Ready to build your own Founder-Led Growth engine? Book a Strategy Call
Frontlines.io | Where B2B Founders Talk GTM.
Strategic Communications Advisory For Visionary Founders
20 HR Tech Founders
Product-Market Fit Lessons
Separate the Data From the Story You've Been Telling
When Karoli Hindriks saw the signals that Jobbatical needed to pivot, she didn’t act on them for nearly a year. The data was clear. What held her back was the weight of the narrative she had built around the original vision. “I think as a founder, it was kind of this thing that you have convinced your investors, you have convinced yourself, you have convinced your employees, your team, basically the media, how you’re changing the world, and now you’re going to set that aside.” The sunk cost wasn’t financial. It was psychological. “It took me about nine months just to get over the feeling like it is a failure if I actually decide to pivot.” What finally broke the stalemate was reframing what investors actually expect: “Every VC or angel investor invests in you. They don’t expect everything to be linear and just going by the book. I think only 20% of the companies they invest in end up doing what they started.”
Validate PMF by Seeing Whether Someone Else Can Close the Deal
Most founders measure product-market fit through retention curves or customer surveys. Mike Fitzsimmons added another signal: whether another person could close the deal. He treated the transition away from founder-led sales as “a great litmus test on what kind of product market fit you have,” with a clear pass/fail condition: “if you can’t get someone else to sell it as well as you sold it, then you probably don’t have the fit that you hoped you had.” When the motion couldn’t be replicated, Mike traced the problem back to the product or the message: “if it’s too complicated where you can’t replicate that sales motion.”
Extend Your PMF Measurement to Every Person the Product Touches
Prem discovered one of his strongest product-market fit signals from people who weren’t even customers. “One of the things that surprised me the most, we would have hiring teams that were in a good way really focused on candidate experience, which is awesome. But when we talk to candidates, one thing that surprised me is we have our tool, the candidates can rate their experience engaging with Humanly. And even the candidates that didn’t get the job rated it very strongly, which was a surprise.” By the time Humanly hit scale, the signal had compounded: “We passed a million candidates that we’ve engaged with and the average rating they have of the experience is about 4.8 out of 5.” For operators building products that serve two sides of a transaction, satisfaction from the non-paying side can be one of the most honest indicators that the product is actually working.
Use Referral Behavior and NPS to Identify the Segment Worth Doubling Down On
When Gusto was still early, Tomer used a specific cluster of behavioral signals to identify where the product had genuine traction and where to concentrate resources. The diagnostic had nothing to do with revenue. He looked for: “Where are the high NPS customers? Where are the customers that just can’t stop referring you? Who are the people who just rave about you on social media on their own without you trying to find them? Right? Where do you have customers just coming in without you even knowing how necessarily they heard about you?” Once those signals pointed clearly at a segment, Tomer’s direction was to stay there: “Those industries, those segments, those sizes, that demographic is where you want to double down on again and again, honestly, for several years at least, until you get to like 10 million ARR or something like that.” Customers who refer without being asked and promote without being prompted are telling you something that revenue alone cannot.
Assess Whether the Enabling Technology Exists Before Building the Product
Siadhal and his co-founder identified their core problem in 2018, but they were clear-eyed about the technology gap they were working against. “In a funny way, we were probably a little bit early in identifying the problem in 2018 because the solution wasn’t actually quite ready. The solution wasn’t possible.” Their timing heuristic was deliberate: “we think it might be barely possible to solve this problem. And if that’s the case, it’s probably the right time to start the company.” The product improved incrementally until the enabling technology caught up. “Since late 2022, with LLMs being incredibly powerful and accessible for companies like ours, we’ve really been able to change the solution. Well, frankly, just make the solution a ton more powerful and actually highly valuable for our customers.” The lesson is that problem clarity is necessary but not sufficient. The right time to build is when the solution crosses from impossible to barely possible.
Follow the Customer's Problem Even When It Redirects Your Roadmap
Benivo’s real market opportunity did not come from internal product planning. It came from listening carefully in a sales meeting. When Nitzan showed Google what he had built, their response was direct: “yeah, that’s nice, but we have a different problem. We have a problem with employees who need to relocate, with getting payments to them, and everyone in the industry says it’s impossible to do.” Rather than defending his existing product, Nitzan asked what they needed. “We said, what do you need to do? And they explained to us the challenge.” He recognized his existing technology could address it, committed on the spot, and followed the customer’s problem into territory the rest of the industry had walked away from.
