, a new company in the data analytics space. While their prospects seemed bright, their timing could have been better — three days later, Lehman Brothers collapsed.

Their startup set out on a journey with just about everything working against it: inexperienced first-time founders, a crushing economic environment and a big bet on where the industry was heading. The path was twisty and full of challenges, but by 2016 the duo had amassed hundreds of customers and RJMetrics was scooped up by 

“But as exits go, it was more of a base hit than a home run,” says Moore. “The most valuable thing we took away from RJMetrics was the muscle of how to fight hard and the painful lessons that came from surviving a turbulent environment — only to later lose the long game. Take our old competitor 

 last summer for $2.6 billion. They ate our lunch, even though we had a four-year head start.” (For more of the nitty-gritty details on where things went south in their battle against Looker, check out Moore’s 

That’s a mistake Moore vowed not to make again. Equipped with a sharper vision and nearly a decade of experience, he and Stein spun off their second company, 

, using technology they retained in the RJMetrics acquisition. In just two years, they netted a far better outcome when they sold to Talend in 2018 (with only 30 employees and no outside funding). Now, Moore’s on his third venture — and he’s swinging for the fences. His current startup, 

, is a platform that aims to help companies build more valuable partnerships through data-driven collaboration. Buoyed by industry tailwinds and 

, he and his team seem to have plenty of runway ahead.

While First Round invested back in Crossbeam’s early days (and coincidentally, Looker’s as well), that’s not the reason why we were eager to talk to Moore here on the Review. With multiple startups under his belt, he’s a seasoned company builder — one who has cut his teeth as a first-time founder during some tumultuous times.

“With my first startup, we survived the 2008 downturn and got to an exit, which is more than many startups of that vintage can say. But I was so heads down focused on that ‘grinding it out’ mentality that I over-indexed on it when the time came time to push for growth — and we got lapped by the competition. 

There's a difference between building a company that survives and one that thrives, and it took me too long to adjust when it was time to switch gears

,” says Moore. “Now it seems like the pendulum is swinging back around again to a 

 mentality. Building a resilient company might be coming back in style, but this time I’m not taking my eye off of the upside that comes after.”

In this exclusive interview, Moore opens up about what he’s learned after more than 12 years in the founding trenches, from building in bear and bull markets to avoiding “meh” exits and tackling the fickle nature of product/market fit. Moore compares his experiences across multiple startups to cull together a collection of seven lessons — the ones he wishes someone had shared with him back when he was treading choppy waters as a first-time founder.

1. A strong long-term vision will help you weather intermittent storms.

To start, Moore stresses that no amount of agility can replace a strong company vision. “A good vision means you have strong first principles. The products can evolve. The team can change. The market could hit a downtown. But if you are relentless and consistent in your pursuit of a well-formed vision, you'll be able to weather most storms," he says. "The difference between having a crisp vision and muddling through without one will alter the trajectory of your company — I’ve been on both sides of that coin.”

RJMetrics was an example of the latter. “We could see an area of opportunity when we got started, but we didn’t actually have a clear vision for what we were trying to build and why it would succeed. We had one word — data — and the rest of our ‘vision’ could twist and turn based on the most recent thing we heard from a lead or customer. A strong vision could have been our backbone, but we just didn’t have it. That was no way to build a category-defining company,’” he says. “Because we weren’t steering with a solid strategy, we pursued all these product micro-optimizations and landed ourselves in a place where we created a company that creates 

Stitch was a different story. At his and Stein’s second company (the one that bagged a better exit), Moore says they had a vision from day one. “Our vision was fully baked when we stepped up to the plate. We said, yes, there's a problem space, but more than that, we have a very specific point of view on how the problem should be solved. It wasn’t just that people were feeling the pain of scattered data, but that we actually had a vision around a solution that would also fit into the market dynamics at the time, specifically how massively scalable data warehouses like Amazon Redshift, Google BigQuery, and Snowflake were coming onto the scene,” he says.

“Plain and simple, here’s the formula you need to nail down: 

Here's what we’re here to do, here’s why we'll be the best at doing this very specific thing, and here are the tailwinds that make now the right time to do it

. We’re seeing this now at my current startup, Crossbeam, too. We started this company with an extremely specific vision for what the world should look like when this data collaboration problem is solved in the best possible way, not with something generic like ‘Partnerships are a pain, let’s go figure that out.’”

What are we going to do? What is our unique vision behind it? That’s an existential, table-stakes prerequisite to building a resilient venture-scale company. Even with the best team in the best market, you’ll hit a ceiling without these ingredients.

