Since leaving his post as Credit Karma’s Chief Product Officer this past summer, Nikhyl Singhal 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 will 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 finding product-market fit and hiring your first PM, to the “teenage years” of optimizing products in the messy middle and growing to a 10-person product org, 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 holding onto their product Lego. 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.)
- Phase 1: “Drunken walk." 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.
- Phase 2: Product-market fit. 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.
- Phase 3: Hypergrowth. 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.
- Phase 4: Scale. 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.
Phase 1: Take a "drunken walk"
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?
What this stage looks like:
“My friend Dave Whorton 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 stage 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.”
In short, product management is essentially project management 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.
Mistakes that are easy to make:
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:
- Too early: “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.”
- Too late: “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.”
Who to hire:
“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.”
- Listen for this phrase. “Sometimes you’ll hear ‘I'm okay getting my hands dirty for this company and your role — for now.’ 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’?’”
Phase 2: Reaching product-market fit
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?
What this stage looks like:
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,” says Singhal.
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.
How to tell when you get here:
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 and 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, SayNow. 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 all 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:
- Consumer: “The obvious sign is a viral growth loop, 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.
- Enterprise: “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.
The role of product vs. the role of the founders:
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:
- Roadmaps. “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.
- Communication challenges: “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.”
Mistakes that are easy to make:
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.’”
Who to hire:
“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.
Phase 3: Kicking into hypergrowth
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?
What this stage looks like:
“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.
Here’s what’s going on: 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: What’s next?” 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.
The role of product vs. the role of the founders:
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,” Singhal says.
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.’”
Mistakes that are easy to make:
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:
1. Neglecting the core business.
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. Strengthening cross-functional teams, processes and foundation isn’t sexy, but it’s key to innovation.”
2. Failing to change culture.
Innovation can’t be achieved without introducing change. “'When hypergrowth hits, you need both the managers who can keep things going and entrepreneurs who can go zero to one on new bets. But creating a homogenous product org that can balance all of that is really hard,” says Singhal. “Existing employees fear changing things that are working. In contrast, newly hired employees are all about change. Yet they have little trust, don’t know the twists and turns of how things are done yet.”
To ease the transition, Singhal recommends cementing change as part of the culture. “Turn change into a value. Celebrate and plan for change, making it expected and normal, something everyone is going through,” he says.
Here are two quick tactics he relied on:
- Schedule your reorgs like a yearly checkup. “The idea that our team would be structured the same at 15 versus 30 employees was silly, but any reorg triggers fear. So we thought it was better to have everyone plan for it annually and participate in how it’s shaped.”
- Review your team’s challenges every six months. “We’d always review our list of challenges and compare them to the past six months. Though they were always long, they were also always different,” says Singhal. “This helped drive home the message that the challenges of the moment are often overcome with time and hard work.”
People feel the problems of today are the problems that are here to stay. Your job is to show that’s not the case. Do all that you can to help your team find their startup sealegs and get used to the currents of constant change.
3. Staying too deep in the weeds.
“As the product line grows from one to many, it's increasingly difficult for the CPO to have clear visibility. Just as the founder’s role changes, so does the product leader. Your team becomes your product,” says Singhal.
“The biggest challenge is that you got elevated to this role because you’re good at understanding how to machine product. Now you need to create space, empower others and let go — and avoid becoming a seagull manager. Carefully examine, for example, how your organization reviews and approves product changes. It’s a balance between creating enough autonomy while ensuring the product is cohesive and surprises are avoided,” he says. “At Credit Karma, I think we experimented with a half dozen approaches, from exec reviews on all significant changes to no reviews at all. And eventually, we landed on monthly business reviews with a broader audience, and product reviews in smaller forums.”
CPOs, don’t be a seagull — the kind of leader that flies in, makes a lot of noise, dumps on everyone, then flies out.
Who to hire:
“People join during hypergrowth so they can grow faster than they would at a startup or scaled company — but that doesn’t happen automatically,” says Singhal. “You have to consciously engineer opportunities for individuals to grow as quickly as the company does while also looking for the new folks who will add that innovator’s blood so you can successfully pivot into new areas.”