Test Whether Your Product Solves a Durable Problem or Rides a Trend
When the hiring market and DEI budgets tightened simultaneously in early 2023, Charlotte had a clear-eyed read on what it meant. “As we entered into early 2023, we started to see, okay, the hiring market is turbulent, the DEI market is turbulent. And we need to figure out how we can actually make a sustainable impact over time that’s not reliant on strategies that will ebb and flow.” The product wasn’t broken, but its market relevance was tied to conditions outside her control. That realization drove the pivot decision. “The best go to market decision that my co founder and I made was how do we accelerate and expand the application of this platform so that it’s a must have and not a nice to have?”
Wait for Customers to Pull You Forward Before Declaring Product-Market Fit
Sid didn’t call product-market fit based on internal enthusiasm or investor pressure. He saw a specific signal: customers repeatedly asking for more. As he described it, “it really came down to where customers were taking us and where the teams just saw so much more opportunity. Capital was the constraint. The team and our time was the constraint. We were having so many conversations with customers about, hey, can you help me with this challenge, beyond hiring? And we just kept hearing this pattern again and again.” That repetition across conversations was what moved the needle. “That’s really what gave us a lot of confidence to say, wow, customers are saying this, the team is saying this. We have such an incredible potential, and we’re not fulfilling it simply because of this constraint.” The signal was the market pulling harder than the team could keep up with.
Start With True Believers and Use Their Success to Pull the Market In
When creating a new category, not every prospect will understand the value right away, and Ben was direct about accepting that reality. “Early on you have just true believers who are your customers that get it right away. And then there’s honestly a bunch of folks that don’t get it. And that’s okay. Not everyone’s going to get it right away.” The mistake is burning energy trying to convert skeptics before you’ve built the proof. Instead, Ben described the only path that actually moves the market: “You actually have to deliver a tremendous amount of value to the market, to your early customers, and magnify their successes to validate why other folks should spend their time and attention investing in what you do.”
Sell the Vision First When the Market Has Never Seen Your Solution
Wingspan’s earliest B2B customers weren’t responding to a polished sales pitch. They were signing up because they shared Anthony’s view of where the market was heading. “Earlier in our journey, the companies that were signing up were buying into our long term vision because we saw the world differently and they bought into that vision,” he said. That belief wasn’t abstract. Those customers stayed, expanded, and were willing to share their stories publicly because the product was delivering real outcomes. “We are saving them hundreds of thousands of dollars transforming their business and we’re providing a much better experience for their workforce, which is really a high priority.” When early customers align with the vision and the results follow, that combination is worth paying close attention to.
Identify the One Customer Win That Proves Your Approach Works
Before Paraform raised its seed round, John Kim wasn’t focused on fundraising at all. The signal that changed everything was a single customer result. A fast-growing startup had been struggling to fill a critical engineering leadership role for eight months, “and not because they were doing something wrong. It was just an incredibly hard role to recruit for.” Paraform filled it in two months, over the holidays. As John put it, “I think it was a testament to what our marketplace could do for our customers.” That one outcome became the proof point that attracted their lead investor, and it illustrates a principle worth internalizing: one undeniable win for the right customer, in the right conditions, can tell you more about whether your model works than months of aggregate data.
Find the Use Case That Repeats Before You Productize It
Before Hanns built a scalable product, he spent six years running consulting projects inside enterprise HR departments. “In 2020, we actually decided to pivot because we then had enough knowledge of what the industry, especially the HR industry, was looking for in terms of skills management, skills platform, skills data management.” The pattern he was looking for was a use case that showed up repeatedly across different customers. He found it: “we did actually see that use case quite often, or where we found that use case that was replicable, which was the situation of internal career transparency for employees.” Founders who spend real time inside customer problems before committing to a product architecture reduce the risk of building something that needs to be rebuilt from scratch.
Move Faster When External Events Create Sudden Urgency for Your Product
Jennifer Dulski built Rising Team to solve a problem she had carried throughout her entire career as a leader. As she described it, “I built this because it was the tool I wish I had as a leader of teams throughout my career. I always wanted something like this, and it never existed.” Then the market shifted beneath her in a matter of weeks. The pandemic turned a chronic problem into an acute one, and as Jennifer put it, “the thing that I thought was important overnight became urgent to everybody because building more connected, engaged teams, you know, when everyone’s team was remote, all of a sudden everyone really needed a way to help them do that.” When external events compress the timeline from awareness to urgency, the window to move is short and the operators who recognize it early are the ones who capitalize.