2. Product/market fit doesn’t mean you’re in the clear.

Getting to product/market fit quickly is often seen as a panacea for startups, but Moore has learned it's not enough to simply find it — you have to keep it too. “

You can’t survive a downturn by shutting your eyes and grasping onto your product/market fit for dear life. Shifts in the market make it even more important to be at the wheel and keep your eyes on the road

This was the trap Moore encountered at RJMetrics. “

Often people talk about product/market fit as if it’s a video game level you unlock and then it’s smooth sailing from there

. That’s a mistake too many founders — myself included — have made. When we started RJMetrics in 2008, I’d say we were ahead of the market. SaaS was still barely a thing, and no one was doing what we were doing. We iterated for four years, onboarding early adopters and building a nice little bootstrapped business,” says Moore. 

“And then all of a sudden, the market caught up to where our product was. And that's when we had a crazy product/market fit period. From 2011 to 2013, we couldn’t keep up. The leads were falling off the desk. We couldn’t hire reps fast enough. It was almost unexplainable. We exploded in growth and size, so it seemed like everything was on track. But during that period, we barely changed the product. We became inflexible. The market was moving, but our product wasn’t. So by 2015 or 2016, the market had moved out ahead of us, except we didn’t see it. We kept executing — and got left behind.”

Product/market fit isn’t a diploma you hang on your company’s wall. It’s a moving target that you constantly have to monitor. Take it from me — you can find it, only to watch it slip through your fingers.

Product/market fit is the gap between the product that you built and where the market is at any given time.

 Picture a chart with time on the X-axis and progress on the Y-axis. Your product and the market are two separate lines with different slopes that move over time. At RJMetrics, they intersected at this beautiful moment, which enabled us to build a lot of value. But then we lost it. If you go long enough without changing the slope of your product to keep up with the market, they will just drift further and further away.”

3. Looking for your biggest competitive threats? Follow signals, not noise.

While understanding your competitive landscape is important, Moore’s come to learn it’s not nearly as crucial as double-checking your company’s path and course-correcting if you fear you’re adrift. 

The best way to build resilience is to stress test your own assumptions constantly

This might be a surprising takeaway — after all, given the history, you could forgive Moore for being extra wary of competitors these days. But in his view, RJMetrics didn’t get lapped by Looker because they weren’t paying enough attention to their competitive landscape — they were paying 

, we didn’t even consider them to be our competition. But fast forward six years, and my co-founder and I are scratching our heads about 

“We spent so much time spinning our wheels looking at noisy CEOs and big incumbents. We always had our eyes peeled for that next Y Combinator upstart that would come along and threaten our market position. But in the end our biggest competition came from a group of modest, hard-working operators whose experience gave them a sharper vision,” he says. “For all the young iconoclasts on Twitter, there is an equal number of quiet experts who pose more credible threats. Those were the founders who ended up taking home the gold medals in our industry while we settled for bronze,” says Moore.

The reason they ended up on that lower podium? “We got so heads down in executing on what we thought was a good idea in 2008 that in the course of those next eight years, the ground shifted underneath our feet. This entirely new way to approach the problem came forward,” he says. “I was worried about companies like GoodData and Domo, the ones who were basically doing the same thing we were. What we failed to realize is that Looker was serving the same audience on the same value proposition, with a more appealing product approach. 

We built the proverbial ‘faster horse’ while they were busy inventing the automobile

I don't worry about competition, I worry about my own vision being wrong, which creates an opportunity for competition to succeed. If anything, I think we spent too much energy thinking about the noise everyone else was making and not enough thinking about our own place in the real market.

“To get more tactical, I found it’s helpful to harness that nervous energy and channel it toward something more productive,” he says. “For example, later on in RJMetrics’ timeline, we started asking ourselves a simple question: 

What's the new product that would terrify the most us if it were launched tomorrow?

 Our answer was something that could connect the dots between all these new cloud data warehouses that were taking over the market and the emerging tools like Looker that provided a better user experience for analytics. That product would be the missing link in a value chain that would completely disintermediate RJMetrics. Rather than wait for it to show up and finish the job that Looker had started, a small team at RJMetrics built it as a hackathon project. That product ultimately became Stitch, which we successfully spun out and built into a substantial standalone company after RJMetrics was acquired.”

Resilient founders don’t ask “Which competitor are we scared of?” Instead, it's “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?”

4. Resiliency starts at the top — and it's not something founders can outsource.

While navigating the rough waters of finding a vision, external conditions and product/market fit at RJMetrics, Moore leaned on what he thought was sage startup wisdom: Don’t go it alone. He turned his attention to hiring executives to help round out the leadership team.

