack Dorsey had an intuitive belief that people needed payments to work this way and they needed to empower the masses to be able to bank when they're underbanked. And so they kept plugging at it for years and years. And now look at how successful Cash App is and what a giant part of Square’s business it is. So instinct can be a huge driving factor in figuring out when you go multi-product.”

The analytical approach will get you a lot of singles and doubles. But the home runs really come from those intuitive calls on how you think the market and the world is going to work and betting in that direction.

LESSON #4: Bring a dose of definite optimism to your thesis

“Particularly when you’re in a really early, developing market, the important thing is to have a view of what you want the future to be like. There is the Peter Thielism of definite versus indefinite optimism,” says Seshan (a Thiel Fellow, we'd note). 

“You need very definite optimism about how you want the space to shape up. For Watershed, here’s what that looked like: In 10 years every public company will need to do some level of carbon accounting and have a decarbonization plan to underscore that. And the best way for companies to decarbonize is through their supply chain and through buying clean energy. You have to have a very strong thesis for exactly what the future is going to look like, and feel like your product investments are making that future happen in the near term.”

You are both riding the wave and manufacturing the wave at the same time. You're placing bets to hit near-term goals, but more importantly, to feed the long-term outcome of your vision.

LESSON #5: Keep it lean by assembling self-sufficient business units

Figuring how many eggs to put in each product basket is another challenge teams grapple with. Seshan’s rule of thumb? Initial secondary bets outside the core can't be expensive.

“At Stripe, core payments took maybe 75% of the engineering bandwidth. Part of what incentivized the early team to work so hard on new ideas was that you got very few resources. You had three or four engineers and you were trying to get a proof of concept really fast, to earn your way to more resource allocation,” she says. 

That meant, while proving out an idea, teams had to get scrappy. “For Radar, the fraud product was still built for developers, so we didn't need a ton of user researchers. I was selling and doing the product design, and then also going into our models and trying to write human-readable explanations for why the model scored things in certain ways. It took the communication coordination cost out of that initial product building entirely — until it became clear that it was worth paying that for additional velocity.”

Don’t overfund your new bets. In that early stage of trying to establish something, more resourcing actually holds you back. You want as few people as possible with the maximum number of skills.

That may seem counterintuitive, but as Seshan sees it, you want more people doing stuff than people being brought along. “You don't want the team to have strong dependencies on any other part of the company. They don't have to be great at all of those things, they just need to be willing to do it.”

Here’s how to think about it from an org design perspective: “Treat it like a business unit, full end-to-end with their own salespeople, targets, and marketing motion. Do not staff your traditional scaled seller on this. You need a founder-seller type, someone who can do their own sales enablement. The product manager might be doing sales as a part of that as well,” she says.

“‘A startup within the company’ is a hackneyed phrase now, but they should feel like their own entity. Obviously, they aren’t going out there and raising money and finding their own offices. But in some ways, they are raising money — from the rest of the company. So as the head of product or the CEO, have ‘board meetings’ where they tell you how they’re doing, just like you tell your investors how you’re doing.”

Treat the team as if you were their board and they are starting a new startup — but be a lot more hands on than a board is.

LESSON #6: Run these highly structured product reviews to stay on track

If you’re looking for ways to structure those regular check-ins on new product progress, Seshan cites Stripe's processes as one well worth adding to your toolkit.

“Of course, there’s the QBR, which is an important tool and a bare minimum level of check-in. But Stripe would also do a monthly product review to dig into the details. Specifically, there is a set of 12 questions that Stripe leaders ask in every product review. And there's a very strict guidance that you cannot move on to question two until you've sufficiently answered question one,” she says. “You don’t get to all of the questions in every review. Sometimes a team will come in and say, ‘I've only answered four, or I answered one through six in the previous review, now let's get into the others.”

The key here is not letting folks skip over some essential context-setting by jumping right into the product experience.

You're trying to build something that wins, and no one gets anything right on the first try. Software is never done and it’s always bad in the first version. But it’s very hard to evaluate it without any context.

“So these questions are mostly meant for two things: One, how do I get context? And two, let's say a team went through all these questions but then the product review was canceled. Was it a waste of time? Were they just prepping it for me? Or is it useful thinking for their actual product development? And my goal was to make it actually useful regardless. I honestly fill out these questions when I'm building something because it’s just the questions you should answer for any product.”

With that context, here are her questions in full, with commentary on what to dig into:

1. Who is the target user? “This question always brings me back to the Enterprise story,” she says. (Yes, the car rental company.) “Not sure if it’s apocryphal or a real story, but I still like to tell it. Enterprise was competing with the likes of Hertz and Avis. Those guys had the airport real estate. They also had Audis and BMWs. Enterprise Rent-A-Car really had nothing. And so there was absolutely no way to compete by building ‘the best service’ or ‘best product.’ What they did instead was focus on a different user — people who get into car accidents,” she says. So instead of focusing on providing fancy vehicles, Enterprise offered a unique crash pickup service. “Over time, they were able to expand. But it started by making a very, very opinionated bet on who their target user was and it allowed them to compete on dimensions that other services and tools just didn’t find relevant. It is the most important question to ask, full stop. If you cannot clearly outline to me who your target user is and, therefore, why the features follow are uniquely suited to that user, it’s dead in the water. It's got to be specific.”

2. What is the user need we’re solving for?

3. Can you share a link to your evidence of why that need is actually a need and not a made-up need? “Is it a problem that’s actually an issue for companies and do they feel it urgently? Does it matter enough? Is it on their list of top five things that they're worried about?”

4. How will we know if we’ve solved for that need?

5. How do we know it’s self-serve and operations-free? “That's a very specific question for the type of enterprise, strategic user type business, where it can often be easy to compensate with services, instead of what a product should be doing.”

6. What is a range of solutions to get there? “It's always easier to agree on one solution if you've thought about alternatives.”

7. How have you leveraged the company’s existing assets or advantages? “In Watershed's case, it was a ton of climate-specific intelligence and reference data. And at Stripe it was the adoption of the API, our existing user base, our payments expertise, etc.”

8. What is the intended experience from the users’ point of view? “At Stripe, I would love for people to give me API docs here so I could try integrating it myself. Or it could be showing me with a user story the requests the user makes at every step of the way.”

9. How quickly will we start learning if our solutions are the right ones? “I always ask for creative ways that people are getting at this question, especially with a net-new product that’s going to be sold to a different buyer in a totally different motion. If you're just waiting until they close their first deal, it's going to take way too long. And so the thing I dig for is, short of doing a full sales cycle — because you're going to have a lot of fits and starts with that — what are ways that you're learning whether this is the right move? Are you looking at competitor sales? Are you doing a ton of user interviewing? Say you’re selling to CFOs — will you practice selling with those ‘contract CFOs’ and see whether they find the product interesting or resonant?”

10. What are the criteria will we use to evaluate that the solution is the right one? “I like to ask what are your success metrics and let's get into a ton of details there.”

11. What will we actually build to provide this experience? “Now I know the problem's a problem, I'm going to come up with a set of principles about what the solution should look like and design a version of the solution. The classic early days of Stripe are a great example. There was a strong belief that giving developers autonomy and letting them design on their own was the right model and solution.”

12. What is the plan to build it? “What's the work to be done? The operational model, any risks or open questions, and so on.”

LESSON #7: Change up your customer discovery to get the customer to convince you — not the other way around

As Seshan noted, while these questions apply to building any product — flagship or freshly conceived — new bets in particular need a strong answer to question number nine: How quickly do we start learning if our solutions are the right ones? 

Avoiding the happy ears problem is especially important here. “Something that a really great user researcher once told me is go to the meeting expecting the user to sell you on the product, rather than you selling them,” says Seshan. 

“In fact, you can even take the approach of almost not even owning the product, like, ‘Hey, this is the thing my buddy designed. I don't think it really works. You tell me what you think.’ You want to let them feel that they have room to say that this thing is useless and it's not right for them.”

Your default skepticism should be so high that the user is actually trying to convince you that this product is necessary.

LESSON #8: Hire for potential diamonds in the rough

In the jump from single to multi-product, Seshan doesn’t sugarcoat it —– this isn’t for everyone. “There are certainly some people who are suited for this type of thing and some who really aren't,” she says. “For new product bets, I strongly index toward hiring people for potential, not necessarily for experience. The hungry and high potential person who's dedicated to growing quickly, can build more value for the business than a status-y or experienced person who is less high potential,” says Seshan.

“The hard part here is trying to understand, of those early high potential candidates, who is great, given the paucity of detail in their background.” Seshan relies on the following specific criteria to help her find the diamonds in the rough: 

• Hunger: “Do they go above and beyond to show their interest? Do they message you repeatedly? Do they do something special to set themselves apart? I had a candidate who made me a YouTube video of why they want to work at Watershed, which sounds random, but these signals actually matter,” says Seshan. “If they’re showing they're hungry now, they'll be hungry on the job.” Look for how they’ve shown hunger in past experiences — perhaps from getting their past job in an unusual way, making opportunity materialize from nothing, or simply starting something of their own.
• High horsepower: “If they don't show high horsepower in some way, then it's an immediate no,” says Seshan. “Do they have a great side project? Do they write very excellent blog posts or documents or articles that show incisive analytical chops?”
• Wins above replacement: Another sports metaphor, but in short, hirers should ask: “Does this person do better than the other person at their same stat level because of some ineffable quality that they bring to the table? Separating their actions from those of their team or the circumstance — would the end result of the thing they did have been significantly worse without their involvement?”
• Drag things across the finish line: “Most smart people are actually terrible at having the drive or follow through to take the thing over the finish line. I remember back at Stripe, we were interviewing a candidate who came from Bain, and often they just want to focus on strategy. But this guy had implemented a call center project and stayed on the project three months longer, visiting the call center and taking calls with them just to see how it went.”

Of course, it’s much easier to probe for these traits with a set of interview questions. Seshan shares her favorites below:

• Tell me about something you learned recently. Did they learn about something complex? Can they explain it really well? Do they show understanding of detail?
• If your life was a book, give me the chapter titles from your birth till now. "When you get the full story, dive into each 'chapter' and hunt for their real stories."
• What project are you most proud of? “It's very telling to hear the type of story that they tell. The types of things that they're most proud of will almost always be things that are reflective of their strengths. If they don't give you a story that requires a lot of team coordination, you explicitly ask for that. Ask for the thing that has the most people or constituents involved to gauge whether they're a driver or a passenger.”

For even more on this topic of finding diamonds in the rough, Seshan wrote more on this topic in her newsletter recently.

LESSON #9: Pull out a different yardstick to measure the success of new bets

When it comes to new product ideas not panning out, one common failure mode Seshan flags is judging the net-new bet by the same yardstick that the rest of the company is judged on.

“And that is not just an executive decision, it cascades all the way down throughout the organization. The sales manager who is thinking about letting a seller go — will they allow for a seller to have a slightly alleviated quota to make a new product happen? The marketer who is stack ranking their work might let the new product fall to the bottom because it’s not going to have as much impact as the core product. Those decisions happen throughout the organization all the time.”

There is an important cultural motion that has to come from the top. Leaders need to say, “We are taking that new bet because we have to. Those actions are not going to be as efficient as betting on the core product, but if we don't do it, we'll never have a successful business.”

There’s heaps of advice out there on how to prepare for interviewing a candidate — tips for structuring the process, thoughts on the right set of questions to ask, and advice on distilling down the feedback across the hiring panel. It is an undoubtedly essential process to get right.

But, oddly, when it comes time to pick up the phone to call up references, far too many hiring managers treat this as a check-the-box activity, farming the process out to their recruiting partner — or perhaps even skipping over it entirely when they’re in a rush. 

There are plenty of well-reasoned theories for why folks take a haphazard approach here. Reference checks are the very last step in most interview loops, likely after rounds of time-sucking interviews, before the rush of making an offer. After a painstaking hiring process, sorting through dozens (or even hundreds) of options, there’s a candidate who the hiring panel is excited about. So folks go into the reference check looking to just confirm a decision they’ve already mostly made — after all, a negative reference could derail the entire process, and send it back to square one. Somewhat subconsciously, hiring managers ask soft-balled questions of the reference, who delivers the perfunctory, expected answers, and the cycle repeats until the offer is made.

When was the last time you heard something on a reference call that stopped you in your tracks or truly changed your mind?

Alternatively, even hiring managers who go into the reference phase with their minds not fully made up may still find that the process leaves much to be desired. These references were probably hand-picked by the candidate, and aren’t likely to be fully candid while parroting back all the strengths the candidate already told you about at length during the interview process. The hiring manager learns very little that’s new, and the whole reference process feels like wasted time.

After a few hiring cycles where reference calls play out this way, it’s not surprising that hiring managers start to write them off. But it’s an enormous mistake.

When approached with craft and care, reference calls can be a massively influential piece of the hiring decision. After all, you’ve spent — at maximum — a couple of hours with the candidate (along with perhaps reviewing some work samples or a practical exercise). Here’s your chance to speak to folks who have spent months, or even years, working closely with the candidate every single day. They’ve seen them at their absolute best — and possibly at their worst, too. 

To help add more rigor to references, we put out a call to startup leaders and operators in our community for their favorite questions to ask during reference calls, assembling our favorites into a comprehensive guide for hiring managers. 

Across the board, the experienced leaders we’ve spoken to agree that reference checks are a massively underrated component of the hiring process. It’s an essential tool in a leader’s tool belt — when approached the right way. The questions that follow skip the softballs and dig beneath the surface to uncover a more holistic picture of the candidate you’re considering hiring.

Looking to quickly access all the questions (plus some extra bonus questions)? We’ve assembled them into a handy guide for your next reference call Download the PDF below.

It’s a theme that’s also cropped up again and again on our In Depth podcast, and we’ve included advice from folks we’ve interviewed like former Stripe COO Claire Hughes Johnson, Lattice founder Jack Altman, and Thumbtack co-founder and CEO Marco Zappacosta. 

For example, Zappacosta has a well-honed playbook for hiring executive candidates, which involves talking to not two or three references but 10 to 20 people that he draws from various stages of the leader’s career, aiming to spend as much time on interviews as he does with references. (So if he’s spent 15 hours with a candidate, he’ll spend the same amount of time backchanneling.)

His number one piece of advice? Don’t try to boil the ocean here. “Get really clear with yourself about what you’re trying to understand. By having a narrow focus about the experience or skills that you want this leader to have, you can structure your reference call to ask about those questions directly,” says Zappacosta. 

There’s nothing worse than asking, “What did you think about this candidate?” or “Were they any good?” Of course, a reference by and large is going to say yes. They know and like the candidate more than they know and like you.

“Interestingly, over time, I have less conviction in the ability of an interview process to assess talent,” says Zappacosta. “Interviews or practical tests are often imperfect, they’re contrived, and they’re stressful in a particular way that regular work is not stressful. It’s an attempt at auditing someone’s fullness in a small number of hours — and that’s imprecise. So I put more weight on references as a way of auditing technical talent. When in doubt, when we feel a little hesitant, but the references say that this person was really strong in that particular skill, I trust the reference.” 

But your ability to trust that reference hinges on putting in the detective legwork that will help you build that more holistic picture of a candidate. And as with most things in life, the follow-up is everything here. Many of these questions have a set of detailed secondary queries, helping you to drill down even further and uncover what’s not being said. With that framing in mind, let’s dive in. 

QUESTIONS FOR ASSESSING HOW THEY STACK UP

1. How does this person compare to the best you’ve ever seen in the role? 

While this question is asking about the candidate’s chops, it’s also laying the groundwork for how much stock to take in the reference, too. “I first want to get a sense if the reference is a reliable judge by asking how they've worked both with this individual, as well as others in similar roles. If they've only worked with one Head of RevOps, then asking them to compare to others won't yield great data,” says Sean Twersky, Head of Business Operations at EvenUp. 

Similarly, Stacy Tumarkin, CFO at Kubecost, asks: How many people have you worked with in [candidate’s] role/level? How would you rank [candidate] among their peers?

And Nadia Singer, Chief People Officer at Figma, prefers this variation: What is something that [candidate] is better at than anyone else you've worked with in this role? 

2. On a scale of 1 - 100, how would you rank this person? 

Asking references to rate a candidate on a scale of 1-10 is a bit more common, but Twersky makes the case for a wider scale. “I’ve found 1-100 more insightful as you'll usually get a low 90's response, allowing you to follow up with ‘Ok, so why not rate 100?’”

While he’s looking for a high quantitative ranking, Twersky is also trying to get a feel for whether the reference is jumping out of their seat to tell him about the candidate. “Are they cutting me off to tell me how great someone is? I was doing a reference call for a Director of Finance and the reference interrupted me and said, ‘Look, I see where you're going. Let me be straight, [candidate] is the best strategic finance person I have ever worked with. She doesn't build the prettiest models but your team will love her and she'll be a truly value-add thought partner to you. Stop wasting your time and hire her.’ And he was right — she was one of the best hires I ever made.”

3. On a scale of 1-10 (10 being the highest), how do you rate XYZ on [specific trait or ability]?

Jason Yoong (former Head of Program at Amazon) sticks with the 1-10 scale — but deploys it in a very particular way. “I believe the 1-10 rating scale question is effective when used with two intentional follow-ups.”

What is the reason you did not rate XYZ (insert a number that is 1-2 points higher)? “This allows you to dive deep into the why as people share interesting reasons or past experiences, along with areas of improvement.” 

What is the reason you did not rate XYZ (insert a number that is 1-2 points lower)? “This gets to the candidate’s superpower.”

4. Can you tell me about a project that would have failed without [candidate]? 

“This question gives me more insight into the candidate’s perceived strengths as well as how much (or how little) initiative they take,” says Auzita Irani, Research Manager at Airbnb.

Along similar lines, to get past the surface level on a reference call, Vishal Kapoor (Senior Director of Product Management at Shipt) suggests: What is your most memorable experience working with this candidate?

5. What haven’t I asked that, if you were me, you would want to know about this person? 

While this might seem like a natural question to end the call with, Marco Zappacosta actually recommends asking it towards the middle of the conversation in order to unlock any unexpected rabbit holes. “This question gives references the free license to say what they’ve wanted to share,” he says. 

QUESTIONS FOR PROBING GROWTH MINDSET

6. Would you rehire this person for almost any role?

Loom’s COO Anique Drumright talked at length about her approach to reference checks on the In Depth podcast and shared that this is one of her favorite questions to lean on. “Because there are certain people that you truly would rehire in just about any capacity. But often in response to this question, you’ll hear many caveats: ‘Well, it would really depend on what the role is — it’d have to be this specific thing.’ That’s an indicator to me that this candidate is not as flexible or as much as a generalist that I need right now,” explained Drumright. 

Across the board, with her full slate of questions, Drumright underlines that she’s acutely listening for a particular flavor of zest and gusto. 

I'm really listening for how enthusiastic or passionate they are when they talk about the candidate. There are some people on my team that I can’t wait for the day I get to give a reference for and talk about how amazing they are for 30 minutes.

As Upstart founder and CEO Dave Girouard told us, with this question (and just about every one on this list), it’s critical to be blunt with your follow-up. 

"Most people don't want to lie. I know when I've given references for people who I had mixed opinions about, I always told myself, 'I'm not going to lie, but if they don't ask the right questions, that's their problem,'" says Girouard. To get around that tendency when you're the one dialing up references, sometimes you have to be blunter. "One of my favorites is, 'Would you hire this person without question again?' If the person says, 'Yes, no matter what, I would hire this person again,' I would say, 'Great. That's a good answer. Why haven't you?' If they answer with some reservations, then you can ask, 'What are the circumstances where you would, and what are the ones where you wouldn't?"

7. What was an experience where you saw the candidate grow?

Here, Vishal Kapoor is looking for precise examples of how the candidate evolved, and he always follows up with: What might still be the candidate's growth areas?

8. Can you share an experience where [candidate] really blew your mind? 

Subscript’s founder and CEO Sidharth Kakkar likes this twist on the question. “You get to see if they can come up with anything, and you can evaluate if it is really truly impressive. The best candidates spike very high in some things, and you can get confirmation that this person really is spectacular at something.”

9. [Candidate] said one of the things they struggled with when they were at the company was [weakness]. Do you recall cases where that got them into trouble? 

Asking about weaknesses in a reference call can be tricky — after all, the reference is likely rooting for the candidate and trying to present them in the most positive light. So Subscript’s Sidharth Kakkar starts the question off by specifically mentioning something that came directly from the candidate themself. “This gives the referencer permission to speak about a weakness — since the candidate already brought it up — and then you can figure out exactly how problematic that weakness was.”

Another approach here, from Marco Zappacosta, is to flag feedback from other references, and ask folks to react to it, giving them permission to be honest about any red flags: “I’ve talked to three other members of the executive team at this company and they all called out this issue. What’s your read on that?”

10. Do you have any examples of times when the candidate demonstrated grit? Not giving up?

Jad Esber (co-founder and CEO of koodos labs) recommends this question to dig beyond the bullet points on a candidate’s resume. They might be a performance marketing wizard, but what are moments or stories that might not be adequately captured on a resume? 

QUESTIONS ABOUT ROLE FIT

11. Explain the role at length and what success looks like in the first year. Do you think that [candidate] will thrive in that position? 

Looking back on some of the mis-hires she’s made over the years — and how she could have approached the reference call differently — former Stripe COO-turned-advisor Claire Hughes Johnson flags a common bug: skipping over some essential context setting.

Titles don’t tell you everything. I’ve made the mistake of going into a reference call and assuming that a Head of Sales role is understandable enough and I don’t need to describe my version of it to the reference.

As she told us on the In Depth podcast: “I should have given the current context of what success looks like and what I believe to be the capabilities that the candidate needs to spike. Give the reference enough flavor and ask them to react. Where I’ve failed in the past is assuming they would intuitively understand what was needed in the role,” Hughes Johnson says.

12. Tell me about a time when you saw this leader build a new team. They said they did it at the company. Can you tell me what you observed? 

Another common mistake that Thumbtack CEO Marco Zappacosta flags for folks is being too wide-reaching in your reference calls. Instead of trying to learn everything possible about the candidate, choose a much narrower scope. 

You can swap the example of building a new team that Zappacosta provides for any tangible skill or achievement that’s most important in your hiring search — the point here is to get precise. “When you ask somebody a specific question, not just general impressions, people typically let their guard down and share more details. Listen super carefully to the language people use, because it's sort of a coded conversation.”

13. If you were to design an ideal role for this person, what would it be?

First Round Partner Brett Berson likes to give the reference plenty of space to color outside of the lines with this question. 

Stacy Tumarkin’s approach to this question gives the reference ample opportunity to talk up the candidate’s superpowers, while also nudging them to point to where there might be opportunities for growth: In which kinds of projects or work is [candidate] most effective? Which situations are more challenging?

14. What was something unique about this candidate's team versus other teams?

Vishal Kapoor suggests asking this question for any candidates who are applying for people manager roles. 

QUESTIONS ABOUT REAL-LIFE WORK SCENARIOS

15. Can you tell me about a time that the candidate missed a deadline and how they communicated that to you and the broader team?

"I assume that a reference will be largely positive, so I like to use the time during a reference call to learn about how the candidate handled situations that did not go so great. It helps me glean insights into how working with the candidate would be,” says Kanan Kapadia, co-founder of the Abstract Group. 

16. Can you tell me about a time when you had to provide critical feedback to [candidate]? How did they receive it and what actionable changes did you see after the feedback was delivered?

Another suggestion from Kapadia, being able to take feedback well is essential for any startup employee up and down the ladder.

17. How does this person deal with differences in opinion?

Connor Fitzgerald, Director of Business Development at Coinstar, makes sure to touch on this question because, as he tells it, the majority of stress in the office can often be boiled down to well-meaning folks disagreeing. Make sure to probe the reference to provide real-world examples here, rather than just being satisfied with a hand-wavy answer. 

18. Can you share someone who maybe doesn’t necessarily get along with [candidate] as well as you do? Why do you think they don’t mesh well?

Not everyone will be universally liked across the company — and that’s not even necessarily a bad thing. Brett Berson leans on this question to dive deeper into where the candidate might experience points of friction if they were to come on board. 

19. What was [candidate’s] reputation within the organization or department? Among customers?

Here, Stacy Tumarkin is looking to expand a bit beyond the immediate team — how does the candidate wield influence across the org? How do they approach building and maintaining cross-functional relationships? 

QUESTIONS FOR SETTING UP THE MANAGER / DIRECT REPORT RELATIONSHIP

20. What "special treatment" helps [candidate] do their best work?

This question from Brie Wolfson (a former marketing leader at Stripe and Figma) harkens back to what was once one of her least favorite bits of leadership advice that she came around to eventually.

I had a soccer coach in college who would always say, “There's nothing more unfair than to treat everyone the same.” It drove me nuts then, but now that I'm a manager, I understand what she meant.

21. How well do you think [candidate] will do with my management style?

“Be aware that most references are cautious to say anything that will cause the individual to lose their offer. So use this opportunity to have an honest discussion about the work the candidate is about to embark on,” says Richard Cho, Head of People at Alchemy. “Be specific about your environment and the values and characteristics that allow for anyone to succeed.” He shares a few examples of how folks might frame this question: 

• “I'm a very hands-off manager, to the point of benign negligence...I need someone to 'manage me' as I need to juggle priorities daily. How do you think the candidate will do with that management style?”
• “Our environment rewards action-oriented people. How comfortable is [candidate] with shipping deliverables quickly and iterating on the work over time?”
• “How does this person do with multiple urgent deadlines that converge and will require the individual to self-prioritize?”

Don't be afraid of painting such an honest picture to the reference that you are worried about the candidate declining the offer — it's a blessing in disguise.

22. What causes the candidate stress or friction? 

“My reference questions are all variations of the first 1:1 questions I have with my direct reports. My goal for reference calls is to understand how to be the best manager and leader to my new hire, rather than find reasons to not work with them,” says Danielle Leong, VP of Engineering at FireHydrant.  

“By asking about stress, it places the reference in a more contemplative mood, rather than a selling mode. I find I get very honest questions about what the candidate values, how they react to stressful situations, and what can be done to mitigate it.” 

23. How do you think I can best support this person to make sure they thrive here?

"Especially if this is someone who will report to me, I always like to ask this question. It's a nice way to frame up things that their manager might have seen them struggle with in the past — and to just get some straight-up pointers from another manager. This question has been huge for building trust with new reports, as well,” says Sara Caldwell, VP of Customer Experience at Dovetail.

24. How did you build trust with this person?

“Not only is it a positive signal about me to the reference (who most certainly will tell the candidate about how well this call went), it’s also a genuine question that I want to know more about. What was their past management experience like? What sort of potential landmines are in their past? How can I best navigate these?” says Danielle Leong. “Since we're an early-stage startup and we all work so closely together, these are important pieces of information I'll need to understand how best to work together and mitigate any issues quickly.”

25. If you heard in three months that this person was no longer working at our company, why do you think they would be gone?

“I always ask this question because it causes people to stop and think, and it often provides information that didn't come up in any of the other questions I ask. The answers vary — sometimes the references focus on what might drive a person to quit and others talk about what sort of situation would make someone fail to do the job well. But every answer I've gotten has helped us better prepare to have the candidate join our team," says Margie Mathewson, SVP of Business Operations at Ossium Health.

WRAPPING UP: PUT IN THE WORK

With a couple of reference calls under your belt — all ringing endorsements of your top candidate most likely — it might be tempting to put the phone down and start preparing the offer letter. But this isn’t the time to get complacent — particularly if you’re hiring for a high-impact leadership role. As Jack Altman told us when he joined the In Depth podcast, he often ends his reference calls by trying to get more references — with a specific mandate. 

“The questions I ask are, ‘If I want to be convinced that this is the right person for this job, who else do you think I should talk to? And who should I go talk to that’s going to tell me that this might be a mistake?” says Altman. 

Don't be scared to keep asking for more names. Any one reference is a little bit of a tenuous signal, but you start to get six, seven, eight people who know this person and have worked with this person for years, you can get a really strong hiring signal.

Often, hiring managers are hesitant to keep asking for more and don’t want to come across like they’re digging for dirt. But Marco Zappacosta backs up Altman’s approach. “Every executive who has had a long, storied career will have something that they wish they could change. I'm not going to ding somebody for those things. But I want to understand the range of the spectrum from the best to the worst,” he says.

And to take things even further with executive candidates, he’s added on an extra layer by presenting the results of the references on a final call with the candidate. (To put candidates more at ease — and make the evaluation bi-directional — Zappacosta has shared a copy of his own recent 360-degree review results in the past.) 

“I’ll tell them that I spoke with people across different companies and domains, and we go through each theme for areas of excellence and improvement. Take note that you’ll get a wider band of feedback here than what was discussed in any interview,” says Zappacosta. “My question for nearly each section is: ‘Why do you think I heard that?’ I’m listening as much for the answer as I am for how the candidate responds. Are they defensive and try to explain away the observation? Or do they say something like, ‘This is what I've been working on for a long time. I'm not a natural public speaker. And, as my role has grown, that has become more of a necessity. I’m more comfortable in small groups, but I’m taking a more active role in All Hands and sign up for a few conferences a year.’”

Growing up in a suburb of Buenos Aires in the 90s, Guillermo Rauch didn’t know many people with computers. So at seven years old, when he booted up Windows 95 on the PC his father brought home, Rauch was mesmerized by this new technology.

“My dad challenged my brother and me to explore what we could do with it,” he recalls. “Could we install software? Could we hack it? He had this very experimental mindset about it.”

Up for the challenge, Rauch began teaching himself to code. It was the early days of the internet, so there wasn’t much information online, and it wasn’t usually in Spanish. So, undeterred, Rauch taught himself English, too. His first goal was to replace Windows with Linux, a difficult task that led him to an enthusiastic group of strangers online who shared their programming expertise for free: the open-source community. 

Through his early teens, Rauch had an insatiable appetite to learn everything he could about Linux, JavaScript and web development and built up his reputation as an open-source contributor and frontend developer.

“I would create these demos that would make it to the front page of Digg and Reddit. I was becoming a five-minute internet celebrity every time I would create a really cool demo using these frontend technologies,” he says. “The thing that I was most passionate about, which was making UIs faster, more dynamic, more real time, also started gaining more prominence.” 

When he was just 16, Rauch became a core developer for the open-source project MooTools, and later, Facebook came calling with interest in hiring the young phenom. That’s when he realized that this hobby could become a career. He dropped out of high school and eventually moved to San Francisco to start his first full-time job as a software engineer — at just 18 years old. “Open source really was my path out of Argentina in the end,” says Rauch. 

He didn’t know it at the time, but open source was also his path to a billion-dollar business. His company, Vercel — the frontend cloud service behind open-source development framework Next.js — was recently valued at $2.5 billion. If you’ve ever visited the websites of eBay, Zapier or The Washington Post, you’ve seen Vercel in action. As for Next.js, more than 850,000 developers use it to build websites with billions of global users, like ChatGPT, TikTok and Notion.

While achieving product-market fit in any form is cause for celebration, Rauch has managed to reach its highest level, what we at First Round call “extreme product-market fit.” This means his product has earned profound, widespread customer love and demand and is delivered through a scalable, profitable go-to-market motion. 

In this exclusive interview, we deep-dive into Rauch’s process for building such beloved developer tools, his fresh approach to monetizing an open-source project, the early PMF signals he detected and what he would go about differently if he could do it all over again.

EARLY INSPIRATION FOR VERCEL

When Rauch packed his bags and moved from Buenos Aires to San Francisco in 2006, it was a pivotal year for cloud computing. Amazon Web Services had just launched its first product to the masses, and Rauch was among its first users. With AWS, developers worldwide were now freed from having to manage their own servers and hardware resources, and could build and deploy web applications more quickly and easily than ever before — or so, that’s what was promised.

“Computers were now in the cloud. It was magic,” Rauch recalls. “Hardware became software. It’s so abstract, the idea that there are robots moving hardware around in racks somewhere, and I just don't see it. So we had that foundation of magic, in theory. But then, when you actually used it, doing anything with the cloud was so freaking hard.”