Here are the three hiring rules he recommends leaning on in Phase 3 to get that balance right:
1. Look for entrepreneurs at scale.
“The new folks you fold in need to be excited and comfortable working at a larger setting. A profile that works well is someone who’s done stints at large-scale companies as well as scrappy startups. You need folks who can hold both playbooks in their head,” says Singhal.
“In my experience at Credit Karma, the people who hadn’t done the zero to one stage struggled to connect with the founders and their scrappy, no process instincts. And in contrast, without experience at scale, new hires would get frustrated with all of the stakeholders, the pace of change and number of projects occurring in parallel. Often people who were previously founders or who played sizable founding team roles are a good fit.”
2. Power up your internal talent pool.
Ensure internal candidates have better opportunities than outsiders. “With lots of unfilled headcount, it’s tempting to take your best roles and use them to bring in great talent. However, this sends a signal to the existing team that there are fewer growth opportunities,” says Singhal. “To ensure you’re growing and retaining your best talent, consider slowing down hiring, raising the quality bar and using the time to identify your top talent and formally craft their career plans at the company. Just the act of seeing where your staff might go in a year or two can dramatically alter your hiring plan and improve retention.”
This especially applies to senior leaders in the team. “If the role of the senior leader is more of a go-between the levels, that’s not very appealing. Seasoned product directors want to carve out an area of ownership. Many of them could head up product on their own at smaller companies yet choose to join us,” says Singhal. “To win those candidates over, ensure the team is grouped into sub-organizations that can be owned independently. Your job as CPO now shifts from running these orgs to ensuring the product team is coordinated and cohesive.”
3. Remember that it’s not a “pipeline problem."
Half of those on the 75-person product management and design team Singhal built out at Credit Karma were women, which is unusual in product circles. “It wasn’t a choice — to build the best product for our diverse member base, we needed a diverse team. And we didn’t get it done by throwing our values up on the website or asking ‘Do you know any women looking for a role?” he says. "You need to challenge yourself and your team to do more, otherwise you’re hiring pipeline has no hope of being balanced. How many coaching or mentoring meetings do you take with the type of people you are trying to recruit so you can better understand their perspective? What are you signaling to your team about how much diversity initiatives matter?"
Here's a quick preview of the tactics Singhal did lean on:
- “Start with the culture on your existing team before you look to bring more people through the door. We often jump straight into recruiting to boost diversity and underindex on inclusion as a result. I spent a lot of my time trying to cultivate a safe environment where we could embrace our differences and truly share our perspectives. As a small example, at our staff meeting every month, we had a group discussion section where we tackled topics such as grappling with imposter syndrome and the challenges of being an underrepresented minority at work,” says Singhal. “This open discussion allowed folks to practice listening and learning from everyone’s experiences, and hopefully reinforced that belonging was important.”
- “In parallel, the entire team, including myself, met with dozens of people each quarter from diverse groups we wanted to see represented in the company. The goal of these meetings was not to recruit, but to listen. Understanding what these future candidates would look for helped us fine tune the culture. And it signalled to everyone our genuine interest in building a diverse team.”
- “We reviewed interview feedback on candidates live as a group. It was a big investment of time, but it flagged unconscious bias and made it conscious. And it gave me an opportunity to enforce the value of a balanced team nearly every day.”
Starting to address diversity by focusing on recruiting is like fixing the quality of the product by improving your testing process. Testing won’t fix a broken product, just as recruiting won’t fix a broken environment.
IN SUMMARY:
Understanding the different phases of a product org is key to hire effective product leaders. "You need to right-size the product team for the challenges the company faces. At the risk of repeating myself one too many times what got you here won’t get you there — too many startups don’t learn this lesson," says Singhal.
“In the end, great product management is all about adding value through people and collaboration. You have to adjust to the founders and culture, help scale what’s working, change what’s not, and push for innovation when the company is most ready and willing."
Photography by Bonnie Rae Mills.