“We burned through two VPs of Sales before we figured out that it was product issues — not sales fortitude or go-to-market execution — that was holding us back. So we set our sights on finding the perfect VP of Product to solve our product woes. After months and months of recruiting, onboarding, and testing, it turned out the problems with the product were rooted in the vision of the company,” he says. “We were right back at square one. I wish we’d spent all that lost recruiting energy working on the fundamentals of our vision so those awesome people could have had a better product to build and sell.”

There's a difference between delegating and absolving yourself of responsibility. Don’t let that new, fresh-faced exec be a crutch that causes you to ignore your responsibilities as a founder and CEO.

“As the founder or CEO, you can’t slap on blinders for key aspects of the business. 

You’re in really, really dangerous territory if you assume that anyone is going to show up and magically fix your functional problems

. When you pin your hopes on someone coming in to fix it, what you’re doing is absolving your responsibility to help crack that problem and removing all your institutional knowledge as a CEO. That’s a huge mistake.”

For example, if you’re a technical founder 

, don’t just wash your hands of this function because you hired someone with experience. “Even if you have no clue how to execute a marketing campaign, you don't know all the acronyms of online ad buying, and you don't know what looks good, you’re not off the hook. You still need to build expectations around what they will deliver, a culture that inspires them and the credibility to hold them accountable. You can’t do all that from a distance, especially with a small team,” says Moore.

It’s impossible to outsource the hardest parts of being a founder. Investors and senior hires are not a dumping ground for your tough decisions. No one’s coming to save you.

built all of his companies outside of Silicon Valley

, you might expect him to be firmly in the remote work camp. But that hasn’t always been the case. “My first job was in finance where facetime is everything. That was ingrained in my work habits, so I spent the early part of my career as a founder demanding everyone be in the office,” says Moore. “

But I’ve also had the experience of taking out a multi-year lease on an office space that outlasted our company

 So over time, my mentality changed drastically.”

Moore notes that the cloud-based tools of 2020 are light years ahead of where they were when he started his first company. “The conventional wisdom as recently as five years ago was that you’re either all-remote, all-office, or you’re doomed. That’s changing along with a new generation of collaboration tools and mentality shift among modern workers. Crossbeam is a ‘remote-friendly’ hybrid that keeps office space available for local employees but also has a large remote workforce,” he says.

With unpredictable global events like the outbreak of COVID-19, the trend toward remote-friendly and remote-first workplaces will only continue, Moore says. “It adds to your company’s resilience — whether that’s an economic downtown, office space troubles or an intense travel schedule. When we switched offices early in our journey at Crossbeam, we asked everyone to work from home for a week and faced minimal disruption. Or when we we sent our team to conferences all over the world, we knew the work will still get done because they had that remote-friendly working habits already. Physical location doesn’t cause a gap in efficiency for anyone, and that’s by design.”

The key to making this work all year round is to go all-in, even if some of your team members return to showing up to an office. Here’s a peek at Moore’s remote-friendly playbook, designed to scale, but applicable for teams as small as two:

• Zoom links are required for every meeting by default, and there can be no assumption that your attendees will be there in person, even if they are regularly in the same office as you. Showing up virtually does not require an apology or explanation.

• Make your remote team members first-class citizens. If a benefit, perk or experience is created for your in-office team members, find a way to create parity for those who aren’t in person. That means mailing items given to your in-office team to remote workers — or if you cover lunch for your in-office team, send your remote team a gift card or stipend for food delivery.

• If your leadership team has a tendency to work in company offices, make it a point to have them attend some meetings virtually anyway, especially for big company events like All Hands meetings. "We’ve taken meetings in different conference rooms or worked from home for part of the day to make this happen," says Moore. "This helps them build empathy for the remote experience and develop the sense of inclusion for remote team members."

• Find the places where shoulder taps and overheard conversations are a convenient crutch, and make them obsolete. “This means you need clearly-measured and communicated goals (we use OKRs), repositories for company history and curiosities (we use a #founder-ama channel in Slack), and 'where you need it, when you need it' repositories for key shared knowledge (we love fellow Philly company 

6. Assemble your wishlist of would-be acquirers — and start building authentic relationships ASAP.

“It’s a founder trope to say ‘we didn’t start this company just to sell it’ — and we used to say that a lot,” says Moore. “But we drank so much of that Kool-Aid that we found ourselves scrambling when selling became our best option. 

We failed to cultivate relationships with potential buyers from day one,

 so when a high-pressure offer came in, we didn’t have the time or the network to spin up a competitive process fast enough. We may have left some serious value on the table as a result,” he says.