Even as a technical wizard, the cloud’s flaws frustrated Rauch — but he tucked away this little kernel of an idea for a few years while he worked as a frontend engineer. His foray into entrepreneurship, and the foundation for what would later become Vercel, officially began in 2010 with his first startup, Cloudup.

“Cloudup was an early inspiration for Vercel in many ways,” he says, “because one of the killer features was you would get this application that sat on your menu bar, and you could drag and drop any file or even a folder of files, and it would immediately give you a hyperlink. It was the easiest way to share anything on the internet and collaborate with others. And you could actually drag and drop a folder of files, and if those files were HTML, you would get really high-performance static hosting.”

While Cloudup was still in private beta, Rauch showed it to the founder of WordPress, whom he’d connected with thanks to his involvement in the open source community. 

“When I showed him Cloudup, he thought it made a ton of sense in the context of WordPress because they’d been investing really heavily in modernizing the frontend layer. They were really interested in the real-time technologies for collaboration so that you could go to WordPress and edit posts, which later became the foundation of their block-based editor for WordPress 5.0.”

WordPress’ parent company, Automattic, actually snapped up Rauch’s company before Cloudup even launched to the public.

A familiar problem rears its ugly head

After the acquisition was finalized, Rauch began working at WordPress. But in his new role, Rauch bumped up against that thorny problem once again: Why was the cloud so difficult for developers to use?

“At WordPress, they had invested millions and millions of dollars into becoming proficient at hosting one application: Wordpress.com. But adding any incremental new app, product or feature was extremely tedious,” says Rauch. When everything is in one code base (a “monolith”), the database and the code are so intricately tied that it constrains what developers can do.

It was hard to get that freedom as a developer. I wanted to try new frameworks, new frontend solutions, but I was constrained within the confines of a monolithic solution.

“This wasn’t solely a WordPress problem — at the time, the entire industry was primarily these monolithic architectures,” says Rauch. “But the world was slowly starting to move in the direction of microservices and composability, breaking down these monolithic ways of building. And the promise of doing that was that developers would get a lot of flexibility. That's what the cloud promised me — that I was going to be able to move really fast.”

The gears were turning in Rauch’s head. In November 2014, he outlined his seven principles for a better user experience for web applications in a blog post that would later become the blueprint for Next.js and Vercel.

“At the time, I didn't have a framework yet. I didn't have the technology to turn these principles into action, but that blog post kind of became the master plan for what later became Next.js,” he explains. “I had reverse-engineered how Google Search, Facebook and Amazon were built, and I realized that whatever framework I built in the future should have no compromises. It should be able to build anything from a small website to something that scales. I wanted to be able to put it in the hands of someone who's building the next Amazon.com or the next Google.com. Setting that really high bar gave me that direction to be able to build.”

Everything around me had failed to fulfill the cloud’s promise of making development faster. So I decided I was going to make deploying software completely instantaneous and give that power back to the developer.

In November 2015, Rauch left WordPress to build his solution, which he called ZEIT (later, the name would become Vercel). As soon as he began the task of building a website for his new company, he encountered friction that further solidified his belief that the cloud needed a major overhaul. Sure, there were SaaS solutions for launching simple websites (like Squarespace), but Rauch wanted to build a production-grade stack that had the complexity of AWS and a marketing website that was on par with any top-tier enterprise marketing website. 

“Just that first three or four weeks of trying to put up a website confirmed all of my previous hypotheses of, ‘Holy crap, how have we made the cloud so hard to use? How have we made the simple act of putting up a new idea, a new website, so difficult?” he recalls.

If Rauch, a solo developer, was struggling to build a highly dynamic website for his company of one, imagine the next 100,000 businesses that would struggle with their digital transformations because the technology they were building with was lagging behind. His solution, then, would be a deployment platform specifically for the frontend (his specialty and the part that users actually see) that would make it easier, faster and more reliable for developers to get their projects out into the world.

BUILDING THE PROTOTYPE

While he was still in the process of finding two co-founding engineers, Rauch tasked himself with an ambitious goal: He would put out a prototype of his deployment platform in just three months. 

“Creating infrastructure like that in three months is very, very difficult, but I wanted to create a deadline for myself to start getting feedback. In the process of building, we realized that a deployment platform needs a dynamic web application to be able to do things like orchestrate and see logs. There was a lot needed for a platform like that.”

React, the JavaScript library with which he was building, was great for developing an app, but when it came time to get the finished work in front of end users, React was frustratingly slow. Rauch wanted a framework to expedite the process.

“I describe it like this: React was a great engine, but I needed a car to get from point A to point B. That’s why I started working on this framework, Next.js, which at the time was internal. We started kicking the tires on this tool, at the time we called it N4, and every day, we're like, ‘Hmm, this is working really well, we're moving really fast, it's giving us the results that we wanted.’”

Six months later, N4 was too good to keep to themselves. Rauch released it as an open-source project under the name Next.js in October 2016. It was an instant hit with developers.

“To outsiders, it seemed like an overnight success because Next.js had a lot of attention and adoption from basically day one. But they hadn't seen all this development that went into it before. They hadn't seen all these internal battles and pressure testing. I had been thinking about the principles that the framework would live up to since two years prior, or even more. So the overnight success story is a bit of a myth.”

When your product solves a huge pain, you should see pretty fast growth almost right out of the gate. It's obviously hard to get the product ready, but at the point you release it to customers, you should see rapid growth.

MONETIZING AN OPEN-SOURCE PROJECT

You could call it a happy accident: Rauch had initially set out to build a platform to help engineers deploy their projects, but along the way, built a React framework that became an instant open-source sensation. 

But coding a successful open-source project and building a successful business are often at odds with each other in one key aspect: money. Most open-source software is available for free and doesn’t aim to ever turn a profit. The few that do, face limited options.

“When you try to go from open source to business, there's not a ton of creativity there. You either go open core, which is where you basically limit the free features, or you use some kind of license that allows you to give features but constrains how they're used and deployed.”

Having come up in the open source community, this rankled Rauch, and he didn’t want to restrict his Next.js customers. So, he took a fresh approach.

You have to align the value creation of open source with the value creation of the business that supports that open source project.

“In our case, we developed an infrastructure business with Vercel at a global scale that aims not to just host the products, but entirely outsource teams’ worth of responsibility for the companies that use our system,” he says.

Here’s how it works: To this day, anyone can use the entirety of the Next.js framework for free. If they want their projects hosted on a platform specifically built for Next.js, one that enhances what they’re building, they pay Vercel for that upgrade. And because Next.js remains open source, if the customer ever decides they want to take their workload off of Vercel and self-host it, they’re free to do so. They’re not locked into a single vendor.

“So it's a very simple equation on the infrastructure side for a company to say: ‘Do I stand up a team of like 20 software engineers? Or do I hand this off to Vercel so they take care of it?’ I had a customer in Japan recently give me a presentation of how many engineering resources they were able to redirect from platform engineering to product engineering and data science because Vercel freed up the infrastructure resources of that company to be able to create customer value and customer insights instead,” Rauch says.

“So that's the other type of business that you can build with open source. As the company gets better at evolving its own infrastructure, it's very hard to compete with.” 

He points to the example of MongoDB, an open-source project turned business that generates $1.5 billion in annual revenue. It makes money by charging for hosting on its fully-managed MongoDB Atlas database as well as for support and consulting services.

“If I use MongoDB, I’ll be the first to tell my team, ‘Let's give Mongo to the experts of hosting Mongo. Let's give it to the folks that have been hardening this system at scale.’ But it gives me confidence to know that I'm betting on an open platform, so if I decide not to do so, I have the freedom to take the workload with me. That’s why open source is, in my opinion, the best option. Because if there's a company supporting it, I can automate a lot of my work away. And if, for whatever reason, I need to do it on premise, I also have that option.”

If I were to do it over again, I would do it the same way: using open source. And I would continue to invest in making the product as free and available as possible.

Rauch managed to create a brilliant synergy between his products: The widespread popularity of Next.js, which remains open source, set up Vercel to become a revenue-generating complementary product because Next.js users naturally gravitate toward the platform built for that framework. And in turn, Vercel’s revenue funds the upkeep of Next.js. It’s a win-win for both the software and its customers.

SIGNALS OF ‘EXTREME PRODUCT-MARKET FIT’

Identifying the precise moment you’ve found product-market fit can be tricky for any founder. For Rauch, it was especially so because of his existing popularity in the open-source world.

“At the time that I released Next.js, I already had quite a bit of a following in the developer community because of my work on MooTools, Socket.IO and Mongoose, so I could easily get folks to at least look at what I was going to ship.”

So the fact that other developers were eager to get their hands on his latest software wasn’t enough for Rauch to believe he’d nailed product-market fit. Were people clamoring for Next.js because of the solution, or because of his own cache? Instead, the strongest indicator that he’d built a product that solved a real problem was that he had some competitors. Big ones.

“Right after we released Next.js, someone from Redfin reached out saying they were building the same thing. And then a week later, someone from Trulia reached out saying they were building the same thing. These were not just folks doing little experiments. I had all these people running businesses at scale telling me that they were either building a version of this, about to assemble a team to start building a version of this or asking me to share ideas and best practices.”

One signal of product-market fit that I recommend you pay attention to: When something is really needed, you’ll find there are lots of very intelligent people at other organizations trying to build a version of it.

And despite all the customer love for what Rauch had built, that doesn’t mean it was without its critics.

“Not everyone in the developer community was jazzed about Next.js, and there were some competitive alternatives at the time that had a completely different philosophy,” says Rauch. “So it wasn't that we’d won right away. We had to navigate that market and the competition for quite a few years.” 

One aspect of Next.js that ruffled some feathers? It uses server-side rendering, going against the grain of the more popular client-side rendering. But thanks to his thorough market research, Rauch was confident he’d made the right call.

“Years ago, when I’d reverse-engineered Amazon and Google and Facebook, it was like, ‘Wait, these folks are not doing it that way. There must be a good reason for performance and scale and privacy and many other things.’ So it was interesting because, for a couple of years, we had these almost competing signals, with certain individual developers not liking it but larger organizations being super excited about it.”

4 LESSONS ON BUILDING SOFTWARE THAT CUSTOMERS ARE OBSESSED WITH

From Cloudup’s acquisition by Automattic to Vercel’s impressive customer list that includes Adobe, Loom and Meta, Rauch has clearly figured out the formula for building software that solves real problems. He unpacks the most poignant lessons he’s learned from his decade-long journey of entrepreneurship.

Instead of building more, become exceptionally good at less.

Rauch's first startup, Cloudup, actually began as a product for a particular industry vertical: as an edtech platform with a wide variety of products. But when Rauch noticed that teachers were using one specific feature, file sharing, to send lesson plans, he decided to distill the product offerings down to that most-loved feature and pivot the edtech startup to what became Cloudup. Rauch credits this move for helping him achieve a successful exit. Later, he applied this same crucial lesson to building Vercel.

“One of the catalysts for finding joint product-market fit for Next.js and Vercel was us simplifying the offering. In the beginning, the very first prototype of the deploying platform was focused on deploying absolutely everything. And then we realized, we're making the frontend-facing part of a website better. We were giving people the best React experience. So why were we trying to make everybody happy? Why don't we simplify the offering? After that, we decided to build the frontend cloud, whereas, in the beginning, we were trying to build the cloud.”

“The last thing an enterprise wants to hear is, “Oh, here's a thing that does everything and promises it can solve every single one of your problems.” Buyers are just so tuned out of that narrative.

Velocity matters more than speed.

“Move fast and break things” has come to represent the ethos of Silicon Valley startup culture, but Rauch cautions against pursuing speed for the sake of speed.

Focus on iteration velocity, rather than speed. Velocity is speed with direction — you know where you're headed. Or even if you don't know where you're headed, you're seeking direction. That doesn't mean you're just writing code 20 hours a day and churning out features left and right.

Rauch is admittedly speed-obsessed, so this was a particularly important tool for his toolbelt.

“The ways that this has shown up in my career is that sometimes the solution was to build less and focus more. Sometimes, it was to really pay attention to what customers were trying to tell us. For someone who loves to move fast more than anything else, I think that was the right complement that I needed to add to my framework to be truly successful in a durable fashion. In the early days, finding that direction is the most important thing you could be doing.”

Don’t underestimate the power of integrations.

“In the early days, I underestimated just how much value can be accrued in having exceptionally good integrations,” says Rauch. “That's a trap that founders can fall into: Instead of integrating, they try to boil the entire ocean.”

“It's much better to say, ‘We do not solve that set of problems, but we integrate into solutions that you’ve already bought.’ Your strength can be in what you don't build, and instead, in what you integrate with. And that's especially true if you want to reverse engineer Vercel’s product-market fit,” Rauch says.

“That was a key unlock for our growth. Instead of saying, ‘Oh, by the way, we also have a Git hosting service. Please use ours.’ We can say, ‘Vercel has Git integrations so you can deploy your GitHub or GitLab projects with us.”

When your product is new, make the messaging relatable — not category-defining.

In the present day, Vercel is known as the category-defining frontend cloud. But that wasn’t the framing for the product in the early days, and Rauch cautions founders against trying to launch with brand-new messaging when storming onto the market. 

In the early days, your priority should be to make your product relatable. If you’ve got a small team, only three landing pages and you're kicking the tires on an earlier version of the product, giving yourself some very lofty tagline ends up playing against you because no one knows what you do yet, so they don’t understand.

“Today, I think Vercel has earned the right to try to define a category and adopt that lofty position as ‘frontend cloud,’ but in the early days, we had to be super specific and humble in our language. The team and I were laughing because we looked at earlier versions of the Vercel website the other day, and we're a little bit embarrassed because we had oversimplified the product’s tagline in the hero image. I can't remember exactly what it was, but imagine saying, like, ‘Faster websites, made easier.’ It was a very simplistic thing, but it was relatable for where we were, so it worked at the time.”

THE PATH FORWARD

Today, Vercel is a Series D startup with a total funding of $313 million. As the company has grown, it’s expanded to offerings that fall under two product categories: managed infrastructure and developer experience (DX) platform. And in 2023, Vercel made big bets on artificial intelligence with the release of v0.

“With v0, we're pioneering this concept we call ‘generative UI.’ You type the text prompt in plain English, and we give you the real-world React and Tailwind code that does exactly what you described. AI is the next frontier for how we’ll improve the developer experience, make developers more productive and help companies iterate faster. ”

For aspiring entrepreneurs, Rauch sees a huge opportunity to leverage AI and the move toward frontend services to take a bite out of the market. And as we’ve covered time and time again in this series, product-market fit is a moving target, and Rauch looks to take his PMF lessons to build and scale this new iteration.

“Too much is discussed in the context of ‘AI will replace A, B, and C.’ I think AI will act as an accelerator of human potential. As a programmer, a lot of my tasks are very tedious, very manual. AI takes those things off of my plate plus generates ideas for inspiration so that I can be more creative,” Rauch says.

“Obviously, as a platform, we're biased because we're seeing so much excitement on building AI products. But even as an entrepreneur, I get really giddy about all of these new products that will be brought to market because of AI, if you're willing to go beyond focusing on how products were built in the past.” 

Branding can be brushed off as an unnecessary upfront cost, a problem for your future founder self that’s easy to de-prioritize when you’re leading a cash-strapped startup. But investing in thoughtful branding from day one pays dividends — especially in the increasingly competitive (and expensive) battle to acquire customers.

Just ask the founders of Studs, Anna Harman and Lisa Bubbers, who stormed onto the startup scene in 2019 to transform the tired ear-piercing experience. Ear piercing was hardly a novel concept, but options were limited to tattoo parlors and mall kiosks. With a vision to meld a strong brand with operational rigor and re-package the experience of getting your ears pierced, this duo has since built a thriving business that’s expanded to 21 retail stores nationwide.

Today, the four-year-old startup is known for its colorful, Instagrammable storefronts and its wide array of mix-and-match earrings that it also sells online. Combining Harman’s background as an operational powerhouse with Bubbers’ marketing chops and sixth sense for stylish creative work, the pair have built a buzzy consumer brand that quickly became a Gen Z and millennial fave.

As co-founder and Chief Brand Officer, Bubbers has been the driving force behind this work, stewarding everything from the brand identity and strategy, to the store design and content marketing efforts — all the work it takes to bring a brand to life. From coverage in Vogue that billed the startup as “The Glossier of Piercing Studios,” to partnerships with everyone from celebrity gossip account Deux Moi to the Shake Shack burger chain, she’s made a lot of exciting moves, building a beloved, but surprisingly capital efficient, brand.

These two attributes often seem more like opposing magnets in the DTC and retail spaces. For a consumer startup that has made branding a key cornerstone of its strategy, it’s unusual that Studs spends less than 5% of its total budget on marketing. “Some founders spend $300K on a fancy agency for their brand identity, but I spent $50K working directly with designers. Our marketing launch budget was only $75K,” she says.

So while a retail piercing and e-commerce company may not seem like an obvious place for B2B SaaS startups to pull inspiration, as seed supporters who’ve been observing Studs’ journey from the very beginning, we think there’s plenty to learn from here regardless of your business model — particularly for the cash-conscious founder. “A lot of people are trying to figure out how to use experiential and retail as a marketing engine right now because direct-to-consumer costs for acquisition have skyrocketed and acquisition levers are limited,” says Bubbers. 

In this exclusive interview, she breaks down how branding should fit into your pre-launch efforts, shaping how you think about the going to market side of the product-market fit equation. Once you’re in market, her advice for growing, activating and retaining your audience is equally razor-sharp, including the nitty gritty of making your TikTok resonate, choosing the right influencers to partner with, and pulling off creative eventing. 

PRE-LAUNCH: HOW TO THINK ABOUT BRAND WHEN GOING TO MARKET

When it comes to building from 0-1, certain milestones are necessary (and obvious), like building the early version of the core product and acquiring your early users. But molding the company’s brand has no tried-and-true timeline to stick to — which leaves founders and early marketing hires unsure of when to kick off their brand building efforts in earnest.

“The level of importance you should place on brand and how much to invest at an early stage depends on how consumer-focused your business is and how folks engage with your product,” Bubbers says. 

“Our core offerings at Studs are ear piercings and earrings, which fall into a lifestyle category,” she says. “People get ear piercings and purchase earrings because they want to enhance their style and say something about their personality. It’s fun and aspirational. So for us, it was very clear that investing in a brand with the right customer experience, and content, would impact the business and our connection with our customer base early on.” 

But there are plenty of non-consumer businesses that also should consider investing in brand sooner rather than later, as Bubbers explains. At the very least, early branding exercises and validating product-market fit can go hand-in-hand, as they both require getting into the minds of your core customers.

For founders who are in the pre-launch phase of their journey, Bubbers presents some practical methods to gauge whether your company is truly ready for the spotlight, sharing a few lessons back from when she was still nailing down the studs behind her startup’s brand.

1. Test your brand hypotheses with a Minimum Viable Brand.

By now, every budding founder has surely heard about the power of building a Minimum Viable Product to launch as soon as possible and collect valuable early customer feedback. (Longtime Review readers may remember the alternatives we’ve shared here over the years, from Minimum Loveable Products, Jiaona Zhang’s tweaking of the same concept, or the Minimum Viable Test framework, an alternative approach coined by Maven founder Gagan Biyani.) 

But as Bubbers notes, these same principles can also be applied to your startup’s brand identity. “Before founding Studs, I was the sixth employee at interior design startup, Homepolish. When I first joined, the initial brand the founders had built looked a lot like Taskrabbit,” she says. “They focused more on getting the product out in the market to see if there was customer traction. Only then did I focus on giving the branding a fresh coat of paint to make it more polished — what you would think of when hiring an interior designer, rather than hiring a handyman.” 

But while it’s often a best practice to make speed a habit and move to quickly spin up an MVP, it’s equally important to recognize when your startup idea might not be a good candidate for this approach. As a company with its sights set on building brick-and-mortar stores, Studs was on the other side of that coin. 

“We couldn’t have a traditional minimum viable version of our brand, because our version of a launch was opening up a store,” Bubbers says. “As soon as you have a storefront on Prince Street in New York City, the brand is out there. There is no password-protecting your store out in the world. That was a big tell that we had to have a brand fully ready to go before launch.” 

To test out the core product experience, the Studs co-founders set up their own version of an MVP: a very unglamorous pop-up. “Before we opened a single store, we spent six months in a rented office with a piercer, bringing in our target customer from our network in New York to get pierced. It wasn't branded at all. All we were doing was talking to them and learning about the customer and what they wanted from this experience before we put our preferred brand out in the world.” 

2. Give your early branding and ICP some breathing room.

After confirming they had a real whitespace in the market to color in, one persona stuck out as a potential early adopter wedge. “I felt like if we could capture the cool 23-year-old living in Manhattan and Brooklyn and get them to be obsessed with the brand, it would give us a brand validity that would allow us to grow and become more mass,” says Bubbers. 

“As we’ve become national and have expanded to over 20 studios, the customer mix has really changed. The customer who’s getting pierced in Seattle is different from the one in Wisconsin which is different from the one in LA.”

The brand identity Bubbers architected purposefully allowed for that flexibility. Walk into any Studs store around the country, and each will feel like its own art gallery. “There’s neon colors, acrylic visual merchandising, and selfie mirrors,” Bubbers says. “It was created to be a destination for people, a cool place to go.” But what you won’t find in any Studs location are photo advertisements with models, one of the intentional ways Bubbers designed the spaces for inclusivity. 

“We don’t have lots of photos of a certain type of person where a potential customer could think ‘Well, if I’m not that person, then I don’t really need to be here,’” Bubbers says. “80% of women have their ears pierced, and that’s a growing percentage. So in the initial days of figuring out the brand strategy, we decided we couldn’t alienate anyone.”

In the beginning, targeted, really crisp branding is great, — but don’t make it purposefully so narrow that you can’t expand from there.

3. Leverage the “jobs-to-be-done” framework to fill in your branding elements.

In the long laundry list of items that go into unlocking extreme product-market fit, customer discovery gets top billing. For help here, Bubbers likes to turn to the classic “jobs-to-be-done” framework. 

The popular approach boils down to the belief that customers are not looking to buy a product, but rather seeking to accomplish a particular task. (For more here, we highly recommend diving into this lightweight JTBD framework for startups.) With that framing in mind, Bubbers offers up a checklist of questions founders can ask themselves before graduating into the brand work phase of their startup: 

• Is your product needed in the market? What’s the white space?
• Is there a customer profile out there that would “hire you” and pay for your product?
• How much would a customer pay for your product?
• What will your business model be?
• Who is your early adopter?

“Once you have an understanding of all these different pieces, then you know you’re ready to focus on building the foundational elements of your brand,” she says. For a pre-launch Studs, this looked like: 

• Brand Mission & Vision: Studs launched Studs in 2019 with the mission to reimagine ear piercing for today’s Gen Z and millennial customers.
• Competitors: “One of the reasons people get their ears pierced is to do a spontaneous fun activity. If you think of the jobs to be done framework, our competitor is anyone in the neighborhood that could give you a spontaneous fun activity after brunch, not just other ear piercers,” she says.
• Value Prop: “In our research we learned two key things for our target Gen Z & millennial customer. First, our customer really valued expert ear piercing with needles — not piercing guns — and they wanted a premium piercing experience at an accessible price,” says Bubbers. “And second, it seems obvious, but it’s harder than you might think to find a place that both pierces your ears and sells earrings you’d like to wear. We used these insights to craft our value prop: connect ear piercing with aftercare and earring shopping to create an end-to-end Earscaping® experience.”

A “build it and they will come” approach skips over work that’s essential for any startup. Distilling your brand strategy, sharpening your value prop, listening to your target customer on why they are hiring you, and then clarifying how you’ll communicate all of that back to your customer is foundational — not optional.

4. Double-check on product-market fit before hitting the brand gas pedal.

Time and time again, Bubbers sees founders eager to rev up their engines and get rolling on the road before thoroughly testing if their product is needed in the market. “You have to start with a truly great product that the customer has a need for. Then you can leverage great branding or cool design that can only make it better,” Bubbers says. 

If product-market fit isn’t there, no amount of celebrity and branding is going to make your startup successful.

More specifically, Bubbers sees founders who fail to set up the go-to-market systems that will help them evaluate if they truly have product-market fit, and what that means for the next stage of their company. “If you have funding, you can spend a lot of time burning capital, ‘waiting to see’ if you have product-market fit. But there’s a lot of upfront work and checkpoints you can set up to artificially restrain yourself — what are the signals you need to see before you invest more resources?”

“Perfection is the enemy of good here. Find what good looks like for your business — and then be very honest with yourself if you've achieved it or not,” says Bubbers. “When Studs was still just an idea, Anna and I set up a business model and the checkpoints we needed to hit to keep going. For example, we would say, ‘When our first store opens, we need the company to look like this before we go open up another store,’” she says. 

“We eventually landed on store payback as our single metric. Fast forward to today: Our stores pay back very quickly, and are profitable at the unit-level. Same thing when we layered on e-commerce later — we needed it to break even, it couldn’t be a loss leader.” 

When founders aren’t in market yet, they can get really distracted with making swag, polishing their OKRs, and adding on all of these bells and whistles, like tracking revenue in Tableau. You don’t need any of that. Be extremely rigorous and cutthroat about what is and isn’t working.

FAIL FAST, LEARN FASTER: ADVICE FOR  SCALING A BRAND POST-LAUNCH 

The brand strategy flywheel usually goes something like this: Collect enough insight from your customers to launch a brand, pick and choose from a menu of different marketing techniques to spread awareness, retro your efforts to pull out what works well and what doesn’t, rinse and repeat. 

All that to say, what works for a sales-led B2B SaaS startup may not translate into the same success for a D2C retail brand, and vice versa. But there are still lessons to be mined from Studs’ story, particularly on how Bubbers and her team iterated quickly to find what clicked. Below, Bubbers walks us through the four bedrock pillars that propped up Studs’ brand, while sprinkling in some tested tactics that could apply to any startup’s strategy. 

Pillar #1: Spend enough to set the levers in place, but no more 

Test and iterate, those are the only two ways to grow a brand, Bubbers says. “It’s very difficult without any data, so it’s a little finger to the wind, but have some idea of what you think your CAC will be. At Studs, we had hypotheses about what it would cost to get people into our stores, as well as goals around utilization, revenue and foot traffic for the first few months. We thought, ‘If we can hit these metrics, our stores will have best-in-class retail metrics.’” 

Bubbers then narrowed down her budget but packed it full of different marketing experiments to help Studs avoid wasting time on failed tests later. “In the beginning, I pushed for a budget that allowed us to do enough marketing tests where I could learn my levers, but was low enough where it felt very de-risked. With around $75K, it was a blend of Instagram ads, local wheatpasting, influencer events, and so on, enough to launch in one market,” she says. “We were able to amass a lot of data and learnings to back up greater marketing investments early on.” 

Bubbers shares a few of her lessons here:  

• Ask early on for feedback. “‘How did you hear about us?’ If you ask that simple question to your first 100 customers you’ll easily know which marketing lever you set up worked, be it your influencer strategy, physical ads, email marketing or word-of-mouth.” One interesting thing we learned is that customers referenced our wheat pasting more than I thought they were going to. People would say they came in because they saw our ad outside. With those early indicators, we were able to rely way less on paid digital advertising — something that would have been very easy and almost expected to sink a lot of upfront resources into.”
• Send out brand surveys. “Similarly, it’s easy to survey your customers with an NPS to find out what their experience was like. You can also give them a brand survey and find out if your value prop is resonating. Ask questions like, ‘Why did you come to us?’ ‘What did you feel about the brand?’ Benchmarking these things early on against your hypothesis is really important.”
• Create buzz with strategic influencer and creator marketing. “At Studs, if you were part of our target demo it felt like you 'saw Studs everywhere,' when in reality we had strategically saturated the brand with the influencers, journalists and celebrities and creators our target customer was following.”

Pillar #2: Educate to Innovate: How Content and Branding Cut Through the Category Noise

More often than not, founders are working within a space where they aren’t reinventing the industry wheel, but rather putting a new spin on it. But there are still ways to cut through the noise of a crowded market, and outstanding brand work is one of them. 

“If you have a million other SaaS businesses you are competing against, people need to understand why they should be choosing you over someone else. Brand is one of the best ways to differentiate yourself from the pack,” she says. 

“We did not invent ear piercing. There are many places to get your ears pierced in New York. So for us to differentiate in the market and create an offering, I spent a lot of time investing in the brand, the IP and the design of the experience,” Bubbers says. 

“I knew I needed to brand the entire journey of ear piercing and make it clear that what we're doing is different than just going to the tattoo shop around the block. Our idea was to create a full end-to-end journey around piercing to buying. The way to connect these steps was to provide customer value around aftercare healing content and incredible customer service.” 

Bubbers had the clever idea to coin (and trademark) the term Earscaping — language they could use to describe the entire ear piercing journey, from curating a look and piercing new holes, to healing and uniquely styling an ear with jewelry. 

“People seemed to understand the word and it started to take off in popular culture,” Bubbers says. “I started seeing customers use it, the media used it, and it helped differentiate our brand and elevate our offering.”

But an innovative model and an invented term come with the pressures of creating a new category. “Branding for a category creator is an interesting balance because, on the one hand, you want to use language and vernacular that the customer already understands,” Bubbers says. “If you do invent a new IP, you have more of an uphill battle. You are introducing an entirely new concept, and no one will know what that is.”

It takes a lot to be a category innovator and leader. If you do choose to go that route, you have to be willing to set aside the resources to consistently educate your audience.

As part of Studs’ strategy, Bubbers decided to heavily invest in content, with a focus on education. “We launched an entire content franchise called (Ear)ducation that lives natively on our website. We have earscaping content that educates the customer on piercing placements, healing times, our materials, and new trends,” she says. “To power that internally, we've developed graphic systems and social media narratives around these things so that we can then constantly have a content marketing engine,” Bubbers says. 

When you are building in a new category or inventing something entirely new, invest in brand, content and audience education first. When it clicks for people and they understand what you are making, that’s when you become a category leader.

Pillar #3: Pick where you’re going to play — and let influencers and content creators do the heavy lifting 

“Anna and I decided early on that the community, not us founders, were going to be the face of the company,” Bubbers says. “So our entire approach to social media has been to inspire our community. We quickly learned people wanted to see variety and the best part was there are infinite ways to style your ears, meaning we have an endless pool of ideas to generate new looks and content.”

Here’s what that looks like: “On Instagram, our customers are looking to get inspired and they're very inclined to shop. They love our Earscape images and they like our educational content. So we have these silicone ears and these bright colors. We invest in grid content and we invest in reels,” she says. 

One thing I’ve found about social media channels: You have to test your ideas, of course. But then once they work, you have to repeat them — over and over again.You have to really commit to the bit.

While Studs’ website content and social channels are more aspirational and educational, its influencer program has slightly different goals. “It’s a performance channel, so we’re trying to reach and activate new customers. Our main focus is finding influencers who we think can efficiently acquire new users,” Bubbers says.

The criteria for who her team chooses to partner with is based on typical reach benchmarks and engagement metrics, but Bubbers does start off by asking a single question: “If this influencer showed their Studs experience, either purchasing online and styling their ears at home or visiting us for a piercing at a Studs store, how likely would their unique audience be to engage with our brand?”

But not all the influencers Studs chooses to partner have supersized followings — in fact, they may not even be considered “influencers” at all. What matters is the enthusiasm for ear piercing, and if they are connected to the right micro-communities. 

“On platforms like TikTok, we found that people were already making ‘earscaping’ content on their own — with no association with Studs,” she says. “A lot of users were talking to their followers about which piercings they have, or where they put their earrings. It wasn’t the biggest content creator following on TikTok, but that community already existed. We leveraged that natural virality that was organically happening and asked those creators to make content for Studs, instead of trying to make our own. Now, they post about how they love to get their piercings at our stores, or they make content about how they use Studs earrings to style their ears.” 