Measure PMF Through End-User Engagement After the Sale Closes
When your buyer and your end user are different people, the sale closing is only the starting point. Dirk Doebler described tracking employee usage as the core success metric: “We view that as both one, our company is purchasing this, but then ultimately are the employees using it. And our driving star is the employee we’re selling to the company.” The numbers backed it up: “We see over two thirds of parents who are having a kid using our support program, which is huge. And then when they do, they’re using about 13 hours of support on average.” “We have a very high adoption rate within sort of overall category of what we’re doing. We’re really proud of that because we’re clearly showing that we add so much value to these employees’ lives.”
Announce Before You Build to Validate Real Demand
Before Remote had a product, Marcelo and his co-founder published a simple blog post announcing what they were building. The response was immediate. “I remember that we had this massive influx of people wanting to buy from us.” Buyers were reaching out before anything existed to buy. As Marcelo put it, “We knew for a fact that was hit. It was going to be a hit because of the demand and the need of the people reaching out to us even before we launched the company.” Unsolicited inbound before you have anything to sell is one of the cleanest PMF signals available to a founder.
Track Customer Retention as Your Earliest PMF Signal
Matt Pierce pointed to zero customer churn as one of the clearest signs that his product was delivering real value. “To date, knock on wood, we haven’t lost a single customer. So hundreds and hundreds of customers. We haven’t lost a single customer.” In a market where HR and payroll buyers carry scar tissue from painful software rollouts, that record carried weight. As Matt put it, “none of them have left to go to competitors or left just to turn it off, which means we’re doing a really good job of taking care of our customers and ultimately our end users.” Retention, not just new logo growth, was the signal he pointed to when assessing whether the business was working.
Run a Small Experiment Before Committing to the Full Build
Before Andela had a real product, a sales team, or any formal infrastructure, Jeremy and his co-founders ran a simple test to see if their core thesis held up. They went looking for 20 people for their first cohort and “ended up with 240.” Of those, “42 were amongst the top 2% most gifted people on the planet, just in terms of aptitude and problem solving ability.” That single data point was enough. The team looked at each other and said, “this is clearly a thing we need to explore.” Six people spread across three countries then stepped back and agreed: “this is real, and the world needs something like it.” The experiment didn’t prove the whole business, but it proved enough to move forward with conviction, which is all early validation needs to do.
Listen for the Gap Before You Start Building
Before Guideline had a product, Kevin already had his answer from the market. “Everybody we talked to was like, this doesn’t exist, please make this.” That consistent, unprompted pull gave the founding team something more valuable than a survey or a pilot: genuine conviction going into an 18-month build and a difficult fundraising period. Kevin and his co-founders leaned into that signal hard. “We had a lot of conviction that it was the right product. They were really excited about it. I was really excited about it.” When they finally shipped, the signal proved out. “Luckily for us, we’re right and we got product market fit day one, which was great.” The lesson isn’t that they got lucky. It’s that they did the talking before they did the building, and the market told them exactly what it needed.
Watch for End User Referrals as a Signal That the Product Has Real Pull
Sapia saw an organic dynamic emerge from its end users that translated directly into enterprise pipeline. “Every week we’ve got about 100,000 candidates engaging with our chat and people love the fact that it feels really comfortable and easy, but they also love the learning and coaching they get. And so there’s this virality that naturally comes from the candidate experience that’s really led to deals.” The referrals weren’t coming through formal channels or prompting from the sales team. “We’ve had a whole number of deals that have come from candidates loving the experience, telling their mum or dad, brother or sister, who happen to be someone that’s quite senior in a TA role, in a talent acquisition role, in an HR role.” Barb described this as one of the key GTM motions that drove opportunities for the company.
Dig Into Unexpected User Behavior to Find a Stronger Market Opportunity
Fetcher’s real market revealed itself through behavior the team hadn’t anticipated. Andres and his co-founder were building a consumer product when they noticed something worth paying attention to: “recruiters were using a product that we were building more for consumers.” Rather than treating it as noise, they followed the signal. As Andres described it, “when we started really digging into what was happening, they talked to us about a problem that we actually knew that existed, but weren’t paying necessarily too much attention to it.” That conversation surfaced a market opportunity that had been sitting in plain sight, hiding behind a product that was pointed at the wrong audience.