“My co-founder Jake Stein nailed this at our next company, Stitch. He cultivated relationships with the CEOs and heads of corp dev at all of our target acquirers from day one. When we found ourselves in a similar situation with that business, he spun up a fast and efficient process that gave us conviction that we were choosing the right deal for our company and our team,” says Moore. “Now, I’m using Jake’s playbook again at Crossbeam.”

“You don’t kick things off by saying, ‘Hey, you might buy me one day.’ You cultivate them by genuinely looking for synergies between what you're doing and what these other companies are doing. That might be a product integration, it might be go-to-market partnerships. It might just be information sharing. But those relationships require a genuine — not manufactured — motive to take hold. They don’t come together overnight.”

7. Turn self-care into a strength to bounce back from failure.

A disappointing exit or a series of tough scrapes can cast a long shadow on your next play. “When you get beat, when your strategies aren’t working, when you have to do layoffs, when you announce a modest acquisition — it’s easy to hang your head,” says Moore. “It’s not exactly confidence-inspiring to see your first venture go somewhat quietly into the night. After the modest RJMetrics outcome, I was questioning whether I could ever raise money again. What was I going to say? ‘Hey, I’m the guy who pounded his chest before, trust me this time?’ It also gets personal, fast. You think, ‘Have I wasted these years of my life?’ or ‘Is my career as an entrepreneur over?’”

As a first-time founder, it’s easy to believe that the only return on investment you get from your startup is the proceeds from your exit. “Turns out the experience was the real payoff,” says Moore. “It wasn’t until I was building my second company that I realized the upside of falling on my face so many times at the first one.”

. (He’s personally come to rely on exercise and 

.) “Don’t underplay that aspect, it’s truly a big deal,” he says. “

Sometimes the company's operational failures are actually outputs of the founder succumbing to decision fatigue. Or becoming overly paranoid or personally stressed. Or not having the energy to build the support system that they need to succeed

When it comes to bouncing back from failure, there are many factors outside of your control. But all founders are in control of being honest with themselves about what they need to operate at their fullest capacity — and that includes when (and how) to recharge.

Personal maintenance is the safety net that catches you as you’re weathering failure. It’s not just how you protect yourself when things go poorly, it’s how you focus your superpowers when things are going right.

TYING IT ALL TOGETHER: THE FOUNDER’S CHECKLIST

This last lesson is particularly top of mind for Moore these days. “I’m trying to stay conscious of how I’m susceptible to these same forces in a different way now. I’m pedal-to-the-floor with Crossbeam, but I don’t have blinders on about what it means to be building a company in the turbulence of 2020. Business fundamentals are as important as ever, and legitimate product/market fit is still the most important input to making those fundamentals scale,” he says. “That long shadow of my previous experience is still there. I'm also a little older now. I have more gray hair and I've got a beautiful daughter at home who deserves a dad who is present and reliable, so I don’t have time or energy to waste,” he says.

That’s not to say that repeat founders don't make mistakes anymore, it's that you get to make a whole different class of mistakes

 — including the risk of living in the past. If I had to summarize what’s different now with Crossbeam, it’s that I have more confidence in the basics. More than a decade of muscle memory makes a subset of my day-to-day decisions a bit less fatiguing, leaving more mental energy for looking ahead to uncharted territory.”

To distill all of the work it took to get there, here’s a quick checklist of the resilient founder lessons Moore’s picked up over the years:

• Sharpen your specific product vision instead of tackling general problem spaces. Be able to answer these questions: What specific thing is your company here to do? Why will you be the best at it? What tailwinds are at your back?

• Remember that hitting product/market fit doesn’t mean you're golden. Keep careful tabs on the changing slopes of the market and where your product is — or isn’t — meeting it.

• Take note that your biggest competitors can come from surprising sources. Focus on your place in the market to make sure you’re not creating an opportunity for others to succeed — and ask why you’re not building the competitive product that’s keeping you up at night.

• Learn the difference between delegating and absolving as you bring on executive hires. Don’t try to outsource the tough calls and foundational problems to new blood.

• Be cautious when it comes to long leases and try to broaden your thinking on remote work.

• Cultivate genuine relationships with potential buyers on day one to reduce the risk of FOMO when negotiating a sale on a tight timeline.

• Weather the storms of failure with a strong support system and set of self-care strategies. The most important thing is to not go away unless it’s on your own terms.

B.Moore2.jpg

Bob Moore's first brush with life as a founder started in 2008—three days before Lehman Brothers collapsed. Since he cut his teeth as a first-time founder in turbulent times, he's gone on to build two other companies. Here, Moore shares the lessons he's learned along the way, from weathering bear markets and losing out to the competition, to finding (and falling out of) product/market fit.