Her biggest tip for founders here is to examine the space they are building in and gauge how much outward enthusiasm already exists — it just might lead to a lower-lift social media strategy. 

If there is a natural community niche built around the product or service you are selling, don’t spend your energy trying to create your own videos. Find those who are already organically talking about your product or your market and partner with them instead.

That brings us to another related piece of advice Bubbers gives here, especially for first-time founders exploring social media: Get picky about which channels you spend your time on. 

“We happen to have an experience where people want to follow along with someone going to do an activity. They are watching to see a before and after. That is something that’s easily consumed on TikTok. The mistake founders make is to launch on every channel,” she says. 

“Studs has never launched on Twitter, and we won’t because folks aren’t getting inspired about ear piercings there. We’re not going to start a podcast, either. But for example, there are conversations about ear piercings happening on Reddit — on how to avoid infections and so on — so that could be a place to invest in in the future,” she says. “Understanding the channels and why you should be on them is essential — and it’s also what helps you stay lean.”

Find the Venn diagram of where your target customer is, and where it makes sense for you to be. Where do you have a natural content strategy that you can actually execute and really invest in that early stage, versus trying to be everywhere, poorly, all at once?

Pillar #4: Use experiential marketing to differentiate and scale 

On top of the table-stakes social media and content marketing, Studs has done plenty of off-the-wall experimenting, too. “Now is a great time to invest in offline marketing and eventing because advertising costs are expensive,” Bubbers says. “Digital advertising has become very, very crowded — and it's becoming less efficient. Customers are now in a mindset where they are looking for experiences and activities.” 

Take this recent example: In the fall of 2023, Studs hit the road with a mobile piercing trailer and headed out west, where the reality TV convention “BravoCon,” had gathered 30,000 fans in Las Vegas. “It was a non-traditional way to think about advertising,” Bubbers says. 

She finds experiential marketing to be one of the most effective ways to elevate your brand from the rest of the pack — although the physical storefront experience lends her a natural advantage here, of course. “Our business is unique in that our stores themselves are marketing engines,” Bubbers says. 

But it took a lot of behind-the-scenes work to make that a reality. All of Studs’ 20+ stores were intentionally designed to promote user-generated content, and adhere to a strict aesthetic and design. “I spent a lot of time making sure the stores were highly ‘Instagram-able.’ We paid attention to every detail, like if the shelves were the right material and color, what merchandise was on display, adding the right amount of eye candy and opportunities for ‘selfie moments,’ that would be shared on social organically,” she says. 

Leaning on the stores as the core component of Studs’ brand also meant they could collect customer feedback in real-time, and quickly adjust as needed. “For example, we had a hypothesis that people wanted to shop for earrings with a sales assistant at the ‘Earbar.’ What we figured out over time is that if people aren’t in the stores for a piercing and just wanted to shop for a new pair of earrings, there was too much friction for them to be able to checkout quickly. So we pivoted,” she says.

Experiments have a different shape these days. “Now, we are five years in, and we’ve grown into a new focus of selling more units per stores. So now we’re looking at things like, ‘What adjustments can we make on the walls?’ or ‘What will get higher conversions?’” 

But you don’t need a physical storefront (or even a retail business) for an experiential marketing campaign to make sense. “It all depends on the type of brand you are trying to build and where you are in your company lifecycle,” Bubbers says. “Especially for B2B and SaaS, inserting yourself into cultural moments, whether it’s F1, Coachella, or Art Basel — if that's where your customers are — can be a great way to cut through the noise and earn more brand equity than you’d get from an Instagram ad.” 

You can also think of creative ways to stitch your online and offline presence together. “We ran a campaign selling ‘mystery earring’ bundles during Cyber Week that did quite well. So in our Nolita store, we brought in a gumball machine to recreate that experience in the real world — you’d put in your token and wouldn’t know what you got until you opened it up.”

Drawing from this time of trial and error in physical stores, Bubbers shares her biggest tips for any type of business trying its hand with experiential marketing:  

• Turn the tap on and off: “There are certain times where experiential marketing makes more sense than others,” Bubbers says. “But you have to learn when to turn the tap off and on. This type of marketing lends itself to those strategic moments where you’ll get the most impact. Launching the company is a great time to experiment with offline advertising and experiential marketing to help people know that you exist in the first place,” she says. “And then you can dial it up again later on, once you have organically acquired your early adopters and are looking to get to that next ring in your concentric circles.”
• Crisp up your goals: “Maybe you want to penetrate a new market, increase your web traffic, or grow your social followers. Whatever it may be, founders need to have something associated with their experiential marketing campaigns,” she says. “We did a giant digital partnership with the Instagram celebrity gossip account Deuxmoi earlier on because we were trying to drive top-of-funnel brand awareness for Studs.com. But when we wanted to put all our energy and resources into increasing foot traffic to our stores, we did an in-store vending partnership with Shake Shack to reach that metric.”

Discipline and strategy is crucial when it comes to saving money and resources in branding. Before kicking off any brand marketing experiment, create a hypothesis around the impact you’re looking for.

WRAPPING UP: CONSIDER ADDING A MARKETING WHIZ TO YOUR FOUNDING TEAM 

There’s a long line of founders who come from product and engineering backgrounds — founders who came up in the marketing org are few and far between. While early-stage teams without any marketing expertise are quick to farm off their branding to outside help, Bubbers makes the case for putting more brand and marketing leaders at the helm:

It’s hard to trust consultants, agencies, and freelancers with something as important and personal as what your brand looks, feels and sounds like.

Not only are you putting an incredible amount of trust in folks building your brand who aren’t living and breathing your product, but you’re also missing out on a startup’s greatest currency — speed. “If you own your marketing in-house, you don’t have to go through the operational cadence of briefing and waiting for the work to come back, reviewing, getting to market and reporting. That’s a big ordeal when you are trying to get an early read on whether or not your company is successful.” 

She urges marketers thinking of joining an early startup to take stock of their own skills.  “If you are a marketer who has a really strong sense of brand voice, is extremely customer-centric, knows how to differentiate in a market, and is focused on acquiring — and retaining — users, those are incredibly valuable skills even at the earliest of stages.” 

This article is written by Matt Lerner, co-founder at SYSTM, a company that helps startups “find their big growth levers” (and pull them). Previously, he was an investor at 500 Startups and ran B2B growth teams at PayPal. He previously shared an excellent guide to finding language/market fit here on The Review. Today, he’s generously sharing a chapter from his new book “Growth Levers and How to Find Them,” penned for, as he puts it, ​​“impatient founders and their teams.” For more of his insights, check out his 2-minute newsletter.

Every great startup made wrong turns before unlocking hockey-stick growth. How many wrong turns will your startup need?

As a thought experiment, let’s imagine we know for certain that you need to make precisely 1,000 wrong moves, and, after 1,000 failed experiments, attempt 1,001 would be the one that catapults you to decacorn status. If you knew that from Day 0, how would you run your business differently?

You would experiment like crazy. Every team. Ten tests per week — per employee. You’d hire data scientists and maybe even actual scientists. You’d teach everyone to properly set up experiments, find statistical significance, and look out for type I and type II errors. You might even get a tattoo of behavioral scientist Daniel Kahneman.

Of course it’s not 1,000. We can't know the actual number, and it won’t be so binary. But what does that change? Regardless of whether that number is knowable, in the early days of any startup, you need to learn a bunch of things the hard way. Why not do that as fast as humanly possible?

This sounds obvious in theory. Nobody sets out planning to move slowly, waste time on bad ideas, and test nothing. But in reality, we’re all a bit overconfident, so we tend to go all-in on our favorite ideas and only experiment at the margins, rather than experimenting constantly with bold swings. 

Back when I was a VC, I saw this pattern over and over again in the go-to-market section of pitches. Instead of focusing on big opportunities, founders were recycling a tired list of basic growth ideas that would never amount to much. Instead of finding big growth levers, they were pulling the small ones harder and hoping for the best.

Great startups don’t waste time on small stuff. Every early-stage company works hard, but great startups prioritize incredibly well.

Here’s what I mean by big growth levers: Early growth at startups comes down to a few insanely successful tactics. If you look back at the early days of any great startup, you’ll see that 90% of their early growth came from 10% of the stuff they tried. Some famous examples:

• Airbnb wrote a script to automatically post each new listing to Craigslist bringing them loads of free qualified renters.
• PayPal wrote a script to message eBay sellers, pretending to be a buyer, to ask if they would accept payments via PayPal. Sellers thought their buyers wanted PayPal, so they quickly added the payment option.
• Canva created thousands of SEO-optimized pages with design templates and tutorials because they realized many basic design tasks start with a Google search like “award certificate template.”
• Facebook and LinkedIn created an onboarding process in which new users automatically invited friends and colleagues to join.

This phenomenon is no coincidence — it’s physics. Big companies can grow by deploying heaps of cash and armies of people, using every channel, hoping one will work, and not really understanding which ones do. But startups with a few employees, a couple million dollars, and 1–2 years of runway don’t have that luxury. They need to find the small actions that bring huge numbers of customers, quickly.

For startups, finding big growth levers is a matter of life or death. Most startups never find them, and they die.

“Find” is the operative word there — this process is fundamentally a search. And in a search, your chance of success depends above all on one factor: the pace and quality of your learning. Reflect back on your team’s work these last several months and the growth experiments you’ve run. More specifically: 

• How satisfied are you with your team’s rate of learning? Do they tell you new things about your customers every week?
• How often do they challenge your strategy with new information about the market?
• When an experiment fails internally, how does that conversation go? Does your team talk about what they learned? What they’ll do differently next time? Or are people afraid to tell you about their mistakes?
• Is each misstep making you smarter and moving you closer to success?

Before you can become a “growth machine” you need to become a learning machine. The first overarching goal is to turn your startup into an instrument for discovering your big growth levers. In my new book on growth levers, I recommend three steps: 

1. Understand your customers using Jobs to be Done
2. Map your growth model to help you find points of leverage so you can identify and prioritize the most impactful work
3. Rapidly experiment to find what works best.

While I cover the first two steps in the first half of my book — with step-by-step instructions for interviewing your customers and mapping your growth model — the “rapid experimentation” part of the equation is my focus here today, because it all comes down to the pace of learning.

If the stuff you're doing now is not having a big impact, and nobody's learning from it, then it isn't magically going to start working. If you have found a big lever, congrats, focus everybody on it. But if you haven't, then focus on finding one, not just pulling the small ones harder.

To help you accelerate the pace and quality of learning across your whole team, I’ve open-sourced my chapter on running growth sprints below. I’ll cover how they differ from product sprints, how to prioritize your experiment backlog, and the ingredients of a good hypothesis. Importantly, I'll also dig into how to close the loop by extracting learnings, debugging failed attempts, and empowering your team to run faster and bolder tests. Let’s dive in.

THE CASE FOR GROWTH SPRINTS

Product teams run agile sprints with groomed backlogs and acceptance criteria. They’re fast, deliberate, and reflective — nothing happens by accident. But on the go-to-market side of the house? We’re still making annual plans and huge, expensive campaigns. And prioritization is unsystematic. Should we rebrand? Try LinkedIn ads? Online events? TikTok? Influencers? 

While product sprints are a well-oiled machine, most marketing is still a slow (and expensive) exercise in trial and error — which is bewildering because eventually every company’s success hinges on customer acquisition.

That’s why if you haven’t already, I strongly encourage you to add on growth sprints as a core company ritual. My preferred approach (which I outline in full below) is a simple 5-step mix of agile and the scientific method, but unlike product sprints, it involves the whole company, not just product and engineering. For example, I’ve seen customer success teams make a big difference here. And back when I was at PayPal, we cracked a $100M churn problem with targeted action from our operations team. Zero product, marketing or engineering — only a spreadsheet, a bit of SQL and a physicist named Ben.

The growth sprint process has four goals:

1. Align the entire company (not just marketing or product) around growth
2. Prioritize the most impactful work, with the greatest potential upside (regardless of cost)
3. Rapidly test the most promising ideas with experiments to discover what really works, including finding the best messages and channels, and isolating the ideal target customers
4. Disseminate what you learned from each experiment to accelerate the pace and quality of learning across the company

Each experiment aims at testing a specific hypothesis. These go beyond simple A/B tests; you can use them to validate new product or feature ideas, possible new customer segments, or even business processes.

This requires rightsizing your expectations, however. Unlike product sprints, most growth experiments fail, so your primary outcome is learning — especially from the failures. If the experiments are well designed, failures will help you eliminate bad options and focus your efforts. With enough persistence, patience, and a bit of luck, you’ll find winners, and your data will give you the confidence to double down on them.

With every growth experiment, you're not just trying to optimize your return on ad spend, lower your CPA, or bag a few new logos ahead of the next fundraise. You're fundamentally learning and making progress toward a simple question: How are we going to grow this business?

To get more granular, I follow these steps when running a growth sprint: 

1. Inputs: Gather your customer insights and the data in your growth model, plus any past experiments or ideas.
2. Ideation and Scoring: Triage your ideas to create a shortlist for consideration in the current sprint cycle.
3. Selection: Select the most promising ideas to test.
4. Experiment: Design and run your experiments.
5. Learn: Learn from the experiments, document, and share your takeaways.

You can adapt the process to the particulars of your business — team, tools, org structure, and culture. Some growth teams need engineers; some don’t. Some companies track growth ideas in Jira, some use Trello, and some use sticky notes. Some teams have growth meetings on Tuesdays, some on Fridays, and some every two weeks. I will cover none of these details. 

Instead, I’ll discuss the core principles and goals of the process and the rationale for each step. That way, you can adapt the process to your existing workflows because the best process is the one you’ll actually use.

STEP 1: GATHER YOUR INPUTS

Your big levers are seldom obvious. Generic tactics like paid ads, SEO and referral programs will only get you so far. Growth levers are unique to each startup’s specific, unexpected learnings — so every sound hypothesis for a growth experiment must start with a customer insight.

For our purposes here, I’ll assume you’ve already done the hard work of interviewing your customers and mapping their journey to your product, gathering tons of ideas for experiments in the process. (But if you’re starting from scratch, the TL;DR is that I recommend following the jobs-to-be-done approach to surface customer insights. You can read this quick JTBD primer here on The Review, but Chapters 2-4 of my book will also help you find your way.)

To give you a sense of how customer insights can translate into growth experiments with real results, here are a few examples from companies I’ve worked with:

• Photobook app Popsa figured out that prospects were suspicious of their product category, because photobook apps are notoriously tedious. They changed their tagline from “Fast easy photobooks” to “Photobooks in 5 minutes” and quadrupled installs.
• FinTech app Rebank realized that most of their prospects — all startups — had basic finance questions before they were ready for Rebank. So they published a detailed free guide, “Finance for Founders,” that generated thousands of qualified leads and helped them grow 22X in 18 months.
• FATMAP offers 3D terrain maps for hikers and backcountry skiers. Customer interviews revealed that most trail map searches start on Google. So they published every trail, route and piste in their database in the form of 100,000 keyword-optimized web pages. That brought in an additional 80,000 qualified prospects per month.
• Scheduling app Cronofy discovered five niche use cases among their most loyal customers, like booking HIPAA-compliant medical appointments. They replaced their generic “book a demo” homepage link with those five options, and quintupled their conversion rate.

STEP 2: IDEATION AND SCORING

With your ideas gathered, the next step is a triage: quickly filtering down the backlog of ideas. Your team should have many ideas based on information from customer interviews and your data. You need to sort through them quickly and find a few that can have a huge impact.

Looking at the list of ideas, score each one quickly on three factors: 

• Key Driver: Key drivers represent the results of the work people do to move the North Star, but not the work itself. (For example, you could break a measure of weekly active users into three drivers: signups, activations, and retention.) So if a growth experiment you’re considering works, which of your key drivers will it most directly impact? Traffic? Conversion? Retention? Referrals? Activation?
• Impact: If it works, how big would it be, on a scale of 1 to 5? For example, if you’re considering an SEO project, and the search term you’re chasing only gets 10 searches per month, that number limits the potential impact. Or if you’re considering changes to your pricing page, but only 2% of your traffic ever visits the pricing page, that change will only affect 2% of your traffic. (Don’t overthink this, just make a quick order-of-magnitude estimate. It’s very hard to do this accurately, and it’s not worth the extra time and effort.)
• Effort: How much time, effort, money, and engineering would be required? Blend those costs into one number from 1 to 5. Again, estimate quickly, don’t overthink it.

Here’s an example of a growth idea backlog:

Next, remove ideas that don’t move your key drivers. Among the remaining ideas, start with those that impact your rate-limiting step. I dive into rate-limiting steps more deeply in my book, but essentially, it’s a bottleneck that constrains the overall growth rate of your business. For example, for a meditation app, if 95% of new signups churned after their first time using the app, it would make no sense to invest in finding more traffic, improving conversion on the landing page, or building a referral program because the onboarding experience is their rate-limiting step. 

A good way to isolate your rate-limiting step is to ask: “If we double our performance in this area, will we double the business?”

Finally, sort by potential impact, from most to least. You’ll gravitate toward high-impact and low-effort ideas, naturally. But keep the high-effort ideas on the list. We’ll talk about how to test them further down.

STEP 3: SELECTION

The scoring process will shorten your list of ideas, but you’ll still need to choose a few to test each week. If you can test more, great. Run as many good experiments as you can with your resources. Sometimes one test requires engineering, another one is just design and copy and the third is a customer service treatment, so you can run them all in parallel. But if all your ideas are landing page tests, then you’re more constrained. I find that fast-moving teams often set a goal of 3-5 per week.

Here are some prompts you can use to decide which experiments to run:

• Which of these, if it works, could have the biggest impact?
• Will we learn something important about our business or our customers? Will this resolve an internal debate we’ve been having?
• Is there an easier way to get that information, such as studying our existing data, asking customers, or speaking to our salespeople?
• Is the idea actually risky? Could it backfire? Or is it expensive in terms of money, time, engineering work, or some other scarce resource? (If not, maybe just do it rather than run a formal experiment.)
• Do you have the resources and technological capability to run this experiment well?

The more data you have, the easier this decision will be. If you’re finding these decisions difficult and contentious, try to identify the missing information that would make it easier to decide.

STEP 4: EXPERIMENTATION 

What’s the difference between an “experiment” and “just do it?” The difference is only about 5 minutes, but it’s an incredibly valuable 5 minutes. That’s the time it takes to write a hypothesis and make a prediction. Documenting your prediction helps clarify your thinking and eliminate hindsight bias. That way, no matter if your experiment succeeds or fails, it will make you a little bit smarter.

Does everything need to be an official experiment? We don’t always have the time, tech, or traffic to run a proper, controlled experiment, and that’s okay. Sometimes, “just do it and see what happens” is a perfectly good approach. But every project, whether you get a clear winner or not, needs to bring learning.

Do the upfront thinking it takes to ensure you learn from your experiments — always start with a clear hypothesis and prediction.

Formulating a hypothesis

Writing a hypothesis only takes a few minutes, and it’s a great way to clarify your thinking. Here’s the format:

• The Risky Assumption: We believe that ______.
• The Experiment: To test this, we will ______.
• The Prediction: We predict that ______ (metric) will move by ______ units in ______ direction.
• The Business Effect: If we are right, we will ______. Think: how will this change the way you run your business? If you can’t think of anything you’d do differently, it’s probably not worth running the experiment.

Start with a hypothesis that contains a single risky assumption that can be tested and measured. For example: “We know that app users have better retention rates than web users, and we believe this is causation, not correlation. Therefore, if we encourage new signups to install our app after they register, rather than using our web version, we predict it will increase our 90-day retention rates from 8% to 12%.”

Avoid bad hypotheses

The most common reason experiments fail is starting with a poor initial assumption. A good assumption contains a belief about your customer that’s rooted in some insights you gained from your data or customer conversations. 

A very common mistake is to draft a circular hypothesis like this:

We believe that if we lower our price by 10%, we will get more signups. Therefore, we will offer a 10% discount, and we predict our total sales will increase.

A circular hypothesis basically just says: “I have an idea, I think I’m right, so I’m going to try it, I predict it works.” Testing them doesn’t help us learn.

If you ran that 10% discount experiment and it failed, what would you do next? Lower the price more? Revert to the original price? Raise the price? And if the experiment succeeded, what would you do next? Lower the price further? Keep the discount and move on to another unrelated experiment? It’s hard to come up with a next step because this experiment hasn’t tested any assumptions about your customer.

A better hypothesis would focus on an assumption about our customers’ beliefs that we wish to clarify or validate. For example, in the case of our 10% discount, what customer beliefs would need to be true for a 10% discount to be a good idea?

Perhaps we believe most of our prospects like our product but aren’t buying because it’s slightly too expensive. Therefore, if we lower the price by 10%, it would be within their acceptable price range. If that were true, then a 10% discount would be a great idea.

Alternatively, maybe we believe most prospects like our product but lack urgency around the purchase. Therefore, if we offer a small discount with a deadline, we can use that deadline as a forcing function to move prospects across the line. The truth is both of those hypotheses sound kind of basic because this 10% discount idea was a generic tactic, not rooted in any real customer insights.

Therefore, as you draft your hypothesis, start with an assumption about your customer rooted in your customer interviews, like these examples:

• We believe prospects are not buying our product because, based on our home page headline, they do not understand how our product will help them. Therefore, we will test versions of our headline that more clearly describe, using actual customer language, the top outcomes that a prospect can expect from using our software.
• We believe prospects are not clicking “book a demo” because they are still in the information gathering and comparison stage of the purchase journey, not yet ready to speak with a salesperson, as “book a demo” implies. Therefore, in addition to “book a demo,” we will offer visitors the option to download a buyer’s guide to help them understand our product category so they can feel like they’re making a more informed decision.
• We believe prospects are not downloading our "buyer’s guide” because they think it’s biased in our favor. Therefore, we’ll commission a respected independent industry expert to author our buyer’s guide and create a visual design that does not reflect our branding.
• We believe prospects are not signing up for our product because they are worried it won’t work. Therefore, we will surround the “sign up” button with customer testimonials that call out people’s specific results, and we will highlight our money-back guarantee.

You’ll notice these are all negative hypotheses (e.g., “We believe prospects are not doing X because…”). A negative phrasing reduces the risk of writing a circular hypothesis. Statistical researchers always try to disprove a null hypothesis (e.g., we believe income and education are not correlated). Doing so reduces the risk of confirmation bias. 

Most growth experiments aim to convince people who aren’t doing a certain thing to start doing it. Ideally, those experiments rest on a theory about why they’re not doing it in the first place.

Next, describe your experiment at a high level: “We will randomly split new signups and redirect half of them to the app store, and allow half of them to stay with our current mobile web experience.”

Then, choose a success metric that’s deep enough in the funnel to be meaningful (e.g., not “clicks”) but shallow enough to get your data quickly. For the app retention experiment, maybe your primary metric is one-month retention rates. But also keep an eye on the number of logins, transactions, or some other behavioral metric, and track long-term retention metrics as the cohort matures.

Place your bets

Now, make a specific numerical prediction. For example:

“We predict that month 2 retention increases from 38% to 50%.”

You need a specific numerical prediction because your estimate of the impact will be used to calculate your sample size. Pick a big target. If the experiment won’t have a big impact, it’s not worth your time.

Finally, consider the business effect. What action(s) will you take if your test is successful? For example, maybe you’ll create and launch an Android version of the app and push new signups to install the app. Also, what if the test fails? Maybe you’ll remove the interstitial that sends people to install the app.

Write down your hypothesis and share it with as many team members as you can. Encourage them all to make predictions or even “bets,” giving a prize to the winner. It’s a fun competition that helps everyone learn about the business, your customers, and the experimentation process in general. It also reduces the chance of people saying “I knew that all along” when the results come in. Instead, they’ll have to reconsider their past assumptions.

Run small tests of big ideas

You’ll quickly test your “high impact, low effort” ideas, but what about those high impact and high effort ones? Often, the best ideas are hard or expensive, but that’s no reason to rule them out.

If you don't test big things, you won't find big levers.

When working with startups at SYSTM, we encourage teams to start with the biggest-impact ideas — regardless of cost or effort — and dream up ways to test them with small, quick experiments. That’s the secret: small tests of big ideas, or minimum viable tests (MVTs). (My friend Gagan Biyani, founder and CEO of Maven, wrote an excellent guide to MVTs here on The Review that goes quite deep, but read on for my take below.)

Consider these two examples:

1. Airbnb’s founders suspected better photography might improve rental rates. But sending professional photographers to every property would have been complex and expensive. Fortunately, Airbnb was founded by design students, so they grabbed their cameras and spent a weekend photographing only the listed apartments that were near their base in New York City. They found their professionally photographed listings rented faster and for higher prices. That result justified a larger rollout with professional photographers across their properties.
2. An ecommerce app was debating adding PayPal to their checkout flow, but the integration would’ve required scarce engineering resources, and PayPal was more expensive than Stripe. To quickly test the idea, they added a PayPal button to their mobile web checkout flow without actually enabling PayPal. (If people clicked it, they were prompted to enter their credit card details). They found that about a quarter of their shoppers clicked the PayPal button, and many of them abandoned the checkout when they realized they could not actually use it. This gave the team the data they needed to justify adding a PayPal option.

It’s fine to score growth ideas based on effort and impact. But don't disregard the “high effort” ideas. Instead, find a quick cheap easy way to test them.

If you have a big idea that’s hard to execute, instead of testing the whole idea, you’ll start by quickly testing only your riskiest assumption. Start with a pre-mortem listing all of your risky assumptions. 

Imagine that the project has failed, and list all the possible reasons it could have failed. Most risky assumptions fall into these three categories:

• Lack of customer interest: Mistaken assumptions about what our customers want or how they would behave.
• Poor execution: Some things are harder to execute than we assumed, either experimentally or at scale.
• Small market: Some ideas can be executed, and customers love them, but the opportunity is smaller than we realized.

If you’re stuck here, your investors can probably help you spot your risky assumptions — they’re rather good at anticipating what might go wrong. After you’ve listed all your risky assumptions, try to narrow down the list to the single riskiest one. Then, write your hypothesis and design an experiment to isolate and test that particular assumption rather than the whole idea.

Thinking honestly and clearly about risks is a rare and useful skill.

Here are some examples of clever MVTs:

• Landing page test: Before you build the product, create a landing page, buy some qualified traffic to it, and see if anyone clicks “buy” or “sign up.” (If they do, apologize that your product isn’t ready and add them to your waiting list.)
• False door test: Instead of adding a product feature, add a button for the feature and see if anybody clicks it. If they do, apologize and let them know the feature is not yet available. Maybe ask them what the feature would enable them to do?
• SEO: An effective inbound / content / SEO strategy can take a very long time. But you can validate the idea quickly with a keyword research tool. Take your search terms and check how much traffic they get each month, how competitive the term is, and which pages currently rank. Are there many searches? If you create good content, could you rank in the top three? Next, build a landing page and pay for some traffic to see if it brings you good-quality prospects.
• Concierge: Before you build a complex product or feature, try delivering the service manually. For example, I worked with an early-stage startup developing a training app. They hoped adding notifications would boost usage, but they had a long product roadmap and only one engineer. The co-founders downloaded a list of all users and their phone numbers, and randomly sent WhatsApp reminders to half their users, leaving the other half alone. The half who received the messages activated 450% more often than the control group, and building notifications became an easy decision.

STEP 5: LEARNING FROM EVERY EXPERIMENT

If the experiment works, great! Take the time to understand why it worked, and think about what you’ll do next. But most of your experiments will fail — or at least surprise you. (If they don’t, you’re not being bold enough.)

 Take the time to look through the data, note any surprises, and discuss the results with your team. Each team member understands different parts of the puzzle. Some are experts on tech. Others are closer to customers, the data, or “best practices” in a field like product or marketing. Bring all their knowledge together.

Here are some prompts for your discussion:

• Did anything unexpected happen?
• Any theories as to why that happened?
• What did we learn about our customers?
• What did we learn about our proposition?
• What did we learn about our own thinking / assumptions?
• What did we learn about our ability to execute?
• What did we learn about our tools and process?
• Were any new questions or hypotheses uncovered?
• Is there anything we should start or stop doing?

And here are some prompts to consider the next steps: 

• Is there any value here? Should we expand, repeat, or scale this?
• Is there anything we should now stop doing or cross off the list?
• Are any follow-up experiments needed?
• What implementation details should we change?
• Do we need to change any of our KPI definitions?
• Who else needs to know about this result?
• Are there any operational takeaways about how to run experiments better in the future, e.g., tracking or experiment setup?

How to debug a failed experiment

If your post-mortem discussions are full of debate and speculation, your experiments aren’t making you smarter. A scientist or engineer would analyze an unexpected result piece by piece to isolate the problem. You can do the same: Step through the whole experiment, isolating each possible point of failure. 

For example, maybe you ran a paid social ad that pointed to a landing page with a sign-up offer and got very few signups. Here are some possible failure points:

• Targeting: Did the test target legitimate prospects?
• Attention: Did the test catch their attention? Or did they scroll past it to get to the next zany pet video?
• Readability: If they saw it, was it clear and readable enough? Did they literally parse the words?
• Comprehension: If they read the words, did they interpret them correctly? Do they understand what you’re saying?
• Trust: Even if they understood your promise to help them, did they believe you?
• Resonance: If they understood the words, did they care? Were they able to connect it to something important in their life, like a struggle, goal, or question they’d been pondering?
• Cost / benefit trade-off: If they were excited about your proposition, was it worth the price? Or was the next step a bridge too far either in terms of financial cost, user experience pain, or even unanswered doubts and fears about your product or category?

You can isolate any one of these causes. For example, you could rule out the Targeting variable by paying a premium for AdWords that targets super high-intent traffic. And you could test Readability by showing your ad to people briefly (e.g., for 3 seconds) and asking, “What did that say?”

A campaign could fail for many reasons. Better to isolate and test each one.

When experiments fail, the root cause is often a muddy hypothesis. So, for the next experiment, get very clear on your written hypothesis and success metric. Isolate one variable (e.g., message or targeting or price) and track the right metric. Or try testing bolder things that challenge your most important beliefs and assumptions about your customers. How can you get your team to be more bold? That brings us to the most important issue of all, mindset.

BOLDER & FASTER: FOSTERING THE DISCOVERY MINDSET

You can run experiment after experiment, but you’ll struggle to get a big lift unless you have the intellectual honesty to examine your beliefs critically and allow your riskiest assumptions to be tested. The process doesn’t work without a discovery mindset.

My team and I have worked with over 200 startups. Some learn quickly, others are painfully slow. The difference — every time — stems from the leaders’ mindsets. More specifically, it’s the ability to shift from feeling confident that you have the right answer to feeling confident you can figure it out.

People don’t like being wrong, it’s scary and uncomfortable. When something doesn’t work, that’s the moment of truth. You need to show up and encourage and praise the learning. Time and again, we see that the most successful teams are the ones who have the confidence to view new information as an opportunity rather than a threat. The discovery process ends with growth, but it starts with learning. 

If you liked this article, check out Lerner’s book, Growth Levers and How to Find Them, available worldwide on Amazon, Kindle and Audible.

For a founding team to achieve startup success together just once in their lifetime is impressive. Twice is remarkable. Thrice? Practically unheard of. That’s part of what makes the story of Jessica McKellar, Waseem Daher and Jeff Arnold so unique. Not only did they build successful startups together three times over (with one acquired by Oracle and another by Dropbox), but they did it while maintaining a deep mutual respect that most founding teams can only dream of.

“Jeff, Waseem and I have complete trust in each other to do what is right for the business,” says McKellar. “It’s a rare thing to experience. I would never let go of it.”

Before they were at the helm of Pilot — a $1.2-billion company providing bookkeeping and tax services to the likes of OpenAI, Lattice and Airtable—they were just three self-professed computer nerds at MIT. “The nerdiest of the computer nerds hung out at the computer club,” jokes McKellar. “And that's where we met.”