This Founder Built Startups in 2008, 2016 and 2018. Here’s What He’s Learned About Resiliency

’s Chief Product Officer this past summer, 

 has kept busy. Apart from time spent weighing options for his next adventure (and a much-needed Alaskan cruise vacation with his family), he’s been advising folks at every end of the startup spectrum, from scrappy early-stage founders to heads of product at some of the biggest unicorns.

That’s because, whatever stage your company is in, Singhal makes for a perfect sounding board. He co-founded three startups: one that failed, one that got acquired by IBM, and one that was scooped up by Google in 2011. He then settled in for a stint at the tech giant, launching Hangouts and assembling the product team for Photos before taking up the reins at Credit Karma, where he oversaw the launch of a half-dozen new product lines and grew the product team from 10 to 75 people in four years.

Taking advantage of that expertise, founders and product leaders at companies big and small bring him their toughest questions: When should founders hand over the product controls? What should you look for in a PM? How do you structure the team? How do you balance strategy and innovation with execution and predictability?

Underneath each of these issues are minefields that could trigger any number of missteps. “Founders often fail to take the necessary steps to deliberately scale the product function, and then the wheels start to fall off when hypergrowth hits,” says Singhal. “Other times, they try to hire the product team of the future far too early. Driving roadmaps and getting more strategic are important problems that 

 exist someday, but in the earlier stages it’s more about getting the trains to run on time.”

That’s why Singhal always finds himself dishing out the same piece of advice: 

You need to craft a product team to match the phase of your company

. In other words, from the early struggles of 

, to the “teenage years” of optimizing products 

, to the blistering pace of hypergrowth, every phase of a startup’s life brings a unique set of challenges for the product org.

And the consequences of a mismatch can be far-reaching. Premature product hires can feel crowded out by the founder who’s still 

. Or later-stage execs can find themselves with a product team that’s great at taking the ball and running with it, but struggles to come up with ideas for new product lines on their own.

The ability to right-size your product team for the challenges your company faces is a secret weapon.

To help founders and product leaders get a better sense of those challenges — and the team they’ll need in place to solve them — Singhal shares the phases he believes a product org goes through as a startup matures. (Though they’re distinct from one another, he notes that companies don’t move through them overnight. “They require months or even years or rewiring, with the old adage of ‘What got you here isn’t what gets you there’ serving as your guiding light,” he says.)

 The company’s goal is to experiment as much as possible to find product/market fit. Product is tasked with painting the founder’s vision, and is working as more of a service or project management function.

 It’s time to double down on what’s working. As founders get more busy scaling the company, product’s role is to own collaboration with other teams and drive communication while predictably delivering releases to improve the product.

 This stage is about innovating while scaling the existing product. The product team needs to articulate the strategic roadmap, translating the mission and long-term vision of the company across multiple quarters. This requires a blend of introducing new products and supporting existing successful ones, while starting to add a new layer of team leadership that can make decisions on their own.

 Company becomes market leader (think FAANG). “Inside the building” problems stack up, focus shifts to sustaining growth and the innovator’s dilemma becomes most acute.

In this exclusive interview, Singhal shares how product teams can transition between these stages gracefully. Focusing on the first three phases, he’ll cover how the product team needs to change, what the founder’s role should be, the mistakes that are too easy to make and what to look for when hiring. Whether you’re an early-stage founder bringing on your first PM or a later-stage head of product seeking to build a cadre of leaders and better structure your team, you’ll find tested tactics in his hard-won wisdom.

Common questions founders have at this stage: 

When’s the right time to add the product function to our startup? And what should I expect it to contribute at this stage? 

What should I look for in our first product hire? Do I hire someone who can grow into head or VP of Product? Or a more junior player I’ll later layer above?

 came up with the name for this phase, and I love it,” says Singhal. “It’s about stumbling around, trying to build something people want. 

This stage is the opposite of ‘up and to the right.’ It’s fast failing, unsure of where you’re heading

. It can last years — and 99% of most startups never make it out.”

The role of product vs. the role of the founders:

Singhal has found that many founders tend to feel guilty about “not investing in the product team” in this phase. But in his experience, it’s not worth losing sleep over. “They’re doing the exact right thing,” he says. “Founders should own 

finding product/market fit before the end of the funding runway

, which means coming up with the product vision and determining what to build and in what order. Early engineers help them get there faster.”

So where does the product function fit in? “An early product hire isn’t joining during this phase to help with long-term planning or creating the next big thing,” Singhal says. “Instead, it’s about quickly painting the founder’s vision, ideally accelerating through the ups and downs of finding something that customers want.”

 at this stage. “I’m sure some product folks will bristle at the label,” he says. “But if you aren’t able to ship reliably, you can’t plan ahead. Most PMs begin their careers focused on execution and tactics — and nascent product orgs should start in the same place.”

A startup’s first product hire needs to focus on understanding how to partner with engineers and execute predictably. “That’s building schedules, running standups, publishing product requirements and coordinating releases. Once you understand the details of how it all fits together, then you can prioritize work,” says Singhal. “Goal-setting is a natural outgrowth of that. And once you start talking about goals, you need to zoom out a level higher to say, ‘Well, where do we need to go? What's the strategy? How can we figure out a roadmap to deliver on that?’ Boom, you're doing product management.”

But you can’t expect to get into all of that upstream work in the drunken walk phase. “At the very beginning, you're lucky just to be able to plan a few steps ahead — you don't have the resources or the data to do too much more. You can’t forecast what customers will want or look six months ahead. There's no value in constructing an elaborate roadmap, and, in fact, it works the opposite way. The closer you are to the ground, the better.”

In the “drunken walk” phase, it’s about scrappy experiments and moving quickly. Management, process and structure are ingredients that haven’t been added in yet, and any early product hires are playing supporting — not starring — roles.

For Singhal, the founder’s mistakes in Phase 1 all come down to timing. “Founders either bring on a first product hire too early or too late. I certainly have been guilty of both,” he says. Here, he outlines the risks of each:

: “Finding product/market fit is hard, so after failing for a few quarters it’s tempting to bring in a PM who can come up with winning ideas. I made this mistake in all of my startups,” says Singhal. “Sometimes the PMs would try to project a grandiose vision — but that was often uninformed or unrealistic. Other times, they didn’t feel empowered to suggest a new direction to early employees. If you’re a founder who views product as something that’s inherent to your identity, you need to find your own way. Otherwise you risk sidelining yourself when you still want to be on the field.”

 “Founders often want to hold onto the product reins as long as possible. But eventually, they no longer have the time to do the everyday product work,” says Singhal. Here’s why that’s problematic: “Everyone on the team needs context. Otherwise, engineering will deliver features that miss the mark or take too long to deliver, since the key reasons for the capability are unknown,” he says. “Sharing that context is easy when you can all sit around a table, but especially once you’ve grown to several engineers and added a designer, it can quickly break down. If you talk to the engineers and their feedback is, ‘I'm not sure I understand why we're building what we're building and when,’ that’s a sign that details are already slipping through the cracks. Bring a product person on to help facilitate that context.”

“When I start talking about how product work is more like project management in this phase, some founders immediately jump to ‘Okay, I’ll hire someone super junior and layer above them once we have product/market fit.’ But I don’t think that has to be the case,” says Singhal. “A strong project manager could scale alongside the organization and get more strategic.”

He saw this firsthand at Credit Karma. “Most of the initial product team were in their first or second job. About half of them struggled to keep up with the scale of the company as we hit our growth phase. They ended up transitioning out to earlier stage companies, but at far more senior roles,” says Singhal. “However, about half of the team scaled just as quickly as the organization, and still find themselves in leadership positions at Credit Karma today.”

It's hard to predict who can rise to the challenge, but those who can scale alongside the company will be your most treasured hires. I’d take these folks any day of the week over more experienced product leaders who are “lowering” themselves to take on a scrappy early-stage role.

Here are the signals he recommends watching for in interviews:

Probe if a project manager has the capacity for more.

 “Project managers are passionate about the process. Product people are passionate about the customer and how the product solves their problems,” says Singhal. To parse the difference, ask a candidate or their references to define when they’ve done an A+ job. “A candidate who's too far on the project manager side of the spectrum will only talk about how she hit the date and ensured the launch went off without a hit. But the candidate who can stretch into more strategic product work will also bring up the impact the launch had on the customer and the business.”

 “Sometimes you’ll hear ‘I'm okay getting my hands dirty for this company and your role — 

.’ For senior leaders, this either means they’re ready for early-stage and will relish in the challenge, or that they’ll tolerate the grind provided it's short,” says Singhal. “The latter puts tremendous pressure on the startup to grow. Essentially you’re in a race between the career expectations of the candidate and the growth curve of the business. To determine which one it is, ask something like ‘How would you feel if the company struggles to find product/market fit for a year and you’re still playing at a ‘lower level’?’”

Common questions from founders at this stage:

How can we tell if we have product/market fit?

After we reach it, how involved should I be as a founder in product decisions?

How big should my product team get here? What should I look for when hiring?