Soon after, in June 2008, they started their first business together, Ksplice, which built technology that made it possible to update Linux kernels without rebooting and causing downtime. The trio lived in a rundown row house in Cambridge, bootstrapped the entire operation, grew it to seven figures in revenue and sold it to Oracle in July 2011.

After working at Oracle for a year, the founders were once again itching to start a new venture together. Their next company was Zulip, a pre-Slack group chat app that was acquired by Dropbox in March 2014.

With two successful exits beneath their belts (all before the age of 30), it would be understandable if the trio decided to hang up their founder hats — at least for a while. But after a couple of years at Dropbox, McKellar, Daher and Arnold decided to start yet another company. This time, bigger. This time, one that could go public.

“We wanted one last go-around. We wanted to have the experience of building a company to a later stage than Ksplice and Zulip had reached — a company that is wildly successful and financially transformative,” she says.

But first, they needed to find the idea that would get them there. In this exclusive interview, McKellar (Pilot’s co-founder and CTO) shares the behind-the-scenes story.

EXPLORING AND VALIDATING IDEAS 

When the three founders began brainstorming their next business in late 2016, they were sure of three things:

• They wanted to solve a business problem, not a consumer one.
• Their target audience, at least initially, would be startups and small businesses.
• They would only pursue an idea that all three of them were jazzed about — the founding trio sticking together was a non-negotiable.

From this jumping-off point, they created a list of problem-solutions they thought had potential, mining their past experiences for clues. And, as it turns out, a kernel of the idea for Pilot could be found as far back as 2009 when they were recent college grads bootstrapping Ksplice. 

“We certainly couldn't afford a back office team back then, so we got a copy of ‘QuickBooks for Dummies’ and QuickBooks Desktop software and we tried to do it ourselves. We even wrote some software to try to auto-close the books ourselves. So that experience of having to figure out how to take care of our own finances was a problem we had experienced ourselves nearly a decade prior,” says McKellar

To validate that this problem resonated with a much wider founder audience, they went to startups and small businesses and asked: What are your biggest pain points? Then, they expanded their scope and talked to teams in finance, accounting, legal and HR across a variety of business sizes, from SMBs to mid-market companies. 

The overwhelming, loudest theme that came out of customer discovery was that getting your finance and accounting taken care of was as unsolved a problem in 2017 as it had been back in 2009 when we were at our first startup and trying to do it ourselves.

“That seemed like a thread that was worth pulling on. So we started pulling on it,” says McKellar.

The idea for a bookkeeping solution won for four reasons — all strong indicators that there was a clear path to product-market fit if they continued down this road:

• It was the most prevalent and pressing pain point that came up in customer discovery.
• It was in an enormous market.
• The average sales price (ASP) was high.
• The competition in the space was low.

And so, after some brainstorming and customer discovery, the founders landed on the idea for Pilot, a monthly subscription bookkeeping service for startups. Did they entertain other ideas? Yes, they toyed with building mid-market HR software. Could they have taken the HR software idea and made it a success? Sure. 

“But at some point, you just have to call it. You have to stop talking about ideas and just say, ‘Okay, we're going to try it.’ And what does it mean to try it? It means you try to get someone to pay you. Payment is the true proof,” she says.

GETTING THE FIRST PAYING CUSTOMERS

It was now January 2017. Pilot had no engineers, no software, no bookkeepers. But that didn’t matter. The founders approached their fellow founder friends, verified that bookkeeping was a painpoint for them, and then asked, “Would you pay us $100 to take care of your bookkeeping?”

If the answer was no, they dug deeper to get to the root of their target customers’ hesitation.

But if the answer was yes? “We’d say, ‘Great, please provide your ACH details, and we will become your bookkeeper,’” McKellar recalls.

Believe it or not, no one asked to see their accounting credentials. “It's not like there was some clear, best-in-class provider that all of their other startup founder friends were using. It was totally fragmented. No one wants to go on Yelp and try to find the best bookkeeper for their startup. It's a trust-based decision. And what we had with our friends was trust. We were successful founders, so getting our friends to trust us with their books was no worse than choosing a random bookkeeper.”

With a few yeses in hand, Arnold and Daher started doing their first customers' books manually while McKellar looked over their shoulders and wrote code.

“Doing the books looks like this: You're importing transactions into QuickBooks, reconciling, categorizing. You're dealing with bills and invoices. There's a review process. You have to validate to yourself and to the customer that the books are correct. So we got really familiar with the QuickBooks APIs to figure out what's possible and what systems we would need to build,” she says.

Step one of building Pilot’s software was creating a checklist. "To build these big systems, you need to start getting the shape of the process flow. What are the checklist steps? What are the systems that need to be built? And then you just crank on it."

If you can articulate what needs to happen in a checklist, you can, piece by piece, translate that checklist into software.

As they cranked out code, they juggled dozens of initial customers, tracking them all on a whiteboard. Shortly after, they put up a website that accepted payments. At the time, they were charging $100/month, but as they took on larger customers, they bumped up their pricing to reflect the increased complexity and get the margins they wanted.

“Margin is an important part of how we assess the health and growth of the business because Pilot is not pure SaaS,” says McKellar. A quick point of clarification here — in addition to Pilot’s software, the company employs accountants, fractional CFOs and tax specialists who work with customers in tandem with the technology (more on that decision later). “We're delivering a service on a monthly basis. So we're very tender to margins,” she says.

At the beginning of any business, pricing can be tricky, and many founders just throw out a number to start charging something, anything. But as you get to know your market, you can get it down to a science, as McKellar explains: “We actually have a pretty tidy heuristic for pricing, which is, if you look out in the market, we know that most businesses, whether or not they're using Pilot, spend between a half a percent to one percent of their total spend on finance and accounting. And if you know that, you can build a pricing and packaging model around that.”

LAUNCHING AND FINDING PRODUCT-MARKET FIT

There’s often a lot of buzz around launch day for startups — with plenty of fanfare and, if you play your cards right, flashy headlines. But McKellar places so little importance on it as a strategy that she can’t even remember when Pilot officially launched.“What are launches really for anyway?” she says. “They're mostly about organizing yourself internally; rallying the team around a new feature, product, sales motion or marketing collateral; getting the team excited; and getting it out the door. For the most part, launches don't cause you to generate a bunch of new money. You might see a bump in website traffic or a spike in signups, but only briefly.”

For Pilot, we focus on delivering a service people love. They love it so much that they stay with us, and they tell their friends, who then become Pilot customers. That’s our go-to-market flywheel, and that's how our revenue grows.

But, if you had to pick the date when Pilot officially launched, it was probably January 2019. That’s when it came out of beta and became available to the general public. At this point, the company was already managing the books of more than 150 companies.

Having paying customers is certainly one sign of product-market fit, but what signaled to Pilot’s founders that they were on the right path? A memorable moment was when they started to see proof that their software was doing exactly what they’d built to do.

“Of course, we were using the software that we were building to close Pilot's own books. And there would be moments when the software would catch something that we had missed, like a double payment,” McKellar recalls. “And we’d realize that this wouldn't have happened unless we were using Pilot technology. So the dogfooding of the product internally was very affirming of the route we were on.”

The biggest turning point was when, without even trying, they started getting pulled upmarket and across verticals by their customers—an enviable position for any founder.

Customers kept coming back to us saying, “Can you do more for me? Can you also do my taxes?” That pull suggested that we were actually providing a customer experience that was so valuable that people wanted to not just pay us for bookkeeping but actually to expand the engagement with us.

EXPANDING THE PRODUCT SUITE

Finding initial product-market fit gave the founders the conviction they needed to start adding on new services and pursuing expanded customer segments. 

“Given the goal of the company, which is to be the financial back office for a broad range of businesses, we had to break out of startups eventually,” McKellar says. “Startups are a very small percentage of the economy. Plus, we have the goal of building a company that's going to be independent for a long time and eventually go public, so we need to be on a particular revenue growth curve. We need to get to billions of dollars a year in revenue.”

It goes back to the initial spark for this co-founder trio to start their third company in the first place — with their sights set on building something much bigger than their first couple of ventures. But while Pilot’s founders have aggressive growth goals, they always balance those against their steadfast dedication to customer satisfaction. 

“We're very protective of that go-to-market flywheel that's about the brand and the reputation we have that we can only earn by actually doing a good job. We need to be delighting our customers consistently. So how do we expand safely? Do we have the right instrumentation, the right feedback loops, the right expertise on the team? Honestly, the revenue curve is brutal if your goal is to be on the best-in-class path towards being a public company. Every six months, you're like, ‘Oh shit, what's our next additional revenue stream?’”

First things first: Don't ever jeopardize CSAT. You should never be so desperate to hit your numbers that you sacrifice customer satisfaction. We’re always asking, “What do our customers want us to do?”

Pilot’s founders knew the timing was right for adding a new product because this expansion was led by their customers, who were practically begging for tax services. To determine which customer segments they should go after next, again, the founders let the customer tide pull them in the right direction, looking at who was knocking on their doors and getting turned away. Ecommerce, CG&R and professional services firms were already showing interest in working with Pilot, even before Pilot sought them out.

“That meant that what we were already saying out in the market was resonating with them without us even trying to speak directly to these segments,” says McKellar. “So we decided to learn operationally about these types of larger businesses and figure out the delta from startups so we could adapt to it on the product side and on the service delivery side. Once we felt really confident that we could deliver a high-quality experience, we opened the floodgates from a marketing and sales perspective.”

In April 2019, Pilot raised $40 million in Series B funding and launched its corporate tax preparation service. And less than a year after that, three additional products debuted: R&D Credit, CFO Services and Extended Services.

THREE BIG LESSONS FROM THREE-TIME FOUNDERS

Pilot’s seamless additions to its core product point back to the enormous importance of choosing the right problem to solve. Well into their third business together, McKellar, Daher and Arnold have made the moves of seasoned multi-time founders. So if you’re not one yet, here are three lessons you can learn from these serial entrepreneurs.

PMF Lesson 1: Picking a big market Is first priority

“If you plan to build an enduring company, one that can be independent for a long time, one that can go public, the number one thing you need is a market that's large enough,” McKellar says. “A lot of other things you can change after you've started, but you can't change the size of the market. We’ve tackled smaller markets before. The market for businesses who care about rebootless kernel updates on Linux is a great market, but it’s not huge, which is why Ksplice was always going to end up being acquired. It's just too niche a product to live on its own independently. When we started Pilot, we knew we wanted to tackle a really big market, something that could have legs indefinitely.”

The sneaky genius behind the problem Pilot solves is that it’s an activity that’s legally required for all businesses, guaranteeing demand and longevity. Businesses all have to do their taxes, and to do that, they need bookkeeping.

We chose a problem that literally every business has. Bookkeeping is not a nice-to-have, it’s a must-have. And because of that, it's an enormous market, and our business is resilient even amidst economic turbulence.

PMF Lesson 2: Ensure the problem you solve is the problem your customers actually want you to solve

As three MIT-trained computer scientists, Pilot’s founders easily could’ve built a pure software solution, but by doing so, they would’ve missed the mark of what their customers were actually telling them. By listening closely to what their customers really wanted, the founders decided Pilot would be a combination of people and software.

“From talking with business owners and founders, nobody was saying, ‘Hey, I want more accounting software.’ People were saying, ‘I want to give this problem to someone else and have peace of mind that it’s being solved.’ The feedback was that they wanted someone else to own the problem from end-to-end.”

It’s a hard-won lesson from their Zulip days (their second company together) when the founders built the product they wanted as engineers, not the one that a wide swath of customers wanted.

“There were some companies that passionately used Zulip, like 8-10 hours a day average for the company, per person, and deeply integrating it into their workflows. But for everyone else, it was too hard and complicated. What we built couldn’t generalize to the broader customer base we were trying to target,” she says.

You have to be really careful about overfitting to your own experience. You need to make sure that you're selling something that is going to resonate with the intended audience.

PMF Lesson 3: Build a product that has natural extensions

“One thing that’s really attractive about bookkeeping as an entry point to the back office is that there are a bunch of natural extensions out of bookkeeping: taxes, fractional CFOs, R&D tax credits. It’s ideal to get that all done under one roof so you don't have to deal with and coordinate among multiple vendors. If we're your bookkeeper and your tax preparer, when the tax preparer has a question, they can just go ask the bookkeeper. We have a deep understanding of how Pilot does bookkeeping to make that exchange really efficient and avoid mistakes. There's synergy in the product. It's a better customer experience.”

This natural extension is what enabled Pilot to start with bookkeeping, and then have their customers literally pulling them into other product lines — rather than building second and third products and hoping they’d catch on with the initial customers. 

HOW TO FORGE A CO-FOUNDER RELATIONSHIP THAT CAN GO THE DISTANCE

It’s been said that VCs invest in teams, not ideas — and Pilot’s co-founders are a classic example of why. When it’s time to choose who to start a business with, it pays to choose wisely. Notably, back when McKellar, Daher and Arnold were running Zulip, angel investor and Kayak.com co-founder Paul English didn’t like their idea for a group chat app—but he chose to invest anyway because of the team. 

"Their dynamic was so powerful that I would almost invest in whatever they do," English told CNN back in 2014. (And yes, English is now an investor in Pilot, too.)

So what makes McKellar, Daher and Arnold such a dream team? Let’s dissect the dynamics of this trio. 

1. Separate areas of ownership

Early on, the three founders established separate, non-overlapping areas of expertise. This allows them to be subject matter experts in crucial areas of the business and trust each other to take care of their distinct areas of ownership. This may seem a bit surprising — after all, the trio met as admitted computer nerds at MIT. But there were some nuances that each brought to the partnership beyond a sharp acumen for code. 

“As a people person, Waseem gravitated toward the sales and go-to-market side and was the first salesperson at Ksplice,” explains McKellar. “Jeff is the kind of person who reads corporate tax law for fun. He brings that analytical mind and conservativeness to the business to make sure that we're running it safely. And then I’ve always stuck with the product side, staying closer to the customers.”

2. Alignment of values and motivations

When they started brainstorming ideas for what would later become Pilot, they were already in agreement on wanting to solve a business problem for startups and eventually grow the company to go public. They were only diving back into the world of building from 0-1 with their sights set on a massive outcome.

“We're values aligned about what kind of company and company culture we want to build. And that’s been key to functioning well as a founding team.”

3. The ability to handle conflict well

“Like any relationship, there are ups and downs,” says McKellar. “It probably took Jeff and me a solid seven years to really get along. But why did we start working together? Because we thought we were the most effective potential cofounders that we knew. And why did we stay together? Because we proved that we were so effective as a group. If you have that alignment, if you have that trust, that's so precious. We would never let go of that.”

So even if you and your co-founders are squabbling, ask yourselves this: As business owners, are you able to deliver results together? If you’re consistently delivering the business outcomes you want, you’re proving your effectiveness as a team and are likely able to channel those conflicts into growth.

THE PATH AHEAD

A lot has changed since McKellar, Daher and Arnold bootstrapped their first startup from a mouse-infested house in Cambridge. Today, their third venture, Pilot, is a Series C unicorn with over $150 million in funding and noticeably cushier digs: one office in San Francisco with a view of the Ferry Building and another in Nashville with river views. 

But three startups later, two things have remained the same: the founders’ closeness to their customers and to each other. McKellar still occasionally does bookkeeping herself and hops on customer and sales calls every week. "Nobody should be closer to the customer experience than founders,” she says.

When asked who her most memorable mentors have been during her 15-year career, she says, “My co-founders, Jeff and Waseem. They’ve had a tremendous impact on me, not just as a founder and a business owner, but as a human being. I'm deeply grateful to have been in the crucible of this startup experience for so long with these two people who I have such deep trust and respect for.”

If their venture history is any indication, these founders are not ones to rest on their laurels. They’re forging ahead toward the vision they’ve had for Pilot since its inception in 2017.

“We’re on the path towards building a profitable company,” says McKellar. “That means staying on that revenue curve and continuing to climb upward slowly on those margins. From there, you grind it out. It's kind of a math problem. You know what ARR you roughly need to have by the time you should be going public. You know what your metrics and margins should look like. So the next five years for Pilot will involve continuing to build out that rigor internally, busting our asses to stay on that revenue curve and, first and foremost, delighting customers.”

It’s the first week of the new year, and here on The Review we’re ushering it in with a beloved annual ritual (that we find to be much more delightful than other yearly exercises like annual planning or performance reviews). Before powering full steam ahead into 2024, we press pause and leaf through every article we published in the past year, plucking out our favorite snippets of company-building wisdom. 

It’s actually been a double dose of reflection for us recently — a few months back, we celebrated The Review’s 10-year anniversary with a special compilation of the 100 best bits of advice ever published in our decade-long history. (If you missed it, we highly recommend diving into this trove of wisdom.)

As we assembled that massive guide and revisited the hundreds of articles in our archive, we were reminded of all the ground we’ve covered since The Review’s inception in 2013. Stepping back to apply a decade-long lens, we concluded there’s no one singular topic or theme that makes something “Review-y” — just a focus on finding the sharpest folks who can deliver standout tactics and fresh frameworks that you can use today to change your company and your career. 

But when you zoom in on a specific year, themes inevitably start to emerge. In 2020, it was (of course) advice for navigating the tumult of “these unprecedented times.” In 2021, there was an itch to try something new, as job-seekers pursued new opportunities and funding rounds came together at lightning speed. And just as quickly, the tides turned again in 2022 — with folks facing down uncertainty around layoffs and market corrections.

Many years from now, when we look back on 2023, we will no doubt remember it as the year AI became mainstream. With ChatGPT thrusting us into the generative AI revolution, we explored some of the most pressing questions for startup operators with expert interviews on our In Depth podcast. Here’s a sampling: Bard’s Senior Director of Product Jack Krawcyzk took us behind the scenes of how Google rapidly built its experimental AI tool. Vercel founder and CEO Guillermo Rauch shared his take on how AI will transform front-end engineering, while Runway’s CTO Anastasis Germanidis outlined his playbook for planning a roadmap at an AI startup amidst rapidly-evolving technology. 

Just as the breakneck pace of advancement kept founders on their toes, the quest to find product-market fit also became more urgent in 2023. Follow-on funding became more difficult to secure and the pressure to hit metrics and operate more efficiently started to sink in. To help steer builders staring down this seemingly insurmountable climb, we set out to collect stories from founders that cleared this hurdle with our recurring Paths to Product-Market series.

We sat down with remarkable founders like Laura Behrens Wu of Shippo, David Hsu of Retool, Bryant Chou of Webflow, and Christina Cacioppo of Vanta (along with over a dozen others) to get the unvarnished story of how they went from 0-1 and found what we’re calling extreme product-market fit. With present-day billion-dollar valuations, we pushed past those shiny, up-and-to-the-right company trajectories, and dug into all the false starts, blips and moments of sheer grit that powered these unicorns forward. 

Our hope is that these stories served you well in these past 12 months, regardless of whether you were looking for inspiration for your startup’s journey to product-market fit, advice on how to build product in a post-LLM world, or frameworks for handling the past year’s challenges (such as a guide doubling down on retention and customer success, a primer on M&A, or pointers on how to shift gears from a BigCo to a small startup).

With that in mind, we present our collection of little tactics, resonant reminders and operating principles to guide you in the following roundup of the 30 best pieces of advice we heard in the past year. Take them with you as we’re thrust forward into all that 2024 has ahead.

1. Hit refresh on your interview questions for manager candidates 

Spotting folks who can become high-impact leaders at your company is exceptionally challenging in an interview setting. While you can probe IC skills with a coding test or other function-specific take-home projects, unraveling all the nuances that go into managing people can be incredibly tricky — especially with just a narrow sliver of time with each candidate. 

So we put out a call to some of the sharpest folks in our network for their best interview questions for management positions and assembled their responses into a new can’t-miss guide for hiring managers. Our goal? Give interviewers a fresh slate of questions to lean on, rather than resorting to the same ho-hum questions like “How do you describe your management style?” or “How do you motivate your team?” It was clear folks were clamoring for a fresh set of interview questions — the article with the full list turned out to be our most-read of the year.

Here are a few highlights: 

Tell me about a time when you delved into significant detail and got your hands dirty. - Gokul Rajaram, product leader at DoorDash

Walk me through the most significant change you’ve made as a manager in response to feedback you’ve received about your leadership. - Russ Laraway, author of “When They Win, You Win”

What dashboard do you open up every morning? - Alex Kracov, co-founder and CEO of Dock

Who on your team would you be happy to work for? “We all know the popular maxims: ‘Hire people you would work for,’ or ‘A players hire A players, and B players hire C players.’ This question gets at whether or not a leader actually lives by those principles,” - Brie Wolfson, former marketing leader at Stripe and Figma

Tell me about a time when you influenced another team in the company that had a diametrically opposed point of view. - Ravi Mehta, CEO of Outpace

Why did you leave IC work? - Farhan Thawar, Head of Engineering at Shopify

What processes have you put in place to ensure that each person on your team has a clear idea of the team’s goals and their own role and responsibilities? - Liz Fosslien, Head of Storytelling for Team Anywhere at Atlassian

2. Set goals by trying to tell a story 

You can't copy-paste your bigger company frameworks when you join a small startup. But zero process isn't the answer either. Take goal-setting as an example. 

"Managing a large team is a very detail-oriented exercise. You’re looking at headcount and schedules on a long runway, and that’s impossible in a startup setting. But too many early-stage teams opt to skip over planning and goal-setting altogether," says James Everingham, who jumped from big to small when he moved from Meta to co-founding Lightspark.

To hit that target Goldilocks, just-right amount of process, borrow his concept of “management by narrative.” Don't drill straight down into specific KPIs and targets — start by trying to tell a story. "Begin with a thesis, such as ‘This is what we're going to do this year.’ Break that narrative up into chapters, almost like titles. The flow is, ‘First we're going to do this, then we're going to do this, and then by chapter three we’ll have done this, and chapter four is the end, where we have product-market fit and we're scaling,’” he says.

But here’s the key for an early-stage startup: "As we’re building our plans, we only focus on those first three months, that first chapter. So we break that down into monthly high-level goals, and that's what I hold the team accountable for,” he says. In other words, don’t try to get detailed for longer than a few weeks out. "At a startup, it’s almost assuredly wrong past that. All you can do is make sure everyone knows the story, the short-term outcomes you're looking for and that they're doing work that maps up to support that.”

I like to go through every single thing the team is doing and ask: If this one thing weren't done, would we not be able ship the product? And if the answer is, ‘No, it would still ship,’ then it's off the list.

3. Opinions come at a cost — spend wisely 

As a founder, you’ve built the company in your own vision — and in the early days, you have immense influence over every single facet. But as the company grows and you bring on more manpower, suddenly your influence starts to shrink. 

But far too often, rather than empowering these super-sharp folks who have been hired to make their own well-informed decisions, founders continue to make sure their opinions are heard loud and clear. But foisting your opinions on others can do immense damage to your workplace culture. Not only are you potentially wrong (because even founders and CEOs can error), but even if you’re right, it’s a risky move. 

At the helm of an entirely async company, Sidharth Kakkar, founder and CEO of Subscript, has had to carefully root out any of his own micromanagement instincts. He flags a couple of sneaky outcomes from being too free-wheeling with your opinions. 

Employees lose confidence in their skills. “You’ve squashed their creativity and you’ve squashed their ownership chops.”

Employees become more concerned with your opinion than finding the right solution. “You want to avoid folks thinking through problems like, ‘If I don’t do things Sidharth’s way, then that means he’s going to think less of me.’ Which is quite detrimental to the business.”

Employees become dependent on you to make decisions for them. “Then you condition folks to think, ‘I better just run all my decisions by Sidharth.’ And that is the worst possible outcome that you could imagine.”

No matter where you work or what role you’re in, you can use Kakkar’s advice to weed out your own micromanager tendencies: Before you give an opinion, ask yourself, “Am I right or do I just have an opinion? If I am right, what’s the cost of being right?” You might discover what you have to say is better off left unsaid.

Anytime you’re telling someone what to do you’re not actually solving the bug. You’re doing a really bad patch.

4. Balance the core product with new bets by looking to the horizons 

Once you find product-market fit the first time, a new challenge appears: How do you juggle improving your existing product with growing your business? You could maximize your core product, pouring resources into tinkering and perfecting it — yet, by doing so, you miss out on seizing new opportunities while competitors creep in. Or you could pursue innovative ideas at the risk of devaluing your revenue engine.

That’s why Shippo’s founder and CEO Laura Behrens Wu uses the Three Horizons framework to balance bigger product bets, as she explained in her Paths to Product-Market Fit installment.

Horizon One: Core product (70% resource allocation). “A Horizon One product is one that’s working really well and is the core part of your business, probably the majority of your revenue. It's all about optimizing Horizon One and making it work better and building this revenue engine. But you don't want to take too much risk here because it’s a more mature product.”

Horizon Two: Forward-looking products (20% resource allocation). “Horizon Two and Horizon Three products are forward-looking. You don't have product-market fit in those products just yet. Horizon Two is where you have a good hunch that there's something there, and it'll work.”

Horizon Three: Big risks (10% resource allocation). “Horizon Three products are insane ideas, and you're just dabbling. You have no idea whether they could be some business line in the future. A Horizon Three idea might mean playing around with how you can implement Generative AI into your product.”

Don’t get so obsessed with the big shiny stuff in the future that you forget about what is actually generating revenue today.

5. Pinpoint where you’re delivering feedback as a manager 

Folks are clamoring for more feedback from their managers. But when you ask these very same managers, there’s a disconnect — they feel they’re constantly delivering feedback. “The reality is that we’re never as explicit as we think we are,” says Marcel Weekes, VP of Engineering at Figma. 

So time and time again, Weekes has learned to cut closer to the quick. “As a manager, it’s almost painful to say, ‘I have some direct feedback from you.’ It may seem pedantic or, at some level, contrived,” he says. “So instead, we weave the feedback in among other things and now it’s watered down. It’s born from a place of trying to make people feel comfortable, but it has a very different effect — it makes people feel unsatisfied.”

It’s critical that we are very clear about positioning feedback as feedback. I want my direct reports to be able to leave the 1:1 and point to an exact sentence where they received feedback.

6. Walk confidently through two-way door decisions 

As a product leader at a growing company, the decisions you make only become more high-stakes as the organization scales. Each potential change to the product impacts a wider customer base, more voices across the org chime in with warnings of what could go wrong and the risk of failure looms larger. 

It’s only natural then, for product managers to take the path of least resistance. After all, a misstep could carry painful repercussions — for customers and users, for your team's momentum and for your career trajectory. 

However, playing it safe also carries a cost. Opportunities are missed, innovation gets left on the table — and possibly the biggest blow to scaling companies — progress can gradually grind to a halt. The key, Slack’s Chief Product Officer Noah Weiss says, is to find the right balance, fully evaluating risks while not becoming paralyzed by inaction. 

One useful framework for minding this balance is to think through decisions using the one-way vs. two-way door model: 

Two-way doors: “For example, it can feel very fraught when deciding on a new tagline for the homepage. It’s very prominent and visible. You can spend months internally debating and focus group testing, and still end up with an option that no one person wants to 100% claim. But, while visible, a new homepage tagline is an incredibly easy decision to reverse. This is an example of a two-way door. Teams should feel comfortable walking through this decision knowing that making any changes or updates to the tagline will be easy to revert.”  

One-way doors: These are decisions with long-term repercussions that are much harder to reverse. For example, changing the name of a core product. Once product leaders identify an upcoming decision as a one-way door, Weiss encourages giving yourself enough time to work through what the biggest risks are ahead of time, so you can be more judicious.

7. “Give away your people” and prepare for high performers to leave

The cold hard truth about working in scaling companies is that people, and in most cases, top performers, are going to leave. The question for managers shouldn’t be how to prevent this natural growing pain from happening, rather the focus should shift to: What are you doing to prepare for it? 

As a longtime startup operator and leader, Clarissa Shen saw so many well-meaning managers get caught off guard by superstars moving on, that it catalyzed her to craft a new philosophy: Managers should always be prepared to give away their people, and when the time comes for a high performer to leave, Shen argues that managers will actually be better off for it.

“One thing I learned early on was managers need to have very specific conversations with reports on what they are looking for in their next growth opportunities,” she says.

Accept that people are going to leave. Especially if you are a first-time manager, it’s much easier to go into the role accepting that someone is going to leave, rather than blaming yourself when it happens.

One of the simplest ways that managers can get ahead of the blindside is to regularly take a pulse check on their direct reports’ career goals — not just during annual performance reviews. Shen offers a few low-lift tactics on how managers can do this in their next 1:1s: 

Try making every fourth 1:1 a career growth conversation. Block off at least an hour of time, allowing for the conversation to meander 

Create a unique title for the meeting. It should be separate from a weekly 1:1 and a quarterly performance review 

Come prepared to talk about your own career growth and bring examples or stories of opportunities that you’ve spotted for yourself

8. Track your mood – not just your metrics  

To cope with the wild swings of uncertainty during the hunt for product-market fit, Productboard’s Hubert Palan came up with an interesting practice. Using a spreadsheet, he plotted how he felt about the prospects of the company three times a day: morning, lunchtime, and evening, and called it his “Founder Mood Meter.” 

“I measured my own happiness as a proxy for the customer's happiness. At first, it was completely up and down. Eventually, I started feeling much better about where we were headed once the feedback became consistently more positive. It became obvious that there was a real market here — not just a few nerdy tinkerers,” he says. 

And then, it happened. “We kept building the features, and eventually, the features became good enough for the jobs, and then suddenly, it was there: hockey-stick growth.”

9. Strip “and” out of all your headlines

Copyhackers' Joanna Wiebe serves up incredibly sharp copyrighting advice, so we were thrilled to feature her wisdom on The Review this past year. As she sees it, the word “and” is an insidious "lose-money" word. "It shows up everywhere. It’s small and functional, so it seems to be friendly. But our brains don’t enjoy trying to suspend a bunch of thoughts in the air as we seek meaning or try to decide. Every time you use the word 'and,' you lose a conversion. If you insist on using 'and,' then you need to be cool with losing leads."

For an example, read each of these headlines, pausing to close your eyes, count to ten, and then try to remember the key points covered. The first headline is the easier one to remember.

​​This is because of a concept called interference, which defines our inability to recall information when we’re exposed to more than one message at a time or otherwise distracted.

If we’re going to add words to the page — and risk losing a conversion each time — we’d better use words that are not going to double-down on interference. Any word on the page needs to earn its place.

10. Inject gratification to the grind of startup life 

As a psychologist working 1:1 with founders as they ride the waves of startup life (and a founder herself), Dr. Emily Anhalt has seen firsthand that founders have a remarkable ability to delay gratification — they are uniquely gifted at putting their heads down and pushing forward without much recognition. 

But eventually, that seemingly endless well of self-assurance and motivation will run dry. “It’s hard to push towards something in perpetuity if you don’t pause and feel proud of what you’ve accomplished thus far,” says Anhalt. (As she explained in her latest article with us, this isn’t the only founder trait that’s a double-edged sword.)

And this heads-down mindset that can slowly infect the rest of the team. “Founders who don’t believe they themselves deserve recognition for small wins will be less likely to recognize their team. They’re less likely to say good job, or celebrate milestones, like raising a Series A,” says Anhalt.

A mistake founders often make is assuming that because they need less validation along the way, no one on the team needs gratification either.

Anhalt shares advice for founders to tweak their approach to inject a dose of validation energy for themselves and mete out kudos to others.

Be your co-founder’s cheerleader. “It can be very lonely to not have your work recognized — but it’s also incredibly uncomfortable to toot your own horn. I recommend that co-founders shout each other out and share with the rest of the team what the other is doing. For example, I will make a point of saying to the team about my own co-founder, ‘Alexa has been working so hard behind the scenes to secure this next round. Here’s everything she’s been doing and it’s been so cool to see her in action.’ That way the rest of the team can share in that pride.”

Make the ask. “Founders are quick to ask for constructive feedback. But I recommend they also ask for positive feedback, too. Ask your team what they think you’re doing well or in what ways they feel supported. What kind of milestones can they not wait to get to? Why are they most excited to work at the company?”