For the fortunate startups that manage to find product/market fit, Phase 2 is about staying heads-down on execution and introducing the right level of process.

“In this phase, it becomes less about the experiments and more about doubling down on what's working to fully capture all of the value that’s on the table. In other words, 

it’s full steam ahead — not a time to rock the boat

Finding product/market fit is like when smoke suddenly appears after you’ve been rubbing two sticks together for a long time. Now it’s all about protecting — and fanning — that feeble flame.

Founders tend to misjudge whether or not they’ve truly cleared the product/market fit bar — which Singhal argues should be set on a higher rung. “

Here’s my simple definition of product/market fit: The value of each user is greater than the cost of bringing them into the product.

 It means there are enough customers out there 

 you can efficiently bring them in,” he says.

According to Singhal, few startups that claim to have product/market fit actually reach it when defined this way — and the effects of prematurely declaring victory and jumping into rapid scaling can be disastrous. “I learned this lesson at my last startup, 

. We had the unit economics working for a few of our customers, but in reality it was a hit-driven business. We weren't able to efficiently bring in 

 of our customers profitably. If I had looked at the business holistically, I would have avoided scaling prematurely,” he says.

In other words, it’s a mistake to leave unit economics out of the product/market fit discussion. “User love isn’t enough. It’s not just about the few customers who feel passionately about your product. If you don’t 

take your CAC and LTV into account before pouring on the growth gasoline

you risk creating a situation where people like you, but it takes too much money to get them to love you

,” he says. “That approach may work in the short run, but you won’t always be able to count on cheap capital. If your business only works so long as you can keep losing money to feed it, that's a ticking time bomb.”

There are a lot of product/market fit definitions out there that focus on how many users love you. But that misses a key ingredient: the profitability and sustainability of what it takes to acquire that love.

Here are Singhal’s more specific thoughts on product/market fit challenges for consumer- and enterprise-focused startups:

, where you’re paying nearly nothing to bring in new users. This is what I was chasing when I was working on social apps like SayNow. More typical, though, is that you need to spend money to get that distribution, which becomes all the more risky if those channels dry up or if there’s not a way to earn that spend back in a reasonable window,” he says.

 “I’ve found that product/market fit can be harder to spot for enterprise. With my second company, Cast Iron, we had several paying customers and thought we’d gotten there. But I didn’t fully appreciate our product problem: The first customer’s problem was different than the second customer’s problem, which caught up with us by the tenth customer’s pain point,” he says. “If the metrics are, ‘We’ve got 10 paying customers,’ but meanwhile behind the scenes engineers are drowning in feature requests because they’re trying to solve different pain points, you don’t have product/market fit yet. You need to figure out the repeatable motion of finding users who want what you’ve built — not the ones who would pay you to build something else.”

The product has to stand on its own legs at some point — you can’t morph it for each new customer and still reasonably stake a claim to product/market fit.

After pushing past the cusp of product/market fit, founders quickly get busy with the work of shaping the rest of the company, including scaling the culture, hiring the management team and helping new functions find their footing.

“Founders can’t be in the nitty-gritty details of every product release from here on out. Meanwhile, engineering is focusing on building a more robust architecture, and marketing has something to talk about. As the team scales, each employee begins to lose context on the product and the customers. PMs are responsible for closing that gap,” says Singhal.

In other words, product’s plate just got a whole lot more crowded. “It’s a combination of defining the customer and their use cases, assessing how the current product stacks up competitively, putting together a roadmap of how it will get better, making tough calls on priorities, and ensuring everything’s getting shipped,” he says.

Here, Singhal spikes out two specific changes product teams grapple with at this stage:

. “Engineering needs to determine what to make durable. Marketing and sales need to set expectations with their customers, who need to do their own planning. So the sequence of how each release will fit together starts to become more important. Your planning horizon shifts from weeks to months because you have a better sense of what the customer wants, and you need to tell other teams where you’re going ahead of time,” says Singhal.

 “You need to start establishing more advanced communication rituals beyond weekly standups. At Credit Karma, we introduced biweekly product demos for the whole company, monthly offsites for the product team, monthly executive product reviews to actively provide that context others are seeking,” he says. “Bias towards active communication here. A company can’t hope all relevant info will passively trickle down.”

At the companies Singhal founded, he noticed a distinct cultural shift in Phase 2. “Before product/market fit, there’s a philosophy of throwing things against the wall and seeing what sticks. But when you have something that's working, you need to stabilize and deepen it,” he says. “The crazy cowboy that says, ‘Let's blow it all up and try something new,’ has to take a backseat. 