Tell folks they’re making a difference. “There’s a lot of talk about ‘the trophy generation’ and that people just need constant compliments. But I believe it’s the meaning-making generation. Folks want to know what they’re doing actually matters. If not, why are they working so hard? It’s important to help your employees understand that their hard work is being seen and that it makes a difference to the company’s goal. While it’s important to let people know when they need to make a change, it’s also important to cheer when things are going well.”

11. Learn to be an emotional dampener as a manager 

After nearly a decade managing product teams at places like Webflow, Dropbox and Airbnb, seasoned product leader Jiaona Zhang encourages anyone eyeing the manager’s seat to carefully consider if motivating a team (and all the soft skills that come with it) is something you’d enjoy taking on. Taking on emotional labor to boost your team’s morale while also massaging their frustrations requires its own unique, nuanced touch.  

“An important skill set of being a good manager is what I call being an ‘emotional dampener’ for the team,” Zhang says. “An emotional dampener finds themselves in situations where they know their team is upset, they know people are frustrated about a certain problem but choose to coach them and help them by dampening their emotions as opposed to riling them up. If that’s not an easy role for you to take on, you should think twice about being a manager.”

There's a saying that a good manager is often a punching bag and a therapist. It’s important to go into the role with eyes wide open and be aware of all the emotional hats a good manager needs to wear.

12. Hire smarter with a capacity plan

Startups have developed a bit of an allergy to over-engineered processes. So when it comes to creating spreadsheets and building models that keep tabs on a company’s future headcount plan, leaders often write this off as unnecessary bureaucracy. But when the company starts to scale, you don’t want to fall behind because you neglected to take the time to do this important strategic work.

But Richard Cho, SVP of Talent Acquisition Charlie Health, has seen the dangers of what happens when businesses start to scale without a proper headcount plan in place.

“A typical headcount forecast starts in Q3, is finished in Q4, and is finalized in Q1,” Cho says. “This means that recruiting teams — who are sometimes the last to know when the final forecast is approved by the board — can’t start responding to that forecast until sometime in the middle of Q1, putting recruiting teams months behind before they even can post a job description.”

While starting to keep track of hiring data can feel intimidating, don’t worry about creating anything fancy here, says Cho. The important thing is to get your hiring funnel down on paper, so you can get into the habit of inputting and collecting data when it comes your way.

Here’s an example of what a bare-bones capacity plan can look like for an early-stage startup:

13. Figure out how much self-doubt you can absorb 

For Michael Grinich, the period between idea validation and product launch was unusually lengthy, as it was over a year before what became WorkOS made it into the hands of a single customer. But as any founder grinding away before launch can tell you, that extended time table allows for self-doubt to creep in the backdoor. 

A big part of having the grit to survive the startup process is this: How much doubt can you absorb? How long are you willing to be misunderstood? How long are you willing to be wrong, or think that you’re wrong, yet keep working on it anyway?

For other builders lost in the wilderness, he shares three reminders for not allowing self-doubt to knock you off course:

Know the difference between productive vs. unproductive self-doubt. “If you can make the concern concrete, if you can point out a specific reason why your idea is not working, that’s useful self-doubt. But if you can't really make it concrete, it's probably just anxiety or existential angst.”

It’s okay to seek occasional external validation. “Looking for bits of external validation is normal because you’re human. After we launched, we made this deck of all the positive tweets from people saying they’d love to use WorkOS. We just needed something to hold onto because we knew the feeling would evaporate in a month or two.”

Accept that self-doubt never goes away. “To this day, there's stuff that we're investing in and shipping that has very little concrete traction, but we have really high confidence that long term it's going to be extremely valuable for us to build. The things that you work on that could have huge upside all look like a big bet without much definition around the success or the ROI. But you just have to have this innate belief that it's going to work in some way.”

14. Identify your goal-setting philosophy

It’s time for your quarterly goal-setting exercise. But the new SVP, Julie, pushes back on setting an aggressive target for her team. She’s got some scar tissue — at past companies, if she sets a target and misses, it’s likely her budget that gets the chop next year. So instead of going big, she wants to opt for a modest target that she knows her team will over-perform.

While fictional, this example is all-too-real amongst executive teams, says COO advisor (and former PayPal BizOps leader) Amanda Schwartz Ramirez. “Most execs come into goal-setting with their own assumptions (and baggage). You can speak to four different leaders and you might get four different philosophies regarding what it means to achieve a goal. For example: 1. All goals need some margin for error (success = 70%). 2. Goals and plans are interchangeable – you either achieve, or you don’t (100% or bust). 3. Shoot for the moon! Land amongst the stars! (50% is a massive success). Or 4. Set modest targets and wildly outperform (150% is celebrated).”  

So, who’s right? Well — everyone (and no one). What matters most here is consistency across the team. So pick the goal-setting philosophy your company wants to aim for, publish it widely amongst the team to set those expectations, and stick with it. 

15. Stay paranoid on the hunt for PMF 

Many describe finding PMF like a lightning strike, an unmistakable “you’ll know it when you see it” type of feeling. But it was decidedly more ambiguous for David Hsu when he was building Retool.

“We talked to someone who said that finding product-market fit was so visceral that you immediately feel it — like a geyser exploding. We honestly never felt that. Every customer we got — whether that was number four or number fourteen — felt like the last customer we were ever going to find,” he says.

The wide range of use cases for the product compounded this feeling. “DoorDash was building logistics tools for drivers. Brex was building tools to manage credit limits. And that was totally different from what a tutoring company was using Retool for,” Hsu says. “So I remember wondering whether we would actually be able to serve these customers and make them happy with so many different use cases.”

It wasn’t until the 40 logo mark and the first few million in ARR that Hsu started to feel confident. That’s why he advises founders today to stay paranoid, and keep pushing. “It’s like rolling a stone up a hill — if you stop pushing, it'll start rolling back down rapidly.”

16. Don’t fumble the bag with bad deal room etiquette

Navigating acquisitions is one of the more underexplored topics in company building — yet it became especially relevant as market upheaval had some founders reconsidering their exit strategy. 

After selling three different startups successfully, Daniel Debow has become something of an expert on the art of M&A. His most recent startup Helpful, was acquired by Shopify in 2019 and he’s worked at the e-commerce company ever since as a VP of Product. On the side, he advises several founders in his former shoes.

While the intricacies of an acquisition are unique to each company’s situation and ideal outcomes, Debow has seen plenty of well-meaning founders fumble a good opportunity inside the boardroom.”  Here are the three mistakes would-be sellers should avoid if they want a deal to go through:

Don’t inflate your numbers. “Remember that these are people that are betting some portion of their careers on you. Appreciate that,” Debow says. “If there is something you are worried about, air that out early. You’re not going to fool them into buying you.” 

Don’t be arrogant. Debow sees this the most with founders using non-standard definitions for their numbers or performance, intended to make them look better. Remember, “they don’t have to pull the trigger,” says Debow.

Don’t think the deal is over just because they said no. “A great mentor of mine once said ‘all great deals are lost before they are won.’ If a deal falls apart, that might just be the moment where you have to rally. You can’t give up on this journey. You have to be quite relentless.”

17. Diagnose your customers’ problems like a doctor 

While toying with the idea of building a startup focused on mental health, Harry Ritter spoke to around 50 therapists to get a better sense of their challenges. We were most struck by how he leveraged his medical background here, bringing the precision of a physician attempting to diagnose a patient to the customer discovery interviews that informed his early vision for Alma.

In addition to asking each person he spoke with for introductions to three more therapists, Ritter created interview guides that standardized the conversation with the same 10 questions across the board to avoid introducing his own bias. “They were built on some of the interviewing skills that I had from medical school. When you're trying to diagnose someone, you're supposed to combine both narrow questions and open-ended questions.”

Narrow questions. These types of questions grant you a structured data set you can use to think about what comes next. For example, “What application are you using for finding new patients?”

Open-ended questions. These let you capture information you may not have thought to ask. One open-ended question Ritter asked was, “What are the biggest challenges that you face in your private practice today?” “The one consistent theme that I hadn't thought about was loneliness as solo providers,” he says. “Alma’s emphasis on community and connection really came out of that insight that I hadn’t expected going into those interviews.”

18. Carry storytelling into your sales pitch 

“Storytelling is one of the most powerful tools a seller has in their toolbelt. Why? Because stories elicit emotion, and most purchase decisions are driven by emotion,” says Emery Rosansky, First Round’s own VP of GTM.

We feel this sales/stories connection when we decide to purchase a new top because we like the way it makes us feel when we try it on for the first time. But for some reason, when it comes to software, folks (especially founders who haven’t come up in the sales org) tend to forget that emotions and storytelling are just as important to the startup selling process.

Whether it’s pitching to a potential investor or trying to close a deal with an early customer, one of the biggest mistakes Rosansky sees when she works with founders is folks rattling off quantitative numbers, with little (or any) time devoted to storytelling.

Is it more powerful to show a slide full of statistics on the impact your product has had across your customer base or to tell a story about a specific customer and how they went from struggling to scaling with your solution? If you said the latter, you’re right.

So look for natural opportunities to integrate storytelling into your discovery calls. “This can be the company origin story, stories about other customers who had similar challenges to the one your prospect is sharing, stories of customers who had similar objections to your product that the current prospect has (and how they overcame them) or stories of customers who ‘won’ using your product,” says Rosansky.

19. Find your co-founder ritual 

Maintaining a healthy co-founder relationship can feel like going through the motions of a delicate dance. The choreography only works if there is absolute trust between partners, and you must constantly anticipate the other person’s moves. If you don’t, the chances of you both stumbling are high. 

Labelbox’s Manu Sharma and Brian Rieger don’t take this task lightly, even five years into their co-founder relationship. As their company continues to grow, they’ve had to scale the processes that ensure their relationship stays intact and thriving alongside it. 

One of the simplest ways they’ve been able to remain on the same page is by enjoying a shared ritual. “We found that as the company scales, we spend less time looking at the same things or working on things adjacent to each other because it’s just a larger organization. So we intentionally spend many hours together on Friday every week,” Rieger says.

It’s uninterrupted time set aside for wide-ranging talks — the kind you can’t squeeze into your calendar in between back-to-back meetings. The pair worked with an executive coach to come up with a series of questions to make the most out of their shared Fridays. The first bucket of prompts is designed to evoke reflection about the company and themselves: 

What are your recent observations about the business?

What are the most important things we should be working on?

What is the biggest challenge you are seeing?

The second bucket was designed to create conversations around alignment: 

What are the big opportunities out there?

How is the market shifting?

What have we heard from our partners, customers, and advisors that we value?

“When you are in the soup, it’s a little hard to see the whole thing. These questions are designed to force you to step back and observe outside your own world, challenging the ongoing thoughts in your head that are often contextual and narrow,” says Rieger. 

20. Keep having customer conversations until you can predict what they’ll say next. 

Christina Cacioppo had a bit of a learning curve when it came to figuring out go-to-market for Vanta. “I had no selling experience whatsoever — the last thing I sold prior to starting Vanta was Girl Scout cookies.”

After exploring (and abandoning) several product ideas, customer conversations were her way through. “We decided we weren’t allowed to build anything at all. We had to just talk to people — and talk to them until we had a lot of confidence and a mental model of customers, their jobs, the problems they might have and how we might solve them,” she says.

Cacioppo’s advice here is to get into the details of their day-to-day life. “For discovery, the best thing we did was ask people to pull up their calendars. Then, we’d say, ‘Look at all the meetings you had in the past couple of weeks. What were the best parts of those past weeks? What were the worst parts? That finally got us to a problem worth solving.”

You’ll know you understand the problem when you can predict 75% of what a customer tells you.

21. Add “push the envelope” features to the roadmap 

In our series to unpack various companies’ journeys to product-market fit, one common thread has been those early-days decisions — the ones that seem small at the time but end up making an outsized impact.

Webflow co-founder Bryant Chou sat down with us earlier last year to dig into the company’s path to product-market fit, and this small observation stood out: “The most obvious things to build commercially are not the most obvious things to build from a product brand perspective,” he says. 

As a small example, one of the product’s earliest features was Webflow Interactions. The brainchild of their first employee (an engineer with a motion graphics design background), it aimed to give the platform the same level of digital authoring of video editing tools. Chou admits he didn’t really understand the importance of allowing designers to create a parallax scrolling or mouseover effect. 

But it turned out to be an inflection point that significantly elevated Webflow’s product brand among designers — and helped the company build momentum, with tens of thousands of signups after launching on HackerNews.

When I think about our product roadmap, I consider which features make commercial sense for us as a business, and which ones kind of pushed the envelope and make Webflow truly special — which aren't always the same thing.

22. Zero in on net dollar retention 

With a tricky macroeconomic environment stretching out sales cycles, this past year there was a renewed focus on shoring up existing customer relationships, not just amassing new ones.

So we asked several top customer success experts for their essential advice on bringing CS to the forefront. And when we asked them the most important metric to keep in mind during a downturn, we received a resounding chorus for one in particular: Net Dollar Retention. 

Calculated as a percentage reflecting revenue growth over time, measured by taking starting revenue, adding an expansion, and subtracting churn, NDR can offer perspective into why customer success is such a necessary function. 

Stripe’s Tim Smith explains why NDR tells a more holistic story than other popular CS metrics like churn. “Net Dollar Retention is a great construct for seeing the big picture around retention and renewals,” he says. “Churn is only a downside metric with the best possible outcome being zero churn, which will never happen even for the best product due to non-controllable factors. However, net retention is a more extensive metric that lets you include churn and expansion together. This puts your team in a growth mindset rather than focusing on downside potential.”

In times of uncertainty, customer retention, rather than acquisition, should be the primary focus. As adding new customers becomes increasingly challenging, your net dollar retention can save you.

23. Level up your strategy as you get more senior 

One risk when scaling organizations is letting strategy become a buzzword, rather than an action you see through. It’s a serious pitfall to avoid — a strong strategy marks the difference between a successful startup and a failing one. On top of leading top product teams, Jiaona Zhang also teaches product management at Stanford, so we’d be remiss if we didn’t include another gem from her on this list of advice. 

As she explains to her students, the hack to good strategy isn’t a robust Excel spreadsheet or a cost-benefit analysis comparing all the features in your roadmap. Rather, good strategy is good storytelling. 

“People tend to overcomplicate it, but it’s actually quite simple. Strategy is outlining the things you are going to do to get to where you need to go. I stress a lot around telling human stories,” says Zhang.

A good strategist should be able to say in 30 seconds what we’re doing for our users. 

As you widen the aperture and help your teams think strategically, Zhang reminds you to tailor your method to your audience.

“If you are working with a first-time PM, you are drawing a narrow box with a thick marker,” she says. “Inside the box, you are explaining the future we want to build. Outside is the goal we’re trying to achieve. As your team gets more senior, you no longer have to tell them, ‘this is exactly what you have to build.’ Instead, explaining strategic decisions turns into ‘I don't know what we’re going to build per se, but this is the outcome that we need to achieve.’”

24. Ditch your demo and replace it with a “marketing vignette” 

Instead of choosing one product idea and building a quick MVP, Material Security’s Abhishek Agrawal and Ryan Noon tested four different startup ideas by attempting to sell each of them — with no code, no demo, no prototype. 

They’d start the day with meeting an HR leader to pitch a people analytics product. The next hour, they’d go to a security person and pitch a security analytics product. And then, later in the day, they’d pitch another security product that was slightly different. “It was like a 9-to-5 job where we were trying to sell multiple different products at once,” they say.

Not only had the team not yet built a demo for any of these ideas, but they also didn’t even have a landing page or full mockups because they didn’t want to waste time on something they hadn’t yet validated. Enter “marketing vignettes.” These were pitch decks built to look like pared-down sales landing pages, with descriptions of different features. 

This tactic worked for a few reasons:

It gauged interest without overwhelming. “There was just enough UI to convey a concept without letting you get bogged down in it with a customer.”

It allowed the founders to experiment with messaging. “A big part of finding product-market fit early on is testing messaging. When you make slides, it lets you skip over product marketing because you're just thinking about bullet points that list features. But when you make marketing vignettes, you have to name your features and also convey in a couple sentences what the benefits are. It forces you to exercise muscles around positioning and marketing.”

It quickly helped the founders find out not just which ideas the customers cared about but also which ideas *they* were excited to pitch. “If you were struggling to pitch them, or if you were having to pump yourself up, it would become clear they weren’t winning ideas. But if you were energized by your own pitch, you knew you were onto something.”

See their real-life example in the image below, and read more of their tactics for finding product-market fit quickly here.

25. In a net-new role? Slow down to speed up 

“As a company’s first head of customer advocacy, I came in understanding that this would be a blank canvas that I would have to fill. I fell into a common trap, which is rushing in full speed,” says Kalina Bryant, a seasoned customer advocacy leader who’s held roles at Asana, Talkdesk, Anaplan, Marketo (and now advises First Round-backed companies).

“Often there’s pressure to show results immediately, to launch a customer advisory board or a brand-new program in a month. But you need to make sure you have the right people in the room — being wrong is very expensive, and not just in a dollar sense,” says Bryant. 

“You could be going after the wrong customers. You might not be sure what kind of feedback you’re looking for yet. You might not have a developed-enough roadmap to even show them. You can waste time by moving too fast. Outlining the customers and business goals you’re going after might take some time, but it sets the foundation for fast, creative experiments in the future.”

26. Lean into early founder-led sales — even for a PLG product 

Even though the Merge founders Shensi Ding and Gil Feig were big believers that inbound would be a powerful channel for the integration API product’s growth, the founders still dedicated immense amounts of time to outbound selling (in fact, they did all the sales conversations themselves for the first eight months). So why sink so many hours into talking to customers when leads were rolling in organically? “We still started with a lot of outbound because there’s no replacement for that learning. You just have to reach out to as many people as possible. Founder-led selling creates a tighter feedback loop that makes your product better,” says CEO Ding.

When you do founder-led sales you’re not just learning how to sell your product, you’re learning how to tell a story. This is essential to sell the vision to investors or to candidates you’re trying to hire.

The goal was to amass a ton of learnings that they could eventually pass over to their first head of sales hire. Here’s Ding’s summary of what worked and what didn’t:

What worked: Demoing. “What always pissed me off as an engineer was going into a vendor meeting and not being able to see the product. Once prospects could see how intuitive, yet powerful, our product was, they would be much more interested in using it themselves.”

What worked: Self-serve. Along similar lines, getting customer’s hands on the product sooner, rather than later, was key. “There was no barrier to entry to try out the product and validate that yes, Merge works. And then we can come in for a sales conversation to upgrade.”

What didn’t work: Meeting with the user. “We found that talking to certain personas didn’t get us closer to a sale. Meeting with an IC engineer or post-sales folks didn’t work — we needed to meet with someone with greater buying power, like a head of product or a head of engineering.”

27. Focus on problems, not solutions by finding the parking brake 

When bringing your product to market for the first time, it’s important to understand the difference between what your company makes, and what your company sells — because these aren’t necessarily the same things. 

It may seem like semantics, but excavating this difference will ultimately help founders understand the unique offering that sets their product apart in a crowded market, according to Jonah Berger, Wharton marketing professor and author of several business psychology books like “The Catalyst: How to Change Anyone’s Mind.”

“Too often leaders, salespeople or founders think they have a solution, regardless of what the problem is. They don’t know whether they’re truly selling a solution, and they also don’t understand which facets of their solution to focus on for a given audience, because they aren’t grasping that audience’s needs,” Berger says. 

“It’s not until you understand the problem that you can begin to prescribe the solution. Think about doctors. They don’t say, ‘Let me put a cast on your leg.’ They say, ‘Let me understand if the leg is broken and if it is, I can prescribe a solution.’”

Here are two techniques Berger suggests as guideposts for founders when trying to diagnose their customer’s problems: 

Think of the end result. Probe deeper into what you want to change by asking questions like “Whose mind or behavior are you trying to change? What are they doing now (i.e. the status quo) and what are you hoping they’ll do moving forward?” Then, take a beat to reflect on what you’ve tried already. “Ask yourself, How have you tried to change things, and what was the result?”

Find the parking brakes. It never hurts to try and look at things from another’s perspective. Rather than thinking about what you can do to create change, ask yourself why haven’t things changed already? What are the parking brakes that are stopping people?

28. Use community as a springboard for product development 

Deepica Mutyala, co-founder and CEO of the beauty brand Live Tinted, catapulted herself into the spotlight long before becoming a founder through a viral video she made demonstrating red lipstick as a color corrector for dark circles under her eyes. The video struck a chord, especially with South Asian women who historically felt underrepresented in the beauty industry, and Mutyala immediately built a community beauty page and started creating content catering to this group of people. 

And when the time came for Mutyala to start creating her own beauty product, she had a powerful, loyal base willing to give feedback and provide customer research.  

“Our community was always rooting for us,” she says. They were genuinely excited about our interest in product questions and became our biggest champions,” Mutyala says. “So when we shared the opportunity to test out a potential product, we had no shortage of volunteers.” 

In fact, there were so many volunteers that Mutyala ended up having to curate testing groups through a selection process, in order to make sure she had a diverse group. It was also an intimate process, full of mutual trust. 

“We invited volunteers to come to my house in LA to try out the product, test it, and make sure it worked for them,” Mutyala says. “While we’d post publicly asking our community for help on a project, we were never explicit about what we were building. Everything product-related was all behind the scenes.”

29. Understand where brand and performance marketing excel (and where they fall short) 

Between the two of them, Sarah Emmott and Holly Chen have led marketing teams at Atlassian, Google, Square, and Slack, as well as advised dozens of startups on their marketing strategy. And time and time again, they get questions thrown their way about whether companies should invest in brand or performance marketing.

This is a mistake, says the duo. A balanced combination of both brand and performance advertising can create a powerful marketing strategy that not only supercharges brand loyalty but drives immediate conversion. It's not about one being better than the other but recognizing when and how to use them effectively.

Here are a few of the differences between the two approaches:

To put these ideas into practice, they unpack these two ad examples from Square:

Square’s Forged in Flint from their “For Every Dream” film series are brand ads showcasing the emotional and inspirational stories of small business owners with no direct product value props. 

Meanwhile, Square’s Register performance ad puts the product value prop front-and-center using messaging and imagery optimized for viewers to consider or immediately try the product.

30. Skinny down your MVP

We’ve interviewed hundreds of founders and have heard about all the different ways to approach building an MVP — from launching and iterating rapidly, to focusing on “lovable” features, to not building one at all.

But Kubecost’s Webb Brown moved at a speed that we haven’t quite seen before. “We built an MVP literally over a weekend. It was built using another technology by the name of Grafana, which today is a really big observability platform. It had very little code written but was essentially a dashboard that could show you different Kubernetes cost trends and dimensions,” Brown says.

Along with the MVP, they published a Medium post to explain why they were launching this open-source project. In a matter of days, over 150 people had engaged with the “product.” This was enough of a positive signal for the co-founders to go out and start talking to potential users. “We were focused on answering questions like, what is the problem? Do people care? Are people willing to engage? We didn’t need 120 features to answer those. And sometimes that means being comfortable having a suboptimal solution for the sake of validating a hypothesis in the short term,” he says.

You need to have a clear idea of what you’re trying to prove, at that moment in time, to either de-risk the business or move the ball forward in a material way.

Top illustration by Alejandro Garcia Ibanez, featuring Kalina Bryant, David Hsu, Christina Cacioppo, Daniel Debow, Jiaona Zhang.

As the year draws to a close, you may find yourself in a reflective mood. There’s plenty to take stock of as you look back on how 2023 went. There’s the quantitative stats — if your startup hit its revenue goals and if your team delivered on its quarterly numbers, how your team grew (or shrank), or personal metrics like how many books you read or miles you racked up on Strava. 

But there are the fuzzier achievements to unpack — the things you got right, the mistakes you learned the most from, the relationships you deepened, and the “aha” moments you’re taking with you into the coming year. 

It’s the nature of fast-moving startups that there’s not much space to stop and reflect. Of course, bits and pieces might be covered during annual performance reviews — but depending on your company calendar, those rituals might not line up neatly with the end of the year, and they also have a different (and narrower) lens. 

Ultimately, a more holistic self-directed reflection exercise is well worth undertaking. Whether it’s how you spent your time, the morale of your team, the feedback you heard, or the direction of your career there are plenty of different yardsticks you can use to evaluate how you fared. And if you’re a resolution person, this can help you place the starting block for what you hope to achieve in the next 365. 

To that end, we’ve combed the Review archives for our favorite questions and contemplative exercises that will help you embark on a wide-ranging retro to set yourself up for success in the new year. 

WHAT PROJECT SHOULD I HAVE QUIT EARLIER? 

Quitting isn’t exactly a popular topic in startup circles. Instead, we reach for softer euphemisms, like “pivoting,” “iterating,” or “going in a different direction.”

Annie Duke (a former pro poker player, bestselling author and First Round’s Special Partner in Decision Science) has made it her mission to rehabilitate the word, which has been given the Voldemort treatment. “Success comes from sticking to the stuff that’s working and quitting the rest. That’s why quitting is a skill you need to get good at.”

It's true that in order to be successful at something, you have to stick to it — but that doesn't necessarily mean that sticking to something makes you successful.

As you look back on the past year, there are probably some projects that make you cringe a bit. Maybe they turned out to be complete failures, or they just took way longer than they should have. Whether it’s a new marketing experiment, a sales deal that just won’t close, a new direction with the product strategy, or a hire who isn’t working out, Duke doles out specific advice for reflecting on where things went awry this year and getting tactically better at quitting in 2024. 

“There are all sorts of benchmarks that you can set for yourself of what you need to see happen within a quarter within two or three quarters. Those benchmarks become what I call kill criteria, literally criteria for killing a project or changing your mind or cutting your losses. If you miss them, it means you’re going to quit,” she says.

Here’s a simple formula for developing your kill criteria: “If by [date], I have/haven’t [reached a particular state], I’ll quit.” 

You can apply this approach at every level of the company. Take this sales example: “Imagine that you are pursuing a sales lead that was generated through an RFP. It's six months later and you’ve lost the deal. Looking back, you realize there were early signals that you were not going to win. What were they?” says Duke. “Maybe you had a few meetings and they couldn't get a decision maker in the room. Maybe the RFP matched a competitor a little too closely. Maybe they just wanted to talk about pricing in the first meeting and didn’t even want a demo. They're probably trying just to use you as a stalking horse to beat somebody else down on price,” she says.

“When you’re actually in the situation it’s hard to see it.  When you’re in the middle of a deal, you continue to pursue it and insist that you can still win. Assembling the criteria in advance can help you see if it’s not a deal that’s worth pursuing actively or bringing it further into the funnel. You can have different levels, like automatic kills or ones where you need to seek out further information before making a decision,” says Duke.

SHOULD I REVAMP ANY OF MY REGULAR MEETINGS?

For better or worse, you probably spent a big chunk of the past year in meetings. Be honest here — how many of these were actually effective, and how many could have just been an email (to borrow a popular lament)? 

That’s not to completely bash meetings — a well-run meeting can be an incredibly effective tool for driving alignment and making quicker decisions. But this doesn’t happen by accident — great meetings are meticulously crafted.

“Executive meetings take up a big chunk of time and energy for everyone in the room. The last thing you need in the midst of all the other challenges of running and growing a business is for that meeting to become a bad recurring experience,” says Asana Head of Business and COO Anne Raimondi. 

So rather than rolling into the new year with the same slate of meetings with the exact same structure, consider creating a short survey to send to folks: 

When you leave the meeting, do you feel energized or do you feel drained?”

What’s your favorite part of the meeting?

What do you find most helpful?

What do you find least helpful or least productive?

If you could change one thing, what would you change?

Whether it’s coming up with crisper agendas and pre-reads, inviting in more cross-functional guest speakers, or firming up your approach to assigning deliverables and next steps, this simple survey can point you towards tangible steps that will move the needle.

And for your 1:1s with direct reports, try this idea from Mutiny CEO Jaleh Rezai for revamping your regular check-ins, dedicating one meeting a month to a higher altitude perspective. 

Most of our time at a startup is spent zoomed in. Monthly reflection is when we zoom out.

Once a month, she asks each of her direct reports to reflect on the three things that went well the past month, and the three things that they want to improve. To encourage transparency, Rezai also shares her own 3x3 exercise. (Grab her template to try it out yourself.)

And crucially, the dialogue always ends on a buoyant note: What are you most hopeful about as you think about the next month?

HAVE I BEEN USING MY TIME WISELY?

When it comes to startups, it’s easy to feel incredibly busy. There’s no shortage of tasks to tackle, and not nearly enough time (or people) to take them on. The real challenge to being truly productive is focusing on the right things. 

And there’s no truer test for if you’ve hit this mark by zeroing in on your calendar. Front’s founder and CEO Mathilde Collin recommends taking a step back to ask yourself the following questions:

Does your calendar actually reflect the priorities you’re orienting your team around every single week?

Is there an activity you aren’t spending enough time on?

Do you have the discipline and the built-in time to disconnect and step away?

To build this behavior in going forward, borrow her suggestion to make this calendar audit a weekly ritual. “I have a 15-minute ‘Review My Calendar’ slot every Friday afternoon. I revisit our quarterly goals and a few top-of-mind topics. I then look at my calendar for the upcoming week to make sure it matches up,” she says. “For example, if hiring is a big push, I need to spend about a third of my time interviewing executives. When I look at my calendar and it’s packed with product meetings or I only have one interview scheduled, then I know that I’m not doing enough to make progress, so I’ll add a sourcing session in.”

And if your whole week is completely booked up, that’s an important signal, too. Some projects (usually the most impactful ones) require deeper work, where you step back away from an endless slew of emails and pings, and dig into some of the thornier issues on your plate. Collin calls this her “stepping back time.” “It’s half a day each week where I allow myself only a notebook — no computer — to really concentrate on a key issue,” she says. 

If you’re looking to more deeply audit how you actually spent your time, we suggest this detailed manual from Levels co-founder and CEO Sam Corcos. (He’s another huge proponent of using your calendar as a single source of truth, and he diligently blocks his time rather than relying on an aspirational to-do list.) Along with an exacting analysis of how he spends his time, he also shared a helpful (simplified) version of the spreadsheet that he uses, which you can make a copy and use for yourself. (Corcos notes that if you want to back-fill with your existing calendar data, you can go into Google Calendar and download all your historic calendar data as a CSV, then upload it to Google Sheets. If you haven’t been keeping a rigorous calendar to date, you’re better off starting fresh and keeping the spreadsheet up to date in 2024.)

DO I KNOW WHAT’S MOST IMPORTANT TO MY BOSS IN THE UPCOMING YEAR? DOES MY TEAM? 

You came up with a new project or initiative, pushed it across the finish line, and hit the targets you set. But it didn’t seem to make much waves across the org and instead seems to come and go with a whisper— what gives?

You may have misread what your boss cares about most — and focused your precious time and energy on a nice-to-have, rather than a hair-on-fire problem. 

“The intersection of your success and your manager’s success is where magic happens, and where your opportunities for fulfilling impact lie,” says Julie Zhuo, co-founder of Sundial and former VP of Design at Facebook. But finding out what your manager cares about isn’t a one-and-done event at the start of a new quarter — it’s an ongoing exercise in alignment as the business shifts. And amidst the usual startup chaos, folks can lose sight of the bullseye. 

Often people are so focused on solving their own problems, they don’t think about how their proposed solutions create more problems one level up. What are your boss’s problems and how can you solve them? 

To get started with identifying this perfect overlap, try this simple idea from Davit Balagyozyan (software engineer at Stedi): “Write down every person you work with, their biggest need, and their most ideal ‘OMG this makes my life so much better!’ Now you have a list of your organization’s greatest needs and solutions. Now, decide if filling any of these needs aligns with you (Hint: If you’re excited about it, that’s usually the right mark)” he says.

This is of paramount importance for folks up and down the ladder. For those earlier in their career, it’s easy to default to looking for guidance from others on what you should be working on. Liz Fosslien (Head of Storytelling for Team Anywhere at Atlassian) encourages newer folks to make a habit to step back and ask yourself, “If I were running this company or team, what would I do? Where would I invest my time? What might I try that no one is currently working on?”

And for folks who are later in their career, managing their own teams, understanding what’s top of mind for higher-ups is essential to pointing the entire team in the right direction. Use these prompts as your guide: 

Is our work making an impact on my boss’s most important issues? 

How healthy and frequent is my communication with my boss? 

Am I showing enough visibility of the work my team is producing to the right people? 

Are we sharing our work at the highest level possible, at the earliest point possible and in a collaborative way? 

Are we getting honest and frequent feedback on that work? 

WHAT’S THE MOST IMPACTFUL PIECE OF FEEDBACK I GOT THIS YEAR? DID I GIVE CLEAR FEEDBACK AS A MANAGER? 

A steady stream of feedback is essential to becoming someone who people are excited to work with — and it’s a career accelerant. On the flip side, not getting this intel is a silent career killer. You get passed over for new roles or special assignments without ever understanding why, never getting an opportunity to develop and prove you can do better.

There’s all sorts of advice out there centered around getting better at giving feedback to others, but rarely is it focused on attracting useful feedback about ourselves — even though it’s in our own best interest to do so.

So if there’s not a particular piece of high-impact feedback that stands out from the past year, consider how you might flip the script in 2024 and become a feedback magnet. Here’s some advice from Arise founder and CEO Shivani Berry to empower the folks around you to share more: 

Narrow the question. Instead of asking vague questions like, "Do you have any feedback for me?" or "How can I improve?" ask specific questions to unearth truly constructive feedback. “How can this deliverable be 10% better?” or “Was I saying ‘like’ too much in that meeting?” are much more likely to elicit specific areas of improvement.

Swap “feedback” for “advice.” “Feedback” is a loaded term. Not only do you tighten up when you ask for “feedback,” so does the feedback giver. Swapping it out for “advice” is more inviting and indicates you value your colleague’s counsel. Instead of saying “Can I have some feedback on what I could have done better?” say “Do you have any advice on how I can improve on X?” You’ll achieve your goal of receiving constructive feedback, but the experience will feel more comfortable for the feedback giver.

Get people invested. Start by sharing your improvement areas with your team and ask them in advance for feedback as they see you in action. This will help call their attention to it and de-risk their fears around giving you feedback. For example, say to your colleague: “In our next 1:1, I’d love feedback on how well we’ve been collaborating so far,” or “After my All-Hands presentation, can you please give me feedback on my communication skills?”

When you share more specifics around how you’d like to grow and then follow up to close the loop, folks will root for your success more — and celebrate in your wins alongside you.

And for folks in a management role, take stock of how often you’ve delivered transformational feedback to folks on your team — and whether you’ve been explicit enough that it cuts through the noise. “As a manager, it’s almost painful to say, ‘I have some direct feedback from you.’ It may seem pedantic or, at some level, contrived,” says Marcel Weekes, VP of Engineering at Figma. “Instead, we weave the feedback in among other things and now it’s watered down. It’s born from a place of trying to make people feel comfortable, but it has a very different effect — it makes people feel unsatisfied.”

It’s critical that we are very clear about positioning feedback as feedback. I want my direct reports to be able to leave the 1:1 and point to an exact sentence where they received feedback.

Even when we deliver positive, reinforcing feedback, we often leave out the specifics.  “For example, if they nailed a sales call, instead of saying ‘Great job’ you can try something like, ‘Nice job on that call! I noticed that you built strong rapport with the client, made them feel heard, and diffused their concerns about the product.’ Now they have a better sense of what's working and what they can double down on in the future,” says Anita Hossain Choudhry, co-founder and CEO at The Grand. 

HOW HAS MY JOB CHANGED? 

The best (and sometimes the worst) thing about working at dynamic, fast-moving companies is that everything is always changing — the landscape, the product roadmap, what users want, your team, your manager. That means, what the company needs from you is always changing. But, because you are living it every day, it can be hard to detect even very material changes in your role and responsibilities over time. 

Your job shifting is like aging — hard to detect on the day-to-day scale, easy to detect on the decade scale, and fuzzy-ish in between. 

That’s why Brie Wolfson (who previously helped build Stripe Press and Figma for Education) recommends a semi-annual reflection exercise where you rewrite your own job description. It’s perhaps a bit unconventional, but it may peel back some unexpected insights. 

Start with the main three components of a typical job description: 

Overall description of the relationship between the role and the broader company and its goals (usually 1-2 paragraphs of prose)

List of responsibilities (usually bullets), and 

Skills that are required to do a great job. 

“I’ve found that 1 often remains relatively stable, 2 changes all the time, and 3 evolves steadily. Ideally, the responsibilities trend increasingly strategic and interesting to you over time and that 2 never outpaces 3,” says Wolfson.

Here’s a template you can use to construct your own JD: 

“I would suggest that the first paragraph has a very memorable one-liner mission statement. Think about what you would want your manager to say if someone asked her, ‘what is $NAME working on these days?’ Why? Because they probably do! And, you should probably have some language that you can consistently use to talk about your role with others, says Wolfson.

And if you see meaningful changes from version to version, it’s probably a good idea to check in with your manager. Depending on how you are feeling about your role and responsibilities, you can use this to gut-check and guide a conversation on your areas of focus. 

“Another thing I’ve been experimenting with is creating an aspirational job description for ~1-2 years out. This creates a clear, tangible articulation of where you want to go in the future. What you write doesn’t have to have any conception of your current skills or what the company needs. It’s all about you and where you want to go. You may find that this role exists, and that you can have it!” says Wolfson.

AM I READY TO MOVE ON?

As you look to the year ahead, many folks are gearing up for a job hunt, either due to layoffs, or stagnating in your current role.

For folks who are coming from the latter mindset, founder-turned-investor Ellen Chisa flags that a few different feelings might be popping up — nastiness, an unsettled stomach, FOMO, envy, or dread. Make sure these aren’t impatience in disguise, she cautions. Ask yourself these questions: 

Am I not learning new things? Is that my fault or my company’s fault?

Do I disagree with how my co-workers are doing things? If yes, have I truly tried to change their minds?

Do I trust the leadership here?

Do I feel blocked, and if so, why do those roadblocks exist?

Have I given myself enough time to adjust? To learn? To find the right advocates/mentors/teachers/allies?

Is it just that the honeymoon has worn off and the real job has started?

When you start feeling unhappy in your work, you owe it to yourself to get specific about changes you could make for it to get better, and to develop your own innovative solutions and experiments to try. Before jumping ship, Liz Fosslien suggests three places to get started with leveling up your current role: 

Find stretch job postings. “These are roles a couple of levels above where you currently are that excite you, and then look at the listed requirements. What skills would you need to build to be competitive? Which sound particularly fun to you? Then, bring your new list of growth opportunities to your next 1:1 with your manager or volunteer for projects that would offer you relevant experiences.”

Listen to those pangs of jealousy. Too often, we perform all kinds of mental gymnastics to convince ourselves we're not envious of someone else. Instead, try to pinpoint exactly what it is you covet, and then ask: Can I take classes to acquire that skill? Should I take on different kinds of projects?

Look into your network. Think about four people’s careers, then ask yourself: Whose career am I most envious of?” she says. “Break down their career path: What’s the first step you could take to bring yourself closer to what you envy?” When you’re struck with career envy, don’t push it down — observe it. What does that other person have that you wish you had? What steps can you take in that direction, to become a version of yourself that you’d be jealous of?

But if you run through these exercises and keep finding yourself looking for the exit door, it might in fact be time to move on. Molly Graham (a former exec at Google, Facebook, Quip and Lambda School), suggests starting with these four lists: 

• Things I love doing
• Things I’m exceptional at
• Things I hate doing
• Things I’m bad at

“The best version of your career is finding jobs that are in the Venn diagram between what you love doing and what you’re exceptional at. This may sound obvious, but oftentimes as you get more senior, the Venn diagram is often ‘things I’m exceptional at’ overlapping with ‘things I hate doing.’ You have to know yourself well enough to turn those jobs down, even when someone offers you the super sexy role full of things you hate doing. It’s a role that will bring out the worst in you,” says Graham. 

If you can’t immediately come up with items to fill each of these four lists, use these prompts as your guide which will, in turn, lead you to a more fulfilling next role: 

What were my favorite things that I did this last quarter?

What moments or weeks did I feel at my best?

When did I feel like I could keep doing the same set of things over and over again and be happy? 

When did I feel drained or depleted?

When did I feel bored? 

At what moments did I feel like my worst self? 

WRAPPING UP: LOOK TO MENTORS ALL AROUND YOU.

As you look to the year ahead, it may seem overwhelming to try to make tangible improvements in all these different areas. This is where you can lean on mentors — to encourage you, gently nudge you to be better, or point to an unexpected solution. But when folks talk about mentorship, they tend to sketch it out with a specific set of parameters. It’s a defined, 1:1 relationship between someone more senior and someone more junior. The mentor is the keeper of all sorts of wisdom — from functional expertise, to management advice, career trajectory, and everything in between. 

Instead, consider that mentors come in all shapes and sizes, and they’re all around you. Identify the superpowers of the folks you work with (even more junior folks), and how you might best learn from them. Someone might be a remarkably productive person, with expert tracking docs that you admire. Another might run a sharp, effective meeting, or is a whiz with an analytics dashboard. Rather than looking to one single mentor who excels at all the different areas in which you’d like to grow, find bits and pieces from the folks you work with each day, both up and down the org chart. 

So as you consider your own areas of self-improvement in 2024, try this simple framing from Raylene Yung’s career advice for engineers as your guide: How can I be as good at [X] as [this person]? 

It was the middle of 2020, and it became clear to Slack’s Chief Product Officer Noah Desai Weiss that the product’s first-day user experience needed a complete overhaul.

Up until this point, the product team had tinkered with hundreds of little experiments to the core platform’s UI — all trying to inch towards optimizing the onboarding funnel for new teams signing up. But amidst all of the experimenting, Slack’s growth had plateaued.

“It was sort of like climbing a mountain range,” Weiss says. “We had reached the top of a small hill, but we knew that there were other bigger hills just out of sight. So we took a giant step back, and looked around to see what the rest of the terrain was.”

Staring down an onboarding funnel that wasn’t ramping as many new users up as they’d hoped, Weiss made the pivotal decision to do an entire overhaul of the first-day user experience. “We called it Project Day One. Everything from the moment a user landed on the website or the mobile app, through creating an account, onboarding the first few teammates, and starting an initial conversation was ripped up from the ground and scrapped.”

It was a huge swing — one that could have landed with a decisive thud. But it did exactly what Weiss had hoped, a new burst of energy to beat stagnant growth. “It took us to the top of a new hill and brought us higher up than ever before. It allowed us to see that there was still a lot more that we can climb.”

And it’s the type of gutsy call that has made Weiss one of the foremost product experts. Throughout his seven-year tenure at Slack, he’s run several parts of the product business — leading everything from new product features like Huddles and Clips to running the self-service SMB business. Before Slack, he led the product team at Foursquare, scaling the pre-revenue company from 3 million users to over 50 million, bringing in $35 million in revenue.

In this exclusive interview, he opens up the decision-making playbook he’s relied on as a product leader at Google (leading the structured data team), Foursquare, and now at Slack. His goal? Help product folks take bigger, bolder bets with product decisions — ones that will bring in outsized returns, not just incremental shifts.

He starts by sharing his contrarian takes on two popular pieces of product strategy advice. Then, he walks us through the three-step process he uses to operationalize quality decision-making. (Spoiler alert: it boils down to sharing context, building trust and factoring in risk.) He wraps by zooming out and sharing how Slack’s product team thinks about making big bets, sharing two tactical ways to embed calculated risk into your product roadmap.

Judgment and intuition may seem like squishier skills that aren’t easily honed. But these decision-making principles apply to folks up and down the ladder, from an entry-level PM to a senior product leader. With Weiss’s tested frameworks to guide you, taking big swings will start to feel more routine and familiar, rather than daunting and insurmountable.

Hot Take #1: You can’t experiment your way out of every product problem

So much of decision-making comes down to what informs your choices — our outputs are only as strong as the inputs we are given. Weiss breaks down product inputs into two schools of thought: quantitative and qualitative. Ask any product leader which they favor, and chances are they lean towards letting the numbers talk. But Weiss feels taking the latter approach has some underrated merits.

“One of the things that we talk a lot about at Slack, which is very much in contrast to my early days at Google, is about not being data-driven with every decision that you make,” Weiss says. “Data can help solve easy problems, but it doesn’t actually solve the hard problems.”

A hard problem, he says, can’t be solved by experimenting your way out of it. “You have to figure out if it’s a big swing you want to take. You do that by using intuition.”

The distinction Weiss makes here is that the solutions to meaty, strategic problems product leaders face can be data-informed, but shouldn’t rely solely on data as a crutch.

It’s become fashionable to say that everything can be empirically answered by data. The ethos, especially in product, is unless you are doing everything as an experiment, then you are doing it wrong. And I disagree with that.

So when it comes to mapping this back to his own product decision-making process, Weiss likes to start any project by asking three questions:

• 1. What is the problem we are trying to solve for customers?
• 2. Why do we think this approach would help them?
• 3. What impact do we expect this to have? Whether measurable or immeasurable.

When you reach the third and final question, that is when to decide whether you can run some tests and experiments or if you have to learn about it through other means, he says.

“An unhealthy approach that you sometimes see with growth teams is this addiction to the velocity of experimentation,” he says. “Growth teams stop thinking about ‘the why’ behind what you’re doing and start focusing more on experimenting without thought. The hope is that you end up in a better place than where you started.”

That’s not to say there is no room for experimentation on a product team — quite the opposite. But Weiss argues that a strategic product leader knows the difference between when to experiment on something, rather than running tests willy-nilly.

“Certain types of product features are more conducive to experimentation, like when you are making isolated changes. A good example of this is A/B testing a checkout page, where you are trying to consolidate time to checkout from four steps to two steps. That's a great place where you can empirically answer does this change increase the conversion rate?”

But for many other types of change, and definitely for most early products, product leaders don't even have the scale or the time to run a test that gets statistical significance. “In those cases, you have to use intuition, judgment and strategy a lot more,” says Weiss

For larger, bolder features (like Slack’s new day-one interface) decisions should be taste-driven. “For decisions that hinge on what our customers love, we’ll always consult the data, but gut checks and strategy steer those bigger, bolder ship decisions.”

Hot Take #2: Focus on your own hand, not the whole card table

Let’s say you’ve sat down for a game of poker. What are you focusing on more — the hand you have in front of you, or the outcome of the whole table? If you picked the latter, you aren’t alone. Poker champion (and First Round’s Special Partner in Decision Science) Annie Duke dedicates a whole section in her bestselling book “Thinking in Bets” to this line of thinking. It’s called resulting — and it can be costly.

Weiss counts himself as a fan of Duke’s frameworks, and this one in particular. “She explains that if you look at how a hand played out, as opposed to how you played the hand, you can take away lots of really bad lessons on how to play poker. Because even if you happen to take the whole pot, you might be missing that you just got really lucky when the final cards hit the table, and that doesn’t serve you well for next time.”

Resulting can also be applied to quality product decision-making. “You can still use the outcomes of your decisions over time in aggregate as a signal, but trying to evaluate yourself or a team based on a single outcome at a single point in time is likely going to draw a lot of spurious conclusions,” he says.

An alternative approach is to get comfortable making smaller changes in increments over time. “If we go back to our mountain metaphor, oftentimes product leaders are staring down their next summit with little to no visibility,” Weiss says. “Have trust that the incremental decisions you make over a longer period will provide more valuable learning lessons to inform each decision you make going forward.”

It’s easy to get swept up in a grand vision, but realistically you can’t deploy a feature and get five years’ worth of feedback and learnings in an instant. How will you know what will resonate with customers? How do you know what the market will react to?

How to operationalize for quality product decisions: The startup leader’s playbook

Product leaders have to make tough calls, often without any real data or historical precedents to rely on as guideposts. But there is a way product leaders can think about operationalizing their decision-making process, and a lot of wisdom can be borrowed from how product is run at early-stage startups, Weiss says.

“At these places where there are only ten, 20, or 30 people at the company, it’s hard to even know whether you are making quality decisions because you may not even have a product on the market,” he says. “But on the flip side, the reasons that make startups feel so risky also enable them to be excellent grounds for decision making.”

He breaks down the three bedrocks of quality decision-making, explaining how early-stage startups get this right and how to keep up the pace as your product team scales.

1. Share context

“Almost always, when I look at a team or project at a larger org trying to make a decision with differences in opinions, the root of those differences almost always starts with shared context,” Weiss says. “Or lack thereof.”

The first step to identifying if your team is lacking shared context is to ask yourself a series of questions, Weiss says. “Does everyone making the decision have the same knowledge and information? Is everyone using the same backdrop to weigh the pros and cons fairly?”

In Weiss’s experience, the answer is more often than not a resounding no. “Alignment is the fundamental challenge with almost every large company,” he says. “Communication is hard, and people are just busy. But if you can crack the code and keep your organization aligned and focused, it’s like a superpower for velocity.”

• What startups get right here: “There is a tremendous amount of shared context that a smaller group has in every direction about the mission, the strategy, the customer, or what they are trying to achieve,” Weiss says. “That context becomes a shared language used when they are trying to make decisions.”

Be transparent, and then hit repeat.

The two fundamental practices to start cracking this code are transparency and repetition, according to Weiss.

On the transparency front, making information widely available for every person weighing in on a decision is crucial to making sure product teams are inputting a chorus of different voices and avoiding blind spots.

“Leaders can do this by simply sharing everything they possibly can with their teammates and those directly involved with the decision at hand,” says Weiss. “But the real kicker here is repetition. Keep grounding back in the context that matters most for the decision you are making, because people tend to need reminders,” he says.

Assume that if you don’t talk about something after a month, people will have forgotten about it by then. Alignment isn’t static. You don’t get to do it just once.

2. Build trust

Maintaining and preserving shared context is only one piece of the puzzle. Product leaders often find themselves charged with gathering consensus from teams across the organization — often with a level of healthy pushback. “In order to do this well, you have to have a decisive point of view, yourself,” Weiss says.

• What startups get right here: “At early-stage companies, there’s usually a high degree of trust. And with that trust, folks wind up pushing each other’s thinking more. There’s an expectation that you can push on ideas and not come across as threatening.”

If there’s no trust, it’s really hard for there to be conflict. And healthy conflict is necessary to get to any great resolution.

When a decision goes well, no doubt there is glory to whoever’s name is attached to an idea. But it’s that sliver of ownership that Weiss says rattles so many talented startup leaders into even attaching their name to something in the first place.

“Nobody wants to be attributed to a bad decision,” Weiss says. “No one wants to stick their neck out there, even if they were going off the inputs they had at the time. If it suddenly turns out to be a disaster, no one wants to be at fault. People become paralyzed with fear, and then you have a consensus-driven approach because no one wants to take ownership.”

Relying too much on consensus-driven decisions is the biggest mistake Weiss sees in product teams at scaling companies.

When you are guided by consensus, it often means you are reaching the most vanilla or neutral outcomes.

To inject some startup-level trust into your org at a larger team, Weiss says the best way to do this is to practice consistency. “Repetition is the best strategy you can use to build trust,” Weiss says. “My old board members at a previous company used to say, ‘The best leaders say what they are going to do, do what they said or let you know why doing it wasn’t possible.’ You’ll know you’ve built that trust when your team feels their expectations are met after you announce a decision.”

It doesn’t especially matter what product leaders are sharing with their teams, but Weiss says it matters more that reports know the information they are receiving is transparent .“By exercising this transparency over and over again, it’s possible to build trust with folks across your organization in a scalable way.”

Another transparency technique Weiss recommends for product leaders is to borrow from their engineering counterparts and set up a blameless post-mortem at your next team meeting. The main idea here is to shift the blame from an individual when an outcome goes haywire to being an organizational failure instead.

You want to avoid a culture where people become petrified of having high convictions and feeling the blame when the results of their ideas don’t work out as planned.

Building this type of culture must be intentional, according to Weiss. “This doesn’t stop just at post-mortem meetings. You need to have a culture where you’re not putting individual blame when outcomes go wrong. On any individual decision, optimize for the pace of learning and the impact will follow.”

3. Factor in risk

As a product leader at a growing company, the decisions you make only become more high-stakes. Each potential product or feature change impacts a wider customer base, more voices chime in with warnings of what could go wrong, and the risk of failure looms larger.

It's only natural then, for potential negative consequences to give you pause. After all, a misstep could carry painful repercussions — for customers and users, for your team's momentum, and for your own career trajectory. This inclination towards risk aversion is understandable, says Weiss.

However, playing it safe also carries a cost. Opportunities are missed, innovation gets left on the table, and — possibly the biggest blow to scaling companies — progress can gradually grind to a halt. The key, Weiss says, is finding the right balance, fully evaluating risks while not becoming paralyzed into inaction, and operating with enough confidence to move forward decisively.

• What startups get right here: Early-stage startups are inherently risky — and taking big swings comes with the territory. After all, there aren’t too many wholly safe bets when you’re building from 0-1. On high-performing startup teams, this risk is acknowledged, rather than an emergency break to pull that grinds projects to a halt.

One-way vs. two-way door decisions

A key skill for any seasoned product leader is knowing which choices warrant careful scrutiny and which don't require sweating the small stuff. Not all decisions carry equal weight.

One useful framework Weiss offers for thinking through decisions is Amazon’s “one-way” vs “two-way door” model. By splitting potential choices into "one-way doors" and "two-way doors,” Amazon founder Jeff Bezos was able to dial up his decision-making pace to an electric speed. Weiss is a big fan of this framework and even had his team adopt the philosophy. Here’s how he breaks it down:

• Two-way doors: “For example, it can feel very fraught when deciding on a new tagline for the homepage. It’s very prominent and visible. Thus, you can spend months internally debating and focus group testing, and still end up with an option that no one person wants to 100% claim. But, while visible, a new homepage tagline is an incredibly easy decision to reverse. This is an example of a two-way door. Teams should feel comfortable walking through this decision knowing that making any changes or updates to the tagline will be easy to revert.”
• One-way doors: These are decisions that are much harder to reverse. “These have long-term repercussions and are hard to de-risk,” says Weiss. For example, changing the name of a core product. Once product leaders identify an upcoming decision as a one-way door, Weiss encourages giving yourself enough time to work through what the biggest risks are ahead of time, so you can be more judicious.

We have this saying at Slack that you should walk confidently through two-way door decisions. Which is to say, don’t be paralyzed by things that are easily reversible.

The more two-way door decisions product leaders can identify, the faster they can move. But Weiss adds one last thing to consider when making speed a habit. “You want to make sure that all your teams know that most of the decisions you are going to make are two-way doors, and set the expectation that these will be made with a faster pace,” Weiss says. “By making a distinction between the types of decisions that come across your desk, this will afford you trust from your team when you do need to move slowly on a one-way door decision.”

Diversify your risk with the 70:20:10 product roadmap rule

Now with frameworks in place to make speedy decisions with conviction, Weiss encourages product leaders to also consider the potential each decision has to change their business. He singles out another common problem of scaling orgs that are likely inhibiting bigger bet-taking.

“The inclination that’s developed over time for product orgs is to have a localized team that’s focused on a subset of the feature space, and you have one or two KPIs to meet,” he says. “And in any given quarter, success for the product leader and the team is incrementally moving that KPI you are directly responsible for.”

When Slack’s product leaders sit down to review their team’s roadmaps, diversification is key. “We look at the portfolio and make sure no two teams have the same exact mix of the type of goals they are working on,” he says.

Reviewing product roadmaps from this lens also allows the product team to examine if goals along the roadmap are taking big enough swings. Here, Weiss leans on the 70:20:10 model that he picked up from his time at Google.

They are tentpole products now, but there was a time when Gmail and Google Maps fell into that 20% category, Weiss says. “The logic was to keep investing in those bets even though they weren’t fully at scale yet. And the 10% category was around self-driving cars and AI.”

Even if you don’t yet have a multi-product suite, these same principles of balancing big bets with low-hanging fruit can still be applied. “Just be deliberate about what your allocation looks like and how it’s changing over time,” Weiss says.

Wrapping Up: Don’t write off the power of well-defined values

The process, depth and quality of a decision can be measured and mulled over ad nauseam, but ultimately, without an organizational culture that promotes autonomy and risk-taking, all of these frameworks become moot, according to Weiss.

“Slack actually created a product principle called take bigger, bolder bets. Which sounds like an obvious guiding statement for a product team, but the reality of working as one person inside a 1000+ person product development team is there are a lot of laws of gravity as an organization that prohibits you from doing so,” says Weiss.

Outside of the product team, Weiss points to Slack’s company-wide value of humility as a big motivator in the choices he makes every day. “When we unpack what humility means, it means being introspective. Being comfortable being self-critical. Not just as an individual but as an organization. Our company has always been pretty good at being self-critical and not assuming the momentum from the past year is guaranteed to continue forever in the future,” Weiss says. “Without being self-flagellating, we can still be self-critical. And I believe that having this awareness is where our biggest turning points came from.”

This article is a lightly edited summary of our podcast episode with Weiss. You can listen to the full episode here.

Eng folks — does this sound familiar? A high-performing engineer on the team moves into a management role (often with a not-so-gentle nudge from leadership). After all, the team is growing quickly, and someone needs to take the helm. Who better than someone who’s already proven their technical chops?

But, by Marcel Weekes’ estimation, at least half the time those newly-minted engineering managers will leave their post, retreating back to the IC sphere. “If this was the failure rate of a service, we would do a postmortem on it and be concerned that the failure rate was so high. But in this case, we tend to just shrug it off and say, ‘Engineering management wasn’t for them.’ We don’t dig in further,” he laments.

Even some of the highest-performing orgs can fall victim to this common tripwire. As the VP of Engineering at Figma (and previous VP of Eng at Slack) Weekes has risen in the ranks from EM to Director to VP. Along the way, he’s seen plenty of well-meaning engineering managers falter, and he’s on a mission to change the narrative.

“One of my goals is for us as an industry to better support people who are making the transition from IC to EM and get to a much higher success rate — because we need exceptional engineering managers.”

Before we dive into his playbook, let’s first start with his definition of exceptional people management: having different tools in your toolbelt, and knowing when to use them.

Exceptional managers know how to deal with situational differences. They don't bring a single hammer to every problem in front of them. They assess the situation and then they look to their toolkit — or go find new tools — in order to motivate and support that individual.

“A nuance that’s often glossed over is that when you're managing a team, you are both managing a group of people and the dynamics that come with that, but also individuals on the team. You may have senior tech leads on the team, junior people, someone who's going through a tough time personally, someone who's disengaged right now, or someone who's learning a new tech stack. And each one of those requires a different level of expectation, support, and encouragement,” says Weekes.

In this exclusive interview with Weekes, he unpacks some of the key reasons why the IC-to-manager transition is particularly fraught for engineers. Next, he shares tips crafted for startup leaders and new managers to dodge each of these common potholes. While Weekes’ advice is tuned towards the engineering side of the dial, there are plenty of pointers that will resonate with folks across the org chart. Let’s dive in.

WHY IS ENGINEERING MANAGEMENT SO HARD TO GET RIGHT? COMMON POTHOLES & SUGGESTED DETOURS

Problem #1: The best-suited folks aren’t being elevated to management.

Whether the company is opening up a net-new management role or backfilling an existing one, often the first place to start before posting on LinkedIn is looking within the walls of the company. And what better place to begin the search than the senior engineering folks who are consistently your top performers? Their code is crisp, their technical knowledge is deep. They will surely chart the right course for the rest of the team to follow.

It’s an understandable instinct, admits Weekes. “There’s some pragmatism around being able to hold a high technical bar for the rest of the team and effectively short-circuit technical decisions that the rest of the team may be making — getting to the right answer as quickly as possible,” he says.

But this ignores the fact that there’s a vast sea of differences between technical skill and people leadership.

If you ask world-class, top 1% engineering managers where they would’ve ranked themselves as an engineer, they’ll almost universally say that they were pretty good software engineers, but not great.

That’s not to say that there’s no advantage to up-leveling folks who are already intimately familiar with your tech stack and have subject-matter expertise about your product — but it shouldn’t be the only criterion. Not only will these technical wizards be increasingly dissatisfied as their calendars book up and they move further and further away from the code base, but they also may not have the wider array of management skills needed to excel in the role.

“An exceptional manager excels across multiple axes. The simplest definition is they make their team a lot more effective — and there’s so much that goes into that. They ensure their team has all the resources it needs to predictably deliver high-quality work. They’re a great recruiter and retain top talent. They’re adept at building cross-functional relationships with their design and product counterparts. And they give their teams very clear direction on what’s most important to the business,” says Weekes.

Solution: Comb through motivations, not just pedigree.

So rather than starting by evaluating the prospective manager’s code commits, begin with motivations — are they more energized by solving people problems or technical problems?

“If someone gets the most energy from solving really thorny technical challenges, you want to support them in going down that tech lead path. But if someone gets the most energy from helping a group of people do something they couldn’t have done separately, then that’s someone who has the right motivation to go into a management role,” says Weekes.

How do you use this barometer if the engineer hasn’t been in a people management role before? Look for opportunities where they might have tested the management waters. “If they’re at the point in their career where they’re being considered for a management role, they've probably had some level of interaction with a summer intern or with a new college grad who's been hired onto the team. Dig in here — ask how that experience went, what did they enjoy about it, what did they not enjoy about it, and what would they do differently the next time?” says Weekes.

“If you get someone who’s fairly reflective about helping onboard or up-level someone and their contributions to the process, then you have an engineer who is showing signs of wanting to move towards a people-oriented role.”

And a team member who rattles off a list of frustrations with the summer intern is a red flag. “Someone who doesn’t take much accountability in terms of what they could have done differently, or didn’t feel rewarded by the process, that’s an initial sign that this is not a role that would be motivating to them.”

Problem #2: New managers fall into a spiral that never pulls them out of IC work.

Particularly at startups, which are growing at a fast and furious clip, adding in a new manager class is often done somewhat under duress. A team isn’t moving as quickly as they used to — they’re missing deadlines, and prioritization seems to be a mess. It’s time to bring in some extra management support. “The way this often plays out is that someone who’s an IC on a high-performing team will be asked to be the manager because it’s growing quickly and the team needs additional support – and probably has needed it for a while,” says Weekes.

Oftentimes you’ll go from being a high-performing individual contributor on Friday to being a manager of 4-5 people on Monday, without much structure or support around you.

“Suddenly, people find themselves doing a new job that they haven't been trained for, don't necessarily have the skills for, and the company isn’t at the stage where it’s put together any formal training to help get them up to speed,” he says.

Enter what he ominously terms the “new manager death spiral.” “The team might start to fall a bit behind on a deadline. And the manager, who had been one of the highest-performing folks on the team, jumps in to help unblock. So they return to what they know best, and think that by writing code they can help the team get out of a ditch,” says Weekes.

Before you know it, you’re back to where you started. “At this point, the team is back to not having a full-time manager because that person is stretched so thin — they’re partly trying to manage, and partly trying to be an individual contributor. And they’re not doing either one all that well.”

To make matters worse, Weekes finds that engineering teams tend to face an extra burden here. “Within your typical startup EDP org, the bulk of the staffing is on the engineering front. So you end up with a situation where most first-time design managers or product managers or other functions might move into supporting one or two or three people initially. But for engineering managers, the first time they make that transition from IC, they’re often jumping into a team that’s five or six — maybe even eight people.”

Solution: Set new managers up with a bit of extra cushion.

Folks typically associate manager training with week-long snooze-worthy seminars and awkward role-playing exercises. While your startup may not be at the point where it has a robust, HR-led manager training program you’d see at a 60K employee company, that’s no excuse to throw folks into open water without a buoy to keep them afloat.