When a startup begins to scale and there’s a focus on product depth and quality, process starts to actually matter — even though process is what many came to a startup to avoid

More specifically, he finds that early-stage teams aren’t prepared for the emotional change this phase brings. “This mindset shift is psychologically challenging for everyone because most of the time it's not called out explicitly,” he says. “You start hearing things like, ‘We've lost our edge,’ or ‘Do we really need that meeting?’ It’s important to 

talk about what scaling feels like and why it’s hard

. Don’t sweep it under the rug or delay introducing the structures you need because you want to ‘move fast.’”

“I don’t really love PMs to engineers ratios — they often don’t take the specifics of your product into account,” says Singhal. “For example, teams working on end-user features tend to have a much higher ratio than a platform team. But if it helps, eight to 12 engineers per product leader is common. So if you have 25 engineers, I'd expect two to three product managers, not one or five.”

As to what he looks for in those PMs, here are the two skills that matter most in Phase 2:

A few who’ve seen the movie before. “

Half the job is figuring out what successful execution and predictable delivery looks like. You want someone to come in say, ‘We need to start setting goals, building the right communication habits and getting the right people around the table.’ Often the PM who can do that is the one who’s been at an organization that's more mature and has a stable product,” says Singhal. “Large company backgrounds can be good, because that requires lots of cross-functional work with marketing, legal and so on. But that’s not a blanket statement.”

People who know how to introduce that right level of structure.

 “Knowing what good process looks like and knowing how to introduce it to a company that doesn't have it are two entirely different skills. You need to have soft skills and a sense for how to navigate the challenges that come along with that,” says Singhal. “Most candidates coming from successful product orgs didn't create the process, they just followed it. So 

in interviews, I hunt for these skills around introducing change by asking them about a time when a process was introduced and how it went over on their team

. I want to hear answers like, ‘Let me tell you how we used to do it and how we do it now,’ or ‘We tried making this change, but it really backfired, and here’s why it went wrong.’”

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.

Common questions from product leaders at this stage: 

How do we move from an execution-oriented product team to a team that both scales and innovates?

How do we divide our attention between our flagship product and our new bets?

How do I maintain the culture while so much change is happening?

How do I build the product team and ensure accountability?

“I’ve heard a lot of founders say, ‘My product team isn’t as strategic as it should be. They’re good at getting things out the door, but they’re more like assistants to the engineering and marketing teams. I need them to come up with the next big ideas,’” says Singhal.

Just as the product mindset of Phase 1 was a mismatch for Phase 2, Phase 3 hypergrowth goals won’t be met by what you’ve already got.

“By the time scaling takes hold, a startup has built a hit product, established a user base and is ready for more. You’ve got one thing working, so the immediate question is: 

” says Singhal. “This is the phase Credit Karma was in when I joined as CPO in 2015. There were a dozen people on the product management and design team. The company had a terrific product providing free credit scores, which drove superb metrics. So the product team's job was to expand from a free score utility to the complete financial assistant on your phone.”

Hypergrowth is about scaling the core business and expanding your offerings simultaneously. Accomplishing both is insanely challenging. And it’s exponentially more difficult to pull it off amidst a sea of new employees, customers and increased expectations.

Until now, the product team has focused on delivering on the founder’s product vision while building new collaboration, communication and process muscles. “

Hypergrowth is the phase where product management truly becomes a strategic function

The company is also ready to innovate, unlike in Phase 2. “The challenge is more around picking the right opportunities to go after and creating the culture and processes to ensure new things can be built while the business scales,” he says. “Without product discipline, you might go in 50 different directions. This is where product leaders can really help the founders scale. Founders can tell you what to do immediately or they can think about the long-term company vision, but that mid-game point of how that translates several quarters out is harder. A CPO needs to be able to say, ‘This is where I see us heading in the next 12 to 24 months.’”

The faster the growth, the bigger the opportunity — and the more critical the product function becomes. Mistakes in hypergrowth all come from failing to make the transition from an important function to an essential one that drives change, innovation and scale. Here, Singhal breaks down the three most common ones:

As the company gets larger, the numbers get bigger — and harder to maintain. The exec team’s impulse will be to introduce moonshots or make splashy acquisitions. But in Singhal’s experience, the investments that need to be made in Phase 3 are far less visible and exciting.

“About a year into my time at Credit Karma, in the midst of crazy growth and exploring shiny new things, we realized that the pendulum of our focus had shifted too far away from our core business,” he says. “Though everyone wants to work on the exciting new product lines and features, we needed to make fewer new bets, invest in our organization and technical platforms, and ensure we could measure and predict our business more accurately. 

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