So try something lower-lift but still effective: setting new managers up with a management mentor. “I want to leverage the experience of the folks around me so I don’t have to make those same mistakes. It’s a super accelerant to someone’s evolution as a manager to learn from other managers who have tread the path before,” says Weekes.

If you don't have a learning structure in place, you're just asking new managers to make every mistake themselves for the first time.

“You need someone who you can talk to about, for example, the right way to approach a difficult performance review conversation. Literally just having that discussion with someone who’s done it before makes you 10x more effective the first time you do it,” says Weekes. “Without that, it can feel really lonely as a manager because you don't have a peer cohort or a group of people you can rely on. We’re just making it unnecessarily difficult for folks.”

New managers shouldn’t have to clear every single management hurdle all on their own — so pair folks with a mentor who can share their own hard-won wisdom and advice. “Having a growth mindset is important — but we shouldn’t be putting folks into a heightened stressful situation every single week without the right support around them. That’s a recipe for someone self-selecting out of the management path. Give them a sounding board.”

Here’s an example of one of his own hard-won bits of management advice that Weekes imparts on newer managers for one of the most common tripwires: doling out feedback. “When you ask folks what they’d like more from their manager, the answer is almost always they want more feedback. I read it in just about every performance review of a manager that I cover.”

But when you talk to managers, there’s a disconnect — they feel they’re constantly delivering feedback. “My hot take here is that when managers gear up to deliver feedback, they may think about it in the shower that day. They write it down and prepare to very deftly deliver it in a 1:1. But the person receiving it does not think that they got feedback or that it was constructive or actionable,” says Weekes. “The reality is that we’re never as explicit as we think we are.”

So time and time again, Weekes has learned to cut closer to the quick. “As a manager, it’s almost painful to say, ‘I have some direct feedback from you.’ It may seem pedantic or, at some level, contrived,” he says.

It’s critical that we are very clear about positioning feedback as feedback. I want my direct reports to be able to leave the 1:1 and point to an exact sentence where they received feedback.

“I think one of the major reasons managers don’t get this explicit is because hearing the phrase ‘I have some feedback for you’ causes some folks to get defensive right away. So instead, we weave the feedback in among other things and now it’s watered down. It’s born from a place of trying to make people feel comfortable, but it has a very different effect — it makes people feel unsatisfied.”

It’s a snippet of advice he’s shared over and over again with newer engineering managers he mentors. “Once people have done this a few times, it becomes much more comfortable. But there’s a huge activation energy to doing it the first time. New managers should recognize they're not in this by themselves. There are people you can lean on to help you through that first pass of doing your first difficult conversation of type X or Y.”

Problem #3: Managing former peers can be just plain awkward.

Let’s go back to the example that Weekes sketched out for us early on — you go from being a high-performer on the team, working closely with your peers to ship code, bash bugs and hit your deadlines. Suddenly, the switch flips, and these folks you were in the trenches with just yesterday are now the direct reports you’re supposed to be leading. You’re now the one setting the deadlines, maintaining a high bar and providing constructive feedback.

Let’s face it — it can get awkward, fast.

“I always advise people in those situations to recognize that the awkwardness does exist and that both parties are aware of it. It's not something that's just in the back of your head — it is actually a thing. And as with most relationships, it's best if you actually talk about that openly upfront,” says Weekes.

And don’t necessarily view managing former peers as a hindrance to your leadership growth. “One of the first things to do if you're managing a team of people new to you is invest a lot of time building those relationships. If you've already got those relationships, it may require some adjustment in terms of how you interact with folks, but at least you're starting from a strong foundation.”

And in many cases, the transition from folks viewing their former peer as a manager might be more seamless than you think. “In my experience, it actually feels most different for the person who stepped into that management role. When this is done well, that leadership has been signaled to the team for a while, even when that person was still an IC. They recognized this person as a de facto leader. In the past as peers, they might have gone out for coffee to ask for help on something. Now they’re getting feedback in a performance review. It’s a different venue, the stakes feel very different, but at its core, it’s the same type of communication.”

Solution: Don’t shy away from setting expectations.

One of the trickiest bits for new managers (especially folks managing their former peers) to get right is around expectation-setting — but this is perhaps one of the most paramount. “An effective manager is going to set a high bar in terms of what the expectation is. There’s a strong appetite for members of every team to know what is expected of them and how best they can help,” he says.

Every business is in some type of challenge. They're trying to grow, expand, survive — and everyone on the team gets up every day and they want to contribute to that success. But we need to know what the expectations are in order to deliver on those outcomes.

“When you're talking to new managers, this can feel like a totally different muscle. You're being really explicit with people who maybe were your peers not that long ago: ‘Here's what I need you to do,’ or ‘Here's what is expected of you.’”

Weekes advises a three-step process for getting it right:

• Step One: Set the rules of the road. “In the first couple of 1:1s start putting together a written document. How does the report like to receive feedback? Are there things that trigger them? What are the things they want to do more of? What are their ambitions? Where do they feel they need to be pushed?” says Weekes. “Whether it's someone who is your former peer and your friend, or someone who you just met, that helps set the table for how this relationship will go. Invest the time upfront.”
• Step Two: Open up the lines of communication. When it comes to setting expectations — for example, assigning a deadline for an upcoming project — always make it a two-way dialogue. “Ask your team: ‘Is this an aggressive but reasonable goal? Is this something we can land?’ And it almost doesn't matter if the answer is yes or no, because what you're doing is opening up the space to have a further dialogue about it and dig in more. There should be a healthy tension with how much you want the team to stretch — if you're hitting your goals 80% or 90% of the time, in my estimation, that's probably too much. It's probably the case that you've not set them aggressively enough. And it's really important that managers have a direct conversation with their team because it's not going to be the last time that you're setting expectations and you'll want to get sort of more aligned every time you do it,” says Weekes.
• Step Three: Evaluate success by being a reporter. With the expectations set, the guidelines are in place to evaluate the team’s performance. Weekes has a particular approach here. “This is something that feels very different to new managers. I try to encourage them to look at this not as judging people, but rather as being the reporter of facts and presenting a mirror to people so that they can see how they executed. Provide as much fact-based evidence as you can to people about how they performed relative to expectations, and also be really clear about what the next set of expectations are.”

One last bit of advice Weekes imparts to new managers when it comes to setting expectations — allow space for bottoms-up exploration. “The best goal setting is around setting the right metrics to track, and then empowering the team to figure out the right levers to pull. It isn’t leadership telling the team, ‘This is how to do it.’ It’s leadership telling the team, ‘This is what's important and this is how you'll measure it. How you get there is within your purview.’”

When teams feel like they’re ticket-takers and follow a specific directive of how to build out a feature, you see it in the way the product is built. But if you localize the decision-making and feedback loop at the team level, knowing that you're aligned with the outcomes, you can iterate much more quickly.

WRAPPING UP: DON’T LET PROMO TRACKS GET FOLKS INTO MANAGEMENT FOR THE “WRONG REASONS”

To borrow a reality dating show trope, are folks venturing down the management path for the right or the wrong reasons? “That may not even be on them,” reminds Weekes. “It may be the structure of the company they operate within. In order to get a pay increase or to be recognized and valued by the company, they need to be on the management track.”

And so, despite being much more at home with their noise-canceling headphones on coding away uninterrupted, folks agree to take on a management role with their sights set on a pay bump and greater influence. Top of the list of these new manager complaints? Their calendar looks wildly different.

One of the biggest things that a lot of first-time managers talk about is losing control of their own calendar. All of a sudden, your day-to-day is run by a calendar instead of pull requests or feature tickets.

“Oftentimes as an IC you've got a couple meetings a day and you can slot in blocks of time where you get to do heads-down coding and cranking on the work that you really enjoy doing. But as a manager, meetings are the currency of the realm. You spend a lot of time as an information broker, getting information, disseminating information, making decisions — and that happens in meetings,” says Weekes.

So be very candid with folks considering the manager path about the challenges of the role and what they’re giving up — it might just save the whole team a world of headaches. “Ultimately, management is a hard job and not without challenges. So if you get into it for the wrong reasons and you’re not motivated by the problems you need to solve, the difficulty of the job will increase exponentially.”

To go back to the kernel of the problem here, folks (often rightly) assume that in order to grow their influence and their career at a company, their value is measured in their number of direct reports. As a company, it’s vital to carve out career tracks for folks who want to be deep-diving ICs and technical subject matter experts, without devoting their time to solving people problems. So, for starters, consider how you’re rewarding people on each track, with ladder rungs and promotion tracks that don’t rely on building out a team.

And disseminate decision-making across the team — not just concentrated (and thus, bottlenecked) at the engineering manager level. “You want the manager setting up the frameworks and processes and the environment in which people can make decisions as close to the problem as possible. And in that case, you’ll have senior engineers across the board making decisions,” says Weekes.

That doesn’t mean these decisions happen without review. “But a high-performing technical leader (not just a people leader) can be providing that review layer as well. Chances are, they will be more engaged and happy in their role if they aren’t dealing with some of the things that they consider the ‘people manager tax.’"

When Laura Behrens Wu landed in San Francisco for the first time in 2013, it was just for the summer—or so she thought at the time. By the time her fintech startup internship ended and she was slated to return to Switzerland to complete her MBA, she couldn’t bring herself to leave.

Thrust into the fast-paced environment of a team of 20, she had become enamored with startup culture. She reveled in the power she had been given, even as an intern, to do things like pitch ideas directly to the CEO and take on meaningful tasks to help the company prepare to raise venture capital.

“It was truly a magical moment for me,” says Behrens Wu, who was accustomed to a far different work culture back in her home country. “In Germany, straight out of college, jobs are pretty hierarchical. You start at the bottom of the ladder and don’t get any real responsibilities.”

Unsure of what to do next, she met with Simon Kreuz, a fellow German grad student she knew from college. He, too, was in San Francisco. And he, too, did not want to leave. So, they thought, why not start a business together?

“Honestly, there was some personal desperation around wanting to stay in San Francisco,” she says. “We like it here so much. We didn’t want to go back to Europe. We wanted to stay and make something work.”

So the duo quit their MBA program and founded what would eventually become Shippo, a billion-dollar software platform that powers shipping for the likes of Shopify and Wix.

But before Shippo was the leading multi-carrier shipping platform for more than 100,000 brands worldwide, it was a humble online store that sold handbags. What led to this drastic change in direction? Let’s track Shippo’s journey from idea to finding product-market fit (three times and counting).

EXPLORING IDEAS

The Shippo story begins in the fall of 2013 with two business school dropouts from Germany convinced that starting a business is their golden ticket to staying in The Golden City.

“The problem was we didn't have any groundbreaking ideas,” Behrens Wu says. “At some point, Simon and I decided to just start building something, and the easiest place to start was e-commerce.” With Shopify and Stripe smoothing the path to selling online for small businesses, it seemed like an easy enough entry point into entrepreneurship.

The Original Idea: An Online Marketplace for Independent Designers

The first thing the co-founding duo built was a Shopify store that was supposed to be a marketplace showcasing independent designers. But kickstarting a brand new marketplace was challenging. To get over the initial inertia, they decided to create demand by buying a few items from designers and selling them themselves.

After nabbing a few early orders, the founders were introduced to the ultra-complex world of shipping. First, they had to get the items they bought delivered to them from emerging designers. Then, they had to ship those items outbound to their customers, not to mention figure out how to manage inventory.

“Shipping was the least fun part of that experience,” says Behrens Wu. “It involved figuring out USPS hours, standing in line at the post office and trying to get the cheapest rates. There was no good resource for getting advice and no technology interface that was up to par with the other e-commerce technologies we were using for other aspects of running the business, such as Stripe and Shopify.”

At the time, online sellers basically had two ways to compare shipping options: go to the post office or navigate the individual websites of each of the carriers.

Behrens Wu and Kreuz knew there had to be a better way. Stripe and Twilio had already figured out how to integrate seamlessly with e-commerce platforms to enable native payments processing and communications, respectively. Why hadn’t anyone figured it out for shipping?

An Unexpected Pivot: Solving Shipping for SMBs

“We started talking to a few other e-commerce store owners to learn how they were shipping and see if they had any insights to share,” says Behrens Wu.

Initially, we were just trying to ship better ourselves. But through some early conversations, we realized that other people were having similar challenges, and that's how the idea for Shippo was born.

The founders had stumbled upon a bigger problem worth solving, but neither wanted to commit too early. Kreuz, for one, wasn’t sure he wanted to work on a logistics issue for the next ten years. And neither of them came from a shipping background.

“We were learning as we were building,” Behrens Wu says. “So we agreed to just build, get some customers and if we developed a passion for shipping along the way, we'd go all in.”

PROTOTYPING AND EARLY TRACTION

When looking for inspiration for a solution to build, the first product that came to mind was Expedia. “We thought shipping an order and booking a flight should be pretty similar,” says Behrens Wu. “You want to compare different rates, and then pick one option and buy it. We wanted to create a way to buy labels from different shipping providers all on the same website without having to go to multiple platforms.”

So that was their initial prototype: a search engine for buying shipping labels.

“Then we realized that, actually, a lot of our SMB customers ship many orders a month, not just one or two. And if you ship many orders (like on a daily basis), clicking through this interface one by one was too tedious and time-consuming,” she says.

Going back to the drawing board, Behrens Wu and Kreuz looked to the payment processing platform Stripe. “The Stripe model is API first, and we thought that model could work for the shipping industry as well. So we pivoted to that approach — which we're still doing today.”

But there were a few bumps along the way. “When we started talking to customers back then, we realized that shipping is such a mission-critical infrastructure component that if a company was big enough to know how to integrate an API, they didn’t want to integrate our API that was unproven and unused by anyone else.”

To get around the lack of usage and brand awareness, the founders decided to build a dashboard on top of the API and connect that to the Shopify App Store, which was fairly new at the time. Doing so gave their product more exposure and made it accessible to small businesses, whose owners likely didn’t know how to integrate an API.

By riding the wave of the Shopify App Store’s rising popularity, Shippo gained its first customers. Tracking signups plus shipping labels bought through Shippo, the founders were thrilled to see the coveted hockey stick growth chart. “The numbers were small in comparison to where we are right now, but seeing that chart was incredible. It showed us that we were onto something, and this was working,” she says.

Reflecting back on Shippo’s early traction, Behrens Wu acknowledges that market timing had a lot to do with it.

“We would have found a way to make it work through another platform or another app store, but the timing of the Shopify App Store and more people selling online really contributed to our early success,” she says. “Shopify was starting to take off, and there weren’t many shipping competitors on that app store. A lot of the customers we were talking to were already Shopify customers, and they wanted an easy way for them to be able to ship their orders. So we built this app and got a good amount of app store reviews, which then turned into word of mouth. That's how Shippo really started taking off.”

Then, in February 2014, Shippo got into batch eight of the accelerator 500 Startups, opening the founders up to a network of mentors, bootcamps and seed funding.

“That’s when things started feeling real,” she says.

People were starting to use the name of the company, Shippo. When it’s just the two of you talking about your startup, it sounds like it's all made up and not real. But suddenly, you have other people using the name, and it feels real.

Raising Money

In September 2014, after the accelerator program, Shippo raised a seed round of $2 million from 11 investors, including 500 Startups. But despite their accelerator pedigree, on the path to nabbing their seed round, Behrens Wu and Kreuz got rejected exactly 114 times.

Here are a first-time founder’s tips for fundraising:

• Stay in touch with those who reject you. “During our seed round, I met Albert Wenger from Union Square Ventures, who wouldn't invest at that point, but we really hit it off otherwise,” says Behrens Wu. “I decided to stay in touch with him, and every now and then, Albert responded to my emails. I kept him updated on Shippo’s progress, and he ended up doing our Series A. It was somewhat similar for our Series B: We met an investor during the A who then did the B.”
• All it takes is that first anchor investor to trigger a snowball effect. “When we started getting traction with a few investors who were actually in, everyone else followed suit really fast. But getting to the first one or two anchor investors—that was the hard part,” she says.
• Once you get that first investor, you can create FOMO in the others. “To get investors to commit, we told them, ‘We're fundraising now. We're starting to talk to other people, and other people are going to be interested, too.’ That was the forcing function for Albert to start looking more seriously at investing in Shippo. For fundraising, the founder needs to drive the demand.”

You need to create a FOMO situation where you can tell investors that other people are going to be making a decision in the next week or so to force that decision-making. Otherwise, investors keep wanting to see data points and updates over a long amount of time.

Behrens Wu and Kreuz knew it was time to raise a Series A when their customers started using the Shippo API directly. “The story we had been telling investors all along was that we had an API-first business but built a web app on top of the API, which a lot of SMBs were using. When we finally started getting adoption for our API product, it accelerated our growth because an API customer tends to be a larger customer than a web app customer.”

The founders geared up for a Series A and were almost ready to close when disaster struck.

“One of our largest customers churned,” says Behrens Wu. “We didn't know about the nuances and best practices of account management just yet because our previous customers were all SMBs. We eventually got them back, but that delayed our fundraising timeline. So yes, we learned a valuable lesson about account management, won this customer back and that customer is still a Shippo customer today.”

With the crisis averted, the founders went on to raise a $7 million Series A in September 2016 and channeled those funds toward hiring a team that could promote Shippo’s rapid growth and scale.

SCALING UP AND CONTINUOUSLY FINDING PRODUCT-MARKET FIT

There’s a reason we created an entire series on paths to product-market fit: so few companies actually achieve this crucial stepping stone to success. But for those that do reach their first PMF moment, it might come as a surprise that this milestone is really only the beginning. In order to scale up, you have to find product-market fit in new customer segments.

Nowhere is this more apparent than in the Shippo story. Astonishingly, the startup has found product-market fit three times and is on its way to a fourth.

People think you find product-market fit once and then you're good. In our experience, you find product-market fit for one customer segment or for one product, and then you need to continuously find product-market fit for new products that you launch or for new customer segments that you're entering into.

First PMF: Shopify Web app for SMBs

“Our first product-market fit was really narrow: for an SMB audience using Shopify,” Behrens Wu says. “And that gave us an awesome hockey stick chart. To this day, our SMB product through different app stores is still a solid revenue-generating engine for Shippo.”

Second PMF: API for midmarket companies

“We were always meant to be an API-first business, so that’s what we expanded into next. We had to ask ourselves, ‘How do we make this API work?’ The first objection we got from customers about using the API was that no one else was using it. But we started getting volume coming through the dashboard that was built on top of the API and were able to show that, actually, this API was already powering shipping for this amount of labels. From there, we started getting some API customers. The API customers that we’re serving now are mid-market customers, and we’re continuously pushing upmarket.”

Third PMF: Platforms and marketplaces that work with SMBs

“We're able to go to these platforms and marketplaces — such as Etsy, Depop and Mercari — and say that we know the SMB audience because we already have product-market fit there. And now we're going to help them build shipping for that audience that we know so well. A lot of SMB platforms and marketplaces use us for shipping in the background. We got to product-market fit there because they have the same customer segment that we already have product-market fit in: small and midsize businesses,” Behrens Wu says.

Fourth (upcoming) PMF in 2024: API for enterprises

“We’ve been doing a 2024 planning exercise to go further upmarket, where we're seeking product-market fit in that segment for the first time. We’re interviewing mid-market customers, learning from them and seeing what features we need to add to be more compelling in that customer segment.”

THREE HORIZONS FRAMEWORK: HOW TO BALANCE YOUR CORE PRODUCT WITH NEW BETS

Once you find product-market fit the first time, a new challenge appears: How do you juggle improving your existing product with growing your business? You could maximize your core product, pouring resources into tinkering and perfecting it — yet, by doing so, you miss out on seizing new opportunities while competitors creep in. Or you could pursue innovative ideas at the risk of devaluing your revenue engine.

That’s why Behrens Wu uses the Three Horizons Framework to work on both aspects concurrently while maximizing growth.

• Horizon One: Core product. “A Horizon One product is one that’s working really well and is the core part of your business, probably the majority of your revenue,” explains Behrens Wu. “For us, that’s our web app for SMBs. In the Horizons Framework, it's all about optimizing Horizon One and making it work better and building this revenue engine. But you don't want to take too much risk here because it’s a more mature product.”
• Horizon Two: Forward-looking products. “Horizon Two and Horizon Three products are forward-looking. You don't have product-market fit in those products just yet. Horizon Two is where you have a good hunch that there's something there, and it'll work. For Shippo’s Horizon Two, we're building a shipping optimization product and a billing and reconciliation product. Those are more of the forward-looking things we’re exploring.”
• Horizon Three: Big risks. “Horizon Three products are insane ideas, and you're just dabbling. You have no idea whether they could be some business line in the future. A Horizon Three idea might mean playing around with how you can implement Generative AI into your product,” says Behrens Wu.

70-20-10 Rule

But how is that reflected in resource allocation? The Horizons Framework suggests that the majority of your team members should be working on the Horizon One product, says Behrens Wu. “So you have, let's say, 70% doing Horizon One, 20% doing Horizon Two and then 10% playing around with Horizon Three.”

Don’t get so obsessed with the big shiny stuff in the future that you forget about what is actually generating revenue today.

Where Founders Go Wrong

“The mistake a lot of founders make is that they get so excited about Horizon Two and Three because those are the innovative, forward-looking things, that they neglect Horizon One,” says Behrens Wu. “Then the organization gets distracted and lets its foot off the gas on Horizon One, and you start getting deflated there. But to be able to enter Horizon Two and Three, you need to have Horizon One work well and drive a whole lot of revenue.”

From the founder’s seat, Behrens Wu focuses most of her time on Horizons Two and Three, but she’s careful not to let the rest of the organization follow her lead. “It's important for me to work on and be in the weeds on those forward-thinking projects because we're seeking product-market fit in those areas right now. I’m sending outbound emails myself and pitching customers for feedback.”

But for the rest of her team, she ensures they understand that their work on Horizon One is crucial for keeping the company running. “When we talk at all hands, we give shout-outs in the company, and we don’t just call out the big shiny things that are forward-looking. We make sure we’re talking about our revenue engine and praising that part of the business.”

When to Start Thinking About Horizons Two and Three (and When It’s Too Late)

In the earliest days of building a startup, Horizons Two and Three are just teeny-tiny specs in the atmosphere — you’re laser-focused on just getting Horizon One to work. But when is it the right time to start bringing Two and Three further into focus?

It’s probably earlier than you think, says Behrens Wu. As soon as you find product-market fit with your first product, start thinking about how to scale up. And while you scale up, think about other things you can build that are more forward-looking.

“It doesn’t need to be an entire pivot or an entire new customer segment or entirely new product,” says Behrens Wu. “It can be other features that you're adding to your existing product for future growth. Ideally, you start investing in Horizon Two and Three when Horizon One is still growing very well. When Horizon One is starting to flatten, I think it's a little too late. You should still do it, but it's a little too late to be optimal.”

HOW TO USE INDUSTRY OUTSIDER STATUS AS AN ADVANTAGE

Looking back, there were a lot of reasons why Shippo may not have worked. Chiefly, conventional startup wisdom might have said that while they had a great idea, the founders didn’t have the industry expertise to pull it off. As Behrens Wu admits, they had no business trying to build a shipping company.

People are so concerned with founder-market fit, but Simon and I for sure had no founder-market fit. This was our first time doing e-commerce and shipping — we were coming at it from a complete outsider's perspective.

But instead of seeing their inexperience as a disadvantage, the Shippo founders harnessed it as a strength. It meant that they, a small business, would be able to approach their target audience (e-commerce SMBs) from a shared perspective. They didn’t try to create any optical illusions that made the tiny startup seem bigger than it was — they completely pulled back the curtain.

“When the two of us would take phone calls or respond to customer requests, we’d be very upfront about being an SMB ourselves,” she says. “We weren't pretending to be a big company full of customer support people or product people. That made a difference in those conversations because people were willing to give us their time. And then the same people we built that relationship with were then also willing to leave reviews on the Shopify App Store.”

Behrens Wu and Kreuz leveraged their unconventional way of problem-solving when they encountered one of their first barriers to entry as an SMB merchant.

“When you want to ship as an SMB, you have to sign up for a FedEx account or USPS account. But in order to qualify for any kind of volume-based discount, you need to first build up volume, and that just takes time. Our thought was that anyone, as soon as they sign up for Shippo, should be able to start shipping right away. It's such a bummer if you need to go sign up for a USPS account and then come back to Shippo’s platform. It’s a subpar experience,” Behrens Wu says.

But getting these shipping providers to buy into the Shippo vision was difficult.

“We had to hack it a little. We first worked with a third-party aggregator that had a special kind of contract that allowed us to do this. Then, as we got enough volume, we started approaching the shipping providers directly and got our own favorable contracts for our customers.”

When you come at it from an industry outsider's perspective, you're able to think outside of the box. You're able to think about how it should be, not how it's always been.

Today, Shippo partners with 40+ carriers, including USPS, FedEx and UPS. “It's been a huge business development effort. Just this year, we got FedEx to agree to a new kind of account structure. So it’s taken us eight to nine years with certain shipping providers to get them comfortable with that and to bring that SMB- or merchant-friendly mindset to shipping providers.”

THE PATH FORWARD

It’s been ten years since Behrens Wu first fell for SF, a city she now calls home. But it’s no longer a desperation to stay in the Bay that drives her forward. Today, as a Series E startup last valued at $1 billion, Shippo is undeniably a success. With total funding of $154.3 million and more than 100,000 customers, there’s plenty more mileage ahead.

In 2023, Shippo delivered two major wins: In a one-of-a-kind agreement, it became the first shipping company to get a FedEx platform account, and it launched Shipping Elements, making it easy for e-commerce platforms like Wix to offer shipping capabilities natively. The latter is driving the company's continued move upmarket as it powers the shipping backends of major platforms and marketplaces.

Tracking the path of Behrens Wu from grad school dropout to unicorn startup founder, one thing is clear: She is a master at spotting the difference between chasing a dead end and simply being rerouted. In the course of getting her MBA, she changed directions to pursue starting a business instead of finishing a degree. On the way to building an online store, she and her co-founder discovered a much bigger problem to solve and pursued simplifying shipping instead of selling handbags. She struck the right balance between being doggedly committed to a vision and being open to an alternate way of achieving it. And the only way to stumble into those insights is to start moving in a direction — any direction.

“My advice to founders is to start building. Get something in front of the customer, and keep an open mind for how your initial product might evolve over time,” she says. “If customer feedback takes you in a different direction, going with it now carries way less risk than it would later. It becomes more costly when you have an organization and employees relying on you. But if it's just you and the co-founder right now, exploring a few different things is the right thing to do.”

Page the calendar back to 2013, and the world of tech looks quite a bit different. Slack had only just launched in a select preview release. Twitter (when we could still call it that) debuted on the public markets and Google released the prototype of its highly-touted (yet ultimately ill-fated) Google Glass product. Candy Crush Saga was Apple’s most downloaded app of the year, beating out mega-popular Vine (which was also released that year) for the top slot.

And while it may not have snagged the biggest headlines that year, around here we’re partial to something else that launched back in 2013 — First Round Review. Trends come and go in the startup ecosystem, but this little experiment that we launched a decade ago proved to have staying power. Ten years on, we’ve got nearly 600 articles, millions of pageviews, and hundreds of thousands of newsletter subscribers to prove it — and we’ve even spun off The Review format to the airwaves with 100+ episodes of our In Depth podcast.

We made a few promises to our readers back in 2013 when we launched The Review, which deserves revisiting as we celebrate crossing the decade mark this month:

• We'll get out of the way and let experts speak directly to you about what they believe is most important.
• Every article will serve up tactics that you can use today to change your company and your career.
• We will never be boring. The stories you find on here are crafted to teach, to engage and to stick.

These marching orders have taken us in all sorts of different directions over the past decade. There have been fresh perspectives that get you thinking differently (like building Minimum Lovable Products instead of MVPs or rethinking the role of the PM). Now-widespread concepts like Kim Scott’s Radical Candor approach to feedback or Superhuman’s framework for product-market fit got their start on the pages of The Review, while memorable turns-of-phrases have become embedded into startup vernacular, like Molly Graham’s rallying cry to “give away your Legos,” or Dave Girouard’s charge to make speed a habit.

Along the way, we’ve searched far and wide for folks to share their wisdom — not just showcasing those who sit at the tippy-top of the org chart or at the helm of flashy name-brand companies (although there have been plenty of those folks, too).

We’ve shared longer company histories, tracing the origin stories of Looker, Upstart, or in our more recent Paths to Product-Market Fit series, Airtable, Webflow, Retool, and Vanta. But we’ve also dug deep into the tactics and the habits of leaders who powered the rise of breakout companies, from Facebook and Instagram, to Dropbox and Stripe, to Airbnb and Amazon, to Figma and Notion — while also drawing inspiration from unexpected corners, like Backcountry’s approach customer service, how Sweetgreen scales intimacy or what software developers can learn from Pixar.

And with a few exceptions here and there (remember when holacracy was all the rage?) the advice we’ve collected here still endures. First Round partner Chris Fralic’s networking advice or Looker founder Lloyd Tabb calling out vanity metrics may be many years old now, but they remain timeless.

Perhaps what The Review is known for best is our longform approach — these aren’t the type of features you can quickly scan in between meetings. But to celebrate 10 years of publishing, we thought we’d try something different. So we pulled together 100 snappy snippets of some of the very best advice we’ve shared on our digital pages over the last decade.

One quick caveat — even these 100 bite-sized bits of advice barely scratch the surface of our massive archive. We’re forever grateful to the hundreds of startup folks who trusted us to share their hard-won wisdom. We started this outlet because we were strong believers that the folks in the trenches building were eager to impart their lessons, not hoard them. All of you have proven, with each and every article we publish, that this community of builders is a generous bunch.

So cheers to the next decade of The Review — and more importantly, to the incredible entrepreneurs who will share their insights and expertise so that the next wave of builders may succeed.

ADVICE FOR GROWING AS A LEADER & BOOSTING YOUR CAREER:

1. If you personally want to grow as fast as your company, you have to give away your job every couple months. Molly Graham on scaling startups.

2. End every meeting or conversation with the feeling and optimism you’d like to have at the start of your next conversation with the person. If you envision running into this person again and how you want that to go, it’ll undoubtedly influence how you navigate a present conversation — usually for the better. Chris Fralic on how to become insanely well-connected.

3. A lot of career advice circles around the idea of “leave when you stop learning.” I think that’s directionally good advice — so long as you have an open mind about what learning looks like. For example, I’ve found that there are periods that may be low-learning on technical topics, but might be high-learning in organizational or team dynamics.” Brie Wolfson on the docs that will boost your impact.

4. Focus on what’s keeping your manager up at night. Often people are so focused on solving their own problems, they don’t think about how their proposed solutions create more problems one level up. Jan Chong on managing up.

What are your boss’s problems and how can you solve them?

5. The quality of your questions determines the quality of the feedback you receive. Instead of asking vague questions like, "Do you have any feedback for me?" or "How can I improve?" ask specific questions to unearth truly constructive feedback. How can this deliverable be 10% better? What would make you “love” this instead of just “like” it? Shivani Berry on becoming a feedback magnet.

6. Founders need to take responsibility for their own burnout and make sure it’s actively managed, like a KPI of the company — and try to do the same for their team. Steve El-Hage on first-time founder lessons.

7. When it comes to emotional health, many people wait until they’re having debilitating anxiety before they start to think seriously about taking action. Think about maintaining emotional fitness less like going to the doctor and more like going to the gym. Just because founders aren’t having daily panic attacks does not mean that they are emotionally fit. Dr. Emily Anhalt on emotional fitness.

8. Pick a company to join by treating the decision like an investor. You are going to be investing your time in this company rather than investing money as a venture capitalist might. Is your next step going to be even more amazing because you spent time here? Elliot Shmukler on his framework for choosing winners.

This is something I’ve picked up from poker: Your probability of winning a hand always depends on having multiple ways to win.

9. The hardest transition as a founder is going from working directly on the product to not. There’s this joy that comes from sitting down to solve a problem and standing up when it’s done and good. Building a company or managing people is never just done. Drew Houston on going from hacker to hypergrowth CEO of Dropbox.

10. I’d rather go down doing it the way that I feel in my heart is the right way to do it. If I got convinced to do it some other person’s way, and it didn't work out, I’d always wonder, ‘What if we’d done it my way? The key is not letting headwinds or tailwinds determine where you sail, but how you sail. To inform how you’ll tack to hit your mark. Wade Foster on Zapier's contrarian fundraising strategies.

11. There’s a happy balance somewhere between being a hermit and a party circuit favorite — and it tilts toward the hermit end of the spectrum. When you’re a founder, every moment you’re not writing code or getting users, you need to be making a conscious choice: Is whatever you’re doing worth your time? Alexis Ohanian on founder do’s and don’ts.

12. When it comes to public speaking, keep polishing your best idea, don’t continue trying to mine for brand-new gems. Think of your favorite song. Do you ever get tired of hearing that song? It’s the same with a strong talk. Anjuan Simmons on building a personal brand.

13. Often, a good impression is a byproduct of deep engagement in a conversation, a desire to learn, or thoughtful work, as opposed to something you aim at directly. Ironically, if you want to make a good impression, focus less on impressing people. Adam Grant on startup lessons from unlikely sources.

14. If I was an Olympic gymnast or an NBA basketball player, all my coach told me was, “You’re doing great!” I’d probably fire them. We want to be world-class Olympic athletes in what we do — and we need brutally honest feedback to get there. Amber Feng on navigating an engineering career path.

15. Separate what you can control from what you can’t. It’s a small way to lift some weight off your shoulders. Take 15 minutes to create a list of everything that you’re worried about. Then label each one as a ‘within’ or a ‘beyond’ to see your sources of stress and anxiety laid bare. Liz Fosslien on weathering startup storms.

16. If you treat your connections as a kind of personal ATM you use for frequent withdrawals, you’ll quickly be disappointed (and overdrawn). Karen Wickre on making connections that count.

The key to networking is to practice a little bit every day — and do it when you don’t need specific help.

17. Goals are great — as long as you have thought in advance about what would make it so that you wouldn’t pursue that goal anymore. Once we set that finish line, we grade it pass-fail. If you quit after mile 20, you failed. If you run 26.2 miles, you passed. Even though running 20 miles is better than not having tried at all. Annie Duke on whether to grit or quit.

18. Before taking your seat across from the hiring manager, prioritize around what’s most important in your new job. Every single question you ask should clearly map back to those priorities — and pack a punch. When jotting down the questions for your interview panel, focus on your deal breakers: What would make you walk away? Anna Binder on questions for candidates to ask in an interview.

19. There’s this pervasive feeling people have that says, “Once I get that funding, it will be okay.” Or “Once we hire that person, it will be okay.” But that’s just living in scarcity and nothing will ever be enough. Katia Verresen on abundant thinking.

When you take time to be grateful for what you do have going for you, you’re training your brain to shift away from stress, to not overreact, and to be open to alternative routes forward. Gratitude is the muscle that makes miracles happen.

20. The demands of a startup are dizzying. To anchor yourself, you must schedule time to write things down. Stacy La on joining as employee 1-20.

21. Focus is doing things with a clear intention. It doesn’t mean you charge single-minded toward a goal. It means you pay rapt and incremental attention to how you need to turn the rudder on a project. Fidji Simo on finding focus.

22. It’s essential to grow with the company — rather than having the company grow around you. Are you constantly looking around to find new ways that you could help the people around you? Instead of being super frustrated by how busy your manager is these days, is there something you could do to help them get more leverage? Cristina Cordova on scaling lessons from Stripe and Notion.

It’s very easy to fall into a mindset where you’re criticizing what’s not going well — it’s much harder to come up with a proposal for making things better.

23. At a big company you're trying to reduce risk, so you're trained to get it right and get it out. At a startup, you have to be a risk taker. You have to get it out, then get it right. You have to be impatient with shipping, but patient with your career. James Everingham on how to scale yourself down, not up.

24. Being vulnerable is one of the most powerful things you can do as a leader because it shows you’re genuine. Being genuine builds trust. Trust is the key to getting anything done. Don Faul on pivotal stories for startup leaders.

ADVICE FOR GROWING & MANAGING YOUR TEAM

25. It sounds so simple to say that bosses need to tell employees when they're screwing up. But it very rarely happens. Picture a basic graph divided into four quadrants. If the vertical axis is caring personally and the horizontal axis is challenging directly, you want your feedback to fall in the upper right-hand quadrant. That’s where radical candor lies. Kim Scott on delivering radically candid feedback.

26. I trust you, make the call” might be the six most powerful words you can hear from a manager. Sean Twersky on high-impact habits for managers.

27. If you’re a manager looking to deepen the conversations you’re having with your direct report, try asking this one question: “What would you save for the end of our 1:1 today? Let’s start with that.” Ximena Vengoechea on becoming a better listener.

28. Anytime you’re telling someone what to do you’re not actually solving the bug. You’re doing a really bad patch. Sidharth Kakkar on architecting an in-sync startup.

29. If you find yourself constantly interrupted by emergencies, find out why. If you’re regularly putting out fires yourself, you’re doing it wrong. Focus your time on how to enable others on your team to put out fires themselves. Sam Corcos on optimizing your time as CEO.

Your job as a CEO is to build fire departments, not put out fires.

30. People need to feel comfortable disagreeing. That doesn’t mean allowing things to flare and get crazy-tense, but also making sure it’s not super-sanitized and folks feel pressure to be kumbaya all the time. When you see the beginnings of healthy conflict, lean into it. Say, “That’s interesting, this feels productive. Let’s talk about it.” It signals that you’re intentionally fostering different ideas.” Jack Altman on running executive meetings.

31. When managers get ready to give hard feedback, they do a lot of prep work. Maybe they write a script or even go through a practice session with a friend. But think about how little work goes into giving folks praise. Russ Laraway on upping your management game.

32. Can you say with confidence that each report would want to be on your team again? If you aren’t sure that the answer is yes, it’s probably no — much like how if you have to ask, “Am I in love?” you’re probably not. Julie Zhuo on essential career questions.

33. Humans have a recency bias, meaning we tend to overweight recent experiences. In management that means I’m mostly paying attention to whoever I talked to last — as the saying goes, “The squeaky wheel gets the grease.” Not everyone is going to be a squeaky wheel. As a manager, you need to be listening for what you’re not hearing as well. Matt Wallaert on impactful questions for managers to ask themselves.

34. Part of being an adult is being able to hear the truth. And the corollary is that you owe the adults you hire the truth. That is actually what they want most from you. Patty McCord on Netflix’s radically honest culture.

35. It’s tempting to only tap your senior people to interview candidates. Less experienced people get a different signal — namely, if they think they can learn from and be led by a candidate. Marco Rogers on interviewing engineers.

36. Not localizing problem-solving is a secret killer of companies. Claire Hughes Johnson on hitting pause to grow faster.

If you don’t consistently teach more and more people how to make the decisions or find resolutions consistent with your company’s goals, you’re going to stall out.

37. The ability to iterate on something until it works is underrated. I'd much rather hire a PM who’s taken a product from version two to eight at a smaller startup, than someone who’s worked at scale, but only shipped initial versions and then moved on. Nikhyl Singhal on crafting product teams.

38. Leading a company means being a conscious custodian of its values. Full stop. Everyone looks at everything you do. If you aren’t living them, nobody else will. It’s a requirement, not a nice-to-have. Jeff Lawson on crafting Twilio’s values.

39. Managers should always be prepared to give away their people, and when the time comes for a high performer to leave, managers will actually be better off for it. Accept that people are going to leave. Especially if you are a first-time manager, it’s much easier to go into the role accepting that someone is going to leave, rather than blame yourself for when it happens. Clarissa Shen on giving away your people.

40. I’ve seen executives write emails all lowercase, loaded with abbreviations and typos, which gives the impression that the time they saved by writing a low-quality email is more valuable than the time it’s going to take others to decipher it. Not only are people frustrated with the poor readability, but other employees will learn not to take writing seriously either. David Nunez on investing in documentation.

41. A lot of times people will complain about a colleague in very specific ways — they do X, Y, or Z wrong. Or they're awful for these reasons. They don't realize that trust is the bigger issue. If you're able to see how important it is in every interaction, that's a big advantage. Anne Raimondi on repairing trust.

42. I decided early on to focus on my strengths, rather than trying to mitigate my weakness with managing. Don’t force people into management in order to progress at the company, just because conventional wisdom says your value is a function of how many people report to you on the org chart.” Dharmesh Shah on co-founding Hubspot.

43. Think bigger. Whatever the idea is, blow it out of proportion and see where that takes you. Come back to me when you've thought about that times 100. Joe Gebbia on design thinking at Airbnb.

Create an environment where people can see a glimmer of something and basically throw dynamite on it and blow it up to become something bigger than anyone could have ever imagined.

44. I grew up playing competitive soccer. We practiced four or five times a week and had games on the weekend — basically spending 90% of the time practicing and 10% of the time actually having to perform. But when you get into a work environment, that notion of practice gets lost. You need to create room for practice and making mistakes. Kevin Fishner on building company systems.

45. The words you choose in critiques really do matter. Who wants to go back to the drawing board after they've been told their work is terrible? Point out what’s good. If you don’t tell someone what they’ve done well, they might never do it again. Katie Dill on giving criticism the right way.

46. The longer someone works for you, the harder it is to change their behavior. The longer you don't deal with something, the less likely you can fix it. Michael Lopp on tough conversations.

47. When you become a manager, progress and feelings are no longer tightly correlated. As an individual contributor, generally, when you were doing well on a project you were making visible progress. As a manager, you can work hard on something for over a year, only to see no progress in the short term and maybe experience a big payoff in the much longer term. Raylene Yung on career advice for engineers.

48. It’s the job of the leader to say, “We're going to climb Everest.” It's the job of the team to figure out the best path up Everest and the requirements for each team member. Amanda Richardson on cringe-worthy data mistakes.

49. You want the leaf nodes across various functions to figure out 90% of the more difficult things on their own. I write multiple emails a day that basically say, "Thanks for telling me, I appreciate this as an FYI, but I don’t understand why you and this other person can’t solve this on your own.” Jean-Denis Grèze on building a culture of ownership.

50. If managers cannot tell you in an instant where they stand on a goal, it’s best to re-visit and retrofit your team’s objectives. Perhaps they’ve outpaced them or haven’t set them in the first place. Regardless of the reason, if it takes them a week to get back to you on a goal, then they probably aren’t monitoring what that goal is. That’s the time to step in. Christa Quarles on scaling advice for CEOs.

51. People can get addicted to yak shaving. An effective engineering generalist knows when to move on. Pay attention to whether they used their time wisely, not just the results. Mike Krieger on co-founding Instagram and building the eng org.

52. Too often we think of DEI and say, “Who are the underrepresented folks in the organization? Here, you all solve this.” And that’s as silly as me saying “I have teeth, I don’t need a dentist.” Founders need to acknowledge and respect DEI the same way you do all your other disciplines. Trier Bryant on putting DEI into practice.

53. If a startup’s first goal is survival, that means evolution. Too much uniformity can halt progress. bethanye McKinney Blount on troubleshooting troublemakers.

Have some tolerance for troublemaking. Otherwise, you might end up with a homogenous organization that a single virus could knock out.

54. Many companies think of engineers in a way that’s like, “Lock them in the basement, throw a pizza down there every once in a while, and hope that code comes out.” But every minute you spend explaining the “why” to an engineer is a minute well-spent. Nick Caldwell on engineering leadership lessons.

55. As a founder, being gregarious, empathetic and thoughtful will get you far with exciting your dream candidate, but nothing will get you farther than an actual demo. Show me the product — I want to see how it really works. Maya Spivak on hiring the right marketer.

56. As CEO, I think of my job as an editor — noticing something, surfacing it and pushing people, trying to hold the team to a higher standard. It's obvious everyone should do that, but no one does it. And that's the point of playing the role of editor and setting standards of excellence. David Cancel on the importance of storytelling.

ADVICE FOR STARTING UP

57. If I had to constrain one, I would rather pick the team and then tackle the idea. People think that a startup is only about the idea. But in some ways, the idea is the most disposable or flexible part of the company. Waseem Daher on the startup happiness formula.

58. You’ll know you understand the customer problem enough when you can predict 75% of what a customer tells you. Keep having these conversations until three-quarters of it is stuff you already know. Christina Cacioppo on Vanta’s path to product-market fit.

59. Building is secondary to delivering value. It is amazing to me how many people come up with a name, hire a team, raise capital or design a logo before they know how they are going to deliver value and to whom. Gagan Biyani on minimum viable testing for startup ideas.

I have a rule: no company swag until the business has at least $250K of revenue or 250k users. Until then, you don’t get to “feel” the benefits of having started a company.

60. If you cannot even describe what your customers are trying to do in simple language, how long will it take you to invent a product they will love? When you can understand and articulate your customers' goals and struggles and anxieties in simple, precise language, your developers and product teams will not have to guess at what to build. Matt Lerner on finding language-market fit.

61. The business model ends up becoming the business. It’s equally important as the market you’re going after and the product that you build. Jay Simons on Atlassian’s unconventional moves.

62. Line up 30 meetings with potential customers before you write a single line of code. You get much better at your pitch after the first five meetings. After the first 10, you start to see patterns. After 20, you really understand segmentation of the market. After 30, you have a really good understanding of what it is that you actually need to go build. Michael Sippey on getting in the van.

63. You must create hilariously aggressive deadlines for yourself, otherwise, you’ll get swept away in unnecessary details that aren’t actually mission-critical. If you’re thinking about color schemes and button widths, your timeline is too long. Tara Viswanathan on pivoting with purpose.

64. Remember that anytime you're trying to get people to buy a new product, use a new service, or adopt an idea internally within an organization, you're asking them to make a choice between something they’ve done before and something new. It’s not about whether or not it's better. It’s about if it is worth making a change? Jonah Berger on catalyzing product adoption.

A startup’s biggest competition isn’t an established player, it’s inertia.

65. Pay attention to what’s working in your co-founder relationship. Start keeping a daily list of all the positive things your co-founder does. What do they do for the company that you appreciate? What can you be thankful for? What would you be unable to accomplish without them? Elevate what they’re getting right, instead of focusing on what’s annoying you. Esther Perel on cleaning up your co-founder fights.

66. A fundraising pitch is a live performance. You have to know it so well that it seems spontaneous. Never read your slides. If you find yourself doing that, you've already lost. Oren Jacob on crafting memorable pitches.

67. How do you know when you’re close to product-market fit? If you don't have it, you feel like you’re pushing a boulder uphill and if you do have it, you're chasing the boulder downhill. Felicia Curcuru on Binti’s path to product-market fit.

68. Even if you have a great product, if you don't have an audience, it doesn't matter. A lot of people say they want to found a startup, but they don’t know what they want to do. You absolutely can’t force it. But you can be thoughtful about building a community while you’re waiting for the right idea or the right moment. Start early. If you want people to listen to you eventually, you have to build trust over time. Ryan Hoover on starting Product Hunt.

69. Nailing down your positioning from the beginning makes everything else easier. You can't be everything to everyone, but you can be something great for someone. Arielle Jackson on positioning your startup.

70. To a founder, their company is their baby. No one wants to hear that their baby is ugly. You really have to choose to hear it. You have to very proactively and consciously shift out of this selling mode of absolute certainty that you’ve used in front of investors and recruits. You have to come back to neutral and go into conversations with customers as an objective observer. Cindy Alvarez on user growth hacks.

71. When somebody has an out-of-the-ordinary reaction to something you are doing, either positive or negative, that’s where the juiciest nuggets are. That means you are onto something. Alex Torrey on gut intuition.

72. The co-founder relationship is 100% in control of those people. That failure is the easiest, in theory, to avoid. But it requires the building of trust, which in turn requires vulnerability. Neither are easy and both are overlooked. Jeff Wald on founder vulnerability.

73. If you're going to be successful as an entrepreneur, the biggest thing is being able to take in conflicting feedback from all these people, many of whom are jaded or have bad habits, and some who are spot on. Nat Turner on finding your startup idea.

The hard part isn’t coming up with ideas; it's distilling all the information you have, 90% of which will be crap, and figuring out what is the good 10%.

74. Find your Goldilocks early users. A lot of startups go in with an erroneous belief that the senior most person should be their primary customer — the SVP of Big Deal Company or the VP of No Time for You somewhere else. Change your approach and recruit the people who would be using the product every day at the director or manager or IC level. You'll get better results. Pete Kazanjy on building a customer advisory board.

75. Sharing the good, the bad and the ugly in your company and investor updates provides accountability and is a forcing function. Concentrate on a single metric. If you see numbers that are less than great, you’ll be tempted to make an excuse, point to another bright spot, or hold off on sharing until things improve. Or you might shift gears and work on another project as a distraction. But you can’t afford to do that. Mathilde Collin on founder discipline.

ADVICE FOR GROWING YOUR COMPANY & YOUR PRODUCT

76. If there's one pitfall that companies fall into, it's that they focus on the why for the business instead of the why for the users. Don’t ask: “Wouldn’t it be amazing if this product could help Airbnb compete with luxury hotels?” Instead, ask: “Wouldn’t it be amazing if users had a variety of high-quality options that made their vacation time even more special?” Jiaona Zhang on building minimum lovable (not minimum viable) products.

77. There are decisions that deserve days of debate and analysis, but the vast majority aren’t worth more than 10 minutes. It's important to internalize how irreversible, fatal or non-fatal a decision may be. Very few can't be undone. Dave Girouard on making speed a habit.

78. To get to the root of how to improve the product and expand the depth of its appeal, focus on these key questions: “Why do people love the product? What holds people back from loving the product?” Rahul Vohra on Superhuman’s engine for finding product-market fit.

To increase your product-market fit score, spend half your time doubling down on what users already love and the other half on addressing what’s holding others back.

79. Three elements define a product: the business, the code and the pixels. Give each a voice in all product decisions. Alex Schleifer on defining Airbnb’s product design.

80. Technical debt is not the scarlet letter. It happens to the best of teams. I’d argue it’s actually irresponsible for a startup not to have any technical debt. Kimber Lockhart on conquering tech debt.

81. Hard numbers tell an important story; user stats and sales numbers will always be key metrics. But every day, your users are sharing a huge amount of qualitative data, too — and a lot of companies either don't know how or forget to act on it. Every customer interaction is a marketing opportunity. If you go above and beyond on the customer service side, people are much more likely to recommend you. Stewart Butterfield on growing Slack from 0 to $1B.

82. A common misconception is that speed is associated with sloppiness, lack of thought and low quality. But speed is not the same thing as running around like a chicken with its head cut off. It’s moving as fast as possible towards the most important thing. Jaleh Rezaei on speeding up your marketing org.

If speed is the yin, the yang is prioritization. You can’t be fast if you don’t know what’s important.

83. One of the biggest mistakes startups make is treating launch like the be-all end-all. It’s like if you just launched, dropped the mic, and said peace out, we’re done. You’re not Bono. Don’t do that. Launching is like the opening move in a chess game. It doesn't mean that much. Caryn Marooney on the best PR advice you’ve never heard.

84. Your customers or patrons make sweeping judgments in their first experience interacting with your creation – especially in the first thirty seconds. The first mile of your customer’s experience using your product cannot be the last mile of your experience building the product. Scott Belsky on shaping remarkable products in the messy middle phase.

85. Delighting the customer always yields better returns than countering or copying a competitor. It’s just a lot harder to do. Andy Rachleff on market leadership.

86. I always tell my clients that there is a kindle strategy and a fire strategy. The kindle is whatever helps you grab those first groups of users so you can validate product-market fit. But then the fire is how you actually scale. Too often people confuse the two. Casey Winters on growth tips from Pinterest and Grubhub.

87. You don't need a big group to start a community, and you don't need to have a fully fleshed-out community engagement plan to start hosting events. Just start gathering, learning and iterating and over time your community will organically find its form. David Spinks on virtual events done right.

Growing a community is more like growing a tree than building a house. You don’t need to have blueprints for what it will all look like from day one.

88. Ignore outward measures of success — capital raised, press, social media followers — in favor of a more meaningful signal: customer behavior. If you focus on all those other things, you’re not fueling your company. You’re just gliding on tailwinds supplied by other sources. You’re reliant on energy that you’re not creating. Payal Kadakia Pujji on finding product-market fit for ClassPass.

89. Without a solid product strategy you end up with products that have a Vegas effect — there are so many flashing lights vying for the user’s attention because each team has its own isolated goals. Ravi Mehta on building a product strategy stack.

90. When testing your message or story, make sure it resonates on the inside first. Your employees are often your toughest critics. They will call bullshit on you faster than anyone else. So if your story is not resonating with them, it's probably not going to resonate on the outside. Terra Carmichael on the top startup comms mistakes.

91. Choose the product must-haves first. Start out with: “The product has to do these three things. Nice to have are these next two things. A bonus are these other things.” Otherwise, if you do get backed into a corner and you haven't quite met the must-haves, it can be really tempting to ship anyway. Caitlin Kalinowski on prototyping lessons from Apple and Oculus.

92. “Why would a customer not want this?” is often a far more interesting question than why they would. Rick Song on asking why it won’t work.

Oftentimes the question of why something won’t work uncovers the element that actually does make it work.

93. Your annual plan needs focus — likely more focus than you might feel comfortable with. When you leave the planning process wondering if you put too many resources behind a single bet, that’s the bet that ends up succeeding. Bold ideas need bold resourcing. Lenny Rachitsky and Nels Gilbreth on annual planning advice.

94. Even if you have billions of users, you won’t find any texture in your data if it’s siloed. Call individual people. Start now. Do it often. Software is getting people to think and behave in new ways. A/B testing is monitoring without interacting. Put down the binoculars. Pick up the phone and have a real conversation. Lloyd Tabb on ditching vanity metrics.

95. Staying savvy on good products and trends in the broader ecosystem is super important. But that’s different than focusing on your direct competitors and getting into a myopic state of, “Oh, we’ve gotta build this because they did.” That's counterproductive. Andrew Ofstad on Airtable’s path to product-market fit.

96. You can’t close large deals, tell your brand’s story or improve the product without the voice of the customer. If you don’t have at least a few customers who are willing to go to bat for your product, what programs can you build to start creating those champions? Kalina Bryant on customer advocacy.

97. Feature commits for customers are tech debt for product teams. You limit your flexibility — and what’s more valuable to a startup than the ability to change course quickly? Nate Stewart on how product strategy fails in the real world.

98. Resilient founders don’t ask “Which competitor are we scared of?” Instead, it's “What's the new product that would terrify us the most if it were launched tomorrow? What fully-formed company would be an existential threat to us, whether it exists or not? And if it doesn’t exist, why aren’t we building it?” Bob Moore on founder resilience.

99. It sounds abundantly obvious, but when you’re a designer you’re often knee-deep in a set of features rather than zooming out to why it was purchased to begin with. Too often designers focus on talking to customers that already exist, not prospects or customers that could exist. Hareem Mannan on managing a high-impact design org.

100. Treat customer development as a one-on-one with a direct report — you just want to ask the hard questions. Ryan Glasgow on clearing product hurdles.

As a startup founder, you're constantly telling stories. You tell the story of your company's origins when you pitch to investors. You craft narratives about your product when marketing to customers. And you shape an inspiring vision to rally your team. Storytelling is woven into every aspect of building a startup.

But in the midst of building the product and all of the other things on a startup founder's plate, it's easy to lose sight of the impact your stories have on your business — how you narrate your startup's journey influences everything from funding and sales to morale and team cohesion.

It’s why every startup leader should practice flexing their storytelling muscles and carefully hone this skillset. To help warm these muscles up, we’ve rounded up some of the best advice about storytelling in business that’s been featured in archives of the Review.

Learn from folks like Oren Jacob, the man behind the storyboarding process at Pixar, to First Round’s own Marketing Expert in Residence Arielle Jackson on how to position and present a successful startup story. We’ll feature tested frameworks for leveling up your business storytelling skills for all sorts of different audiences.

WHY STORYTELLING IS SO IMPORTANT IN BUSINESS

Storytelling isn’t just the domain of content creators, marketers or PR pros. The ability to tell stories that inform, persuade or inspire supercharges every part of company building.

“When we look at what visionaries really succeed at, they give us a confident, consistent and coherent plan that makes us feel safe,” says longtime Google product leader Tyler Odean. “We trust them not because their vision is perfect, but because they have it under control. They communicate clearly without giving us all the answers. What most people think of as vision is actually persuasion.”

And when it comes to persuasion, companies typically appeal to the left side of the brain, like logic, pricing and specs, says Andy Smith (a startup marketer, advisor, and expert storyteller). Emotion, however, has proven to be the better marketing tool. Simply put, well-told stories earn attention. Storytelling in business can be a powerful tool to help you connect with people emotionally, simplify complex ideas, humanize your brand, inspire action and spark creativity.

FOUR WAYS TO LEVEL UP YOUR STORYTELLING

But the way you architect and tell a company’s story is (and should be) quite different from the way you’d tell a story at a party. Here is the four-step checklist for crafting a compelling business narrative.

1. Identify The Purpose

Are you trying to persuade investors to take a chance on your startup or convince top talent to leave a BigCo job to take a chance on your startup? Start by narrowing down the purpose of your story — think of this as sketching out the story structure.

For advice, we turn to Arielle Jackson, our Marketing Expert in Residence at First Round and a former marketing leader at Google and Square. Jackson has advised hundreds of startups over the years to communicate the exact story they want to tell, and she asserts that the bulk of this comes down to proper positioning.

“Aligning teams, hiring the right people, developing the best product, communicating the value of your work — the list goes on. It all starts with positioning,” she says. “You need to position yourself in the mind of your user. That requires taking your potential audience into account, assessing your strengths and weaknesses, and considering your competition. People are busy. You have to know who you are.”

2. Pinpoint The Audience

Once you have the purpose of your narrative nailed down, the next piece of the storytelling puzzle is to fine-tune the details so it resonates with the right audience. Just as a product manager zeroes in on a customer persona, expert storytellers do the same with narrowing down an audience persona.

But for the times that it’s not so obvious who the target audience of your story is, this may take a bit of pre-work. Jackson offers some helpful questions to ask yourself before formulating your next business story:

• What’s different about the way your product/service works?
• Why do you do what you do?
• What is your broadest circle of prospective customers? Start with something like “Android users” or “people without cars,” and then try to get more specific, ending up with a profile of an individual model user.
• What pain points are these customers experiencing? Be as clear and specific as possible. What emotions do customers associate with these pain points?
• What other companies solve similar problems? Don’t just list your competitors but also their strengths and weaknesses compared to what you’re doing.

3. Sculpt a Structure

We’ve all been twisted up listening to a rambling story, with no discernible beginning, middle, or end in sight. At the very mildest, it’s a nuisance to the listener. At its worst, a poorly told story can have the exact opposite effect on your audience; it can persuade folks why they shouldn’t listen to you.

It’s critical to follow some sort of structure to anchor whatever narrative you’re telling. “You need to take the whole room on a journey together,” says Oren Jacob, the founder and CEO of the entertainment company PullString and former CTO at Pixar. “This means there has to be a narrative arc with a beginning, middle and end. When you’re in command of your material, creating this structure is in your control.”

One tactical way to make sure you are landing on a structure that weaves in all the points you want to hit home is to ditch chronology altogether. “Chronology matters much less than having your story follow an interesting arc,” says Smith. "And as luck would have it, the stuff you need to hook people doesn't tend to happen early on.”

Unless you’re telling the story of how to land a plane safely or the proper assembly of an IKEA bookshelf, resist the urge to begin at the beginning.

Smith argues that events need to build, one after the other, emotionally rather than sequentially.

4. Weave the Storytelling Elements Together

So you called a cab, but no one’s showing. The only thing the cranky dispatcher will say is “He’ll be there in 15.” You call back in 15, and he now says, “Driver’s on the way. Any minute now.” Click. It’s cold, it's getting dark, and you’re already late. Wouldn’t it be great if there was an app that let you tap into an unused supply of empty cabs and cars to get you where you want to go, perhaps with a little style?

So goes the legendary inspiration behind Uber, a story now encapsulated in a single tagline: “Everyone’s private driver.”

It’s also a near-perfect example that combines steps 1-3 seamlessly. Andy Smith argues this anecdote followed the proper business storytelling formula.

Uber took into account its purpose (a private taxi competitor and startup) sprinkled in messaging for a hand-picked audience (potential customers who had felt the pinpoint that Uber was solving) and used a clear beginning, middle, and end structure to tie it all together. The result painted a compelling picture that a real problem in this area existed while also offering itself as a solution. Blending in elements like conflict, a main character and relatability made this an even stronger pitch.

HEAR FROM THE EXPERTS: HOW TO ACHIEVE STORYTELLING SUCCESS

Like the Uber example above, sometimes, the best way to get a grasp on storytelling skills is to listen to a terrific one. So we’ve rounded up four storytelling experts who have shared their hard-won wisdom with us on the Review over the years for additional tips to help boost your storytelling abilities.

Practice how your story will land by running the Bar Test

Nicole Kahn knows a thing or two about delivering a compelling presentation. Now the VP of Design at Carta, Kahn has spent her entire career carefully crafting thoughtful designs and projects for innovative workplaces like IDEO and WeWork.

One of her favorite tips to lean on when starting from scratch on a new presentation is to run the Bar Test. “Something really important happens when you’re at a bar,” says Kahn. “You use direct language. You make sure that what you’re saying is entertaining and engaging. You don’t quote tons of data. You don’t use overly corporate language — except maybe in air quotes.”

Kahn argues that this proves that we all have an innate sense of what makes a good story, but we tend to forget it once we walk into the office or join a Zoom room. She challenges anyone taking on business storytelling to think: how would I give my presentation at a bar?

By bringing the Bar Test into the work environment, we answer this question: What’s the point?

To run the Bar Test, Kahn has her team talk to other people — often strangers — before they start putting presentations together. “We tell them our story. We verbalize it. We grab a colleague who’s completely unfamiliar with what we’re doing and buy them a beer or a coffee and spend 15 minutes to see if they understand the point of the presentation,” she says.

Lean into your authenticity to boost your credibility

Storytelling in business isn’t just about being able to tell tales of success, but it’s also about knowing the power of telling stories of failure or doubt.

Don Faul, CEO of Crossfit and former Head of Operations at Pinterest has spent the better part of his career leaning on authentic storytelling as a way to establish trust as a leader. He learned from his early career at the U.S. Naval Academy that all good leaders need to be able to tell what he calls the “failure story” to be credible.

“If you’re willing to tell everyone on your team about your mistakes, your shortcomings, what you’re currently working on to get better, you seem more human. It’s easier for people to connect with you. They have an easier time believing what you say, and that you’re taking their wellbeing into account,” Faul says.

Being vulnerable is one of the most powerful things you can do as a leader because it shows you’re genuine. Being genuine builds trust. Trust is the key to getting anything done.

Commit it to memory

Sketching out the beats of a story is just one part of telling a compelling narrative. But if your delivery is stilted or you’re just reading off your notes, even the most well-designed stories can fall flat. As Oren Jacob puts it “A pitch is a live performance. You have to know it so well that it seems spontaneous.”

This spontaneity is key to helping your audience pay attention, remember the information, and be persuaded to take action. Committing your story to memory, in whatever form that takes, will help inject the necessary emotion and authenticity to persuade your audience. If that means practicing your pitch, presentation, or speech in the mirror at home for a few hours each night, do it, says Jacob.

Never read your slides. If you find yourself doing that, you've already lost.

Finally, remember that great stories are inspiring.

“You have to make investors believe how much you believe in it, and how much you want to go on that journey with them — even if neither of you knows how big it can get," Jacob says.

Image credit: Constantine Johnny for Getty Images