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How StackAdapt Spent Four Years Finding Product-Market Fit Despite Knowing the Customer Problem

Understanding the problem doesn’t equal knowing how to profitably acquire customers at scale.

In a recent episode of Unicorn Builders, Vitaly Pecherskiy, CEO and Co-Founder of StackAdapt, broke down the mechanics of his programmatic advertising platform’s decade-long journey. Despite leaving industry jobs specifically because they felt the pain firsthand, it took four years to reach true product-market fit. Today, StackAdapt operates with 1,600 people across 20 markets—but the path from three founders in a kitchen to global scale revealed stark realities about what “boiling the ocean” actually means.

What “Boiling the Ocean” Actually Looks Like

StackAdapt launched in 2014 with domain expertise. Vitaly and one co-founder had worked in programmatic advertising. They left specifically to build the next-generation platform. The problem was validated.

But validated problems don’t reveal which acquisition channels work, what retention economics look like, or how to structure teams around business drivers.

“Even though we understood the problem, surprisingly, that doesn’t automatically mean you have a product market fit,” Vitaly explains. “Those first few years, even though we knew exactly what we actually want to do, it was still, you know, I would call it boiling the ocean.”

The variables StackAdapt had to solve simultaneously: customer acquisition channels that worked predictably, unit economics that scaled profitably, retention mechanisms that actually retained, and organizational design that matched their business model. Each variable affected the others. Testing meant iterating through combinations until the system worked as a whole.

Product-market fit arrived in 2018 when StackAdapt became profitable with clear answers: “We understood, oh, we know exactly what’s the profile of our customer, we can reliably find more of them,” Vitaly says. They had mapped acquisition costs, retention patterns, and the financial model that would scale. That clarity—not just product-customer fit—marked true product-market fit.

Receivables as a CEO-Level Function

Before 2018, StackAdapt faced an operational reality that exposed a gap in how most founders think about revenue.

Vitaly describes the moment: “Our credit cards are maxed, we have no cash on the bank account, our payroll is hitting like in two days. And I was like, what are we gonna do?”

The receivables existed. The deals were closed. The revenue was booked. But none of that mattered with payroll due in 48 hours.

“Pick up the phone, start calling customers and saying like, we need to collect today. Like please wire us the money. And surprisingly it worked.”

The lesson wasn’t about crisis management—it was about misunderstanding where the business model actually closes. “That was the first lesson in, you know, let’s make sure that we’re good at not just closing business, actually collecting the money, because at the end of the day, that’s the lifeblood of running the business.”

The operational implication: payment terms, collection processes, and DSO tracking deserve the same rigor as pipeline management. ARR means nothing if cash doesn’t arrive before payroll is due. For early-stage companies operating on thin margins, the gap between booking revenue and collecting cash can determine survival.

Building a Hot Buttons Framework for Durable Messaging

Once StackAdapt gained traction, they systematized what made prospects engage.

“We came up with this idea, hot buttons, random term,” Vitaly explains. “But essentially we just said like, what are the things that really resonate with our customers? And I think we made a list of, I don’t know, 8 or 10.”

The framework identified specific themes that consistently triggered customer interest. Not value propositions or feature sets—the specific pain points and trigger events that made prospects lean in during conversations.

The discipline came in execution: “We just built all our sales playbooks, all our marketing message around it, and we just continue hammering that messaging basically for years because, like a lot of themes that we identified back in like 2015, 16, they’re still relevant.”

While competitors chased quarterly messaging refreshes, StackAdapt maintained focus on 8-10 core themes for years. The insight: customer pain points in mature markets change slowly. The impulse to refresh messaging quarterly often stems from internal boredom, not market evolution.

The implementation approach requires documenting patterns systematically: which questions prospects ask unprompted, which competitive positioning triggers engagement, what makes deals accelerate. The hot buttons list becomes the foundation for sales enablement, marketing campaigns, and product positioning—creating organizational alignment around validated customer triggers.

The 2016 Bet on Internal Creative Capacity

At 50-60 people in 2016, StackAdapt hired a full-time videographer.

“This was like 2016. This is way before a lot of the, you know, the trends today,” Vitaly notes. The role captured behind-the-scenes footage, customer stories, and marketing content—years before video became standard in B2B.

The decision reflected a broader philosophy about building versus buying capabilities: “We always wanted to have as many resources internally that we can really get them on the speed as to like what are we trying to accomplish as a company so they deeply understand our problem, deeply understand our customer, our team and we can connect them in like very fast.”

The tradeoff was deliberate: higher upfront costs and overhead in exchange for speed, institutional knowledge, and the ability to iterate without external dependencies. Today, StackAdapt operates a creative studio team that serves both customer needs and internal marketing—a capability that compounds over time as the team develops deep product and customer understanding.

The pattern extended beyond creative: StackAdapt builds capabilities in-house that competitors outsource. “Even with our product today, everything is built from ground up. We’re trying to build as many capacities as a team, as a company internally so we can innovate, move really fast.”

The strategic question for founders: which capabilities will become sustained competitive advantages? Those justify the premium of internal ownership over the efficiency of outsourcing.

Execution Depth Over Opportunity Breadth

After reaching profitability in 2018, StackAdapt had the validated PMF that most startups chase. The temptation at that stage: explore adjacent segments, test new product lines, experiment with different go-to-market motions.

Vitaly took the opposite approach: “Once you have product market fit in a large enough total addressable market, you just need to hammer that product market fit until it stops working.”

From 2018 forward, StackAdapt’s strategy was disciplined execution on a proven model. “In many ways since 2018 we’ve been doing the same thing, just at a greater sophistication, greater scale.”

This wasn’t stagnation. Sophistication increased continuously—better systems, deeper product capabilities, more refined targeting. But the core motion remained constant. The constraint in a large TAM is rarely opportunity breadth. It’s execution depth: how well you can repeatedly execute a proven playbook while maintaining quality as you scale.

The approach unlocked StackAdapt’s COVID-era expansion. In 2020, they had 170 people in one Toronto office. The pandemic created a forcing function: “We’re stuck at home, we’re fully virtual, let’s go global.”

Between 2020 and 2023, headcount grew from 170 to 900, eventually reaching 1,600 across 20 markets. The foundation for that scale was the years spent hammering one proven motion rather than spreading attention across multiple experiments.

What Technical Leadership Means at 1,600 People

Two years ago, Vitaly moved from COO to CEO. The transition forced a reckoning with what effective leadership looks like at scale.

“The biggest insight for me was like maybe after my first year or like maybe six months into the job that I was like, well wait a second, I don’t need to play a role of a CEO, I just need to be the CEO. And the only job I have is building a successful business long term.”

At 1,600 people, Vitaly maintains that leaders must remain technical enough to match individual contributors in their domains. “As long as leaders understand how critical parts of our company function, like with their respective domain, they can go down to individual contributor level and go toe toe with them. Like that’s super important.”

This isn’t about micromanagement. It’s about decision-making grounded in operational reality rather than abstraction. Vitaly acknowledges the impossibility of total knowledge: “I will lie to you if I say I know everything about how our company works. There’s just so much.”

But leaders must understand how critical systems function at the implementation level. The alternative disconnects leadership from where value is created: “If you’re living in a culture where it’s very, you know, you essentially, I don’t know, as a leader sitting in a high chair, trying to just order people around, like, how do you know what’s grounded into like the reality?”

Vitaly still personally joins customer calls. He stays connected to where “rubber meets the road.” The practical standard: can you review a customer call, dissect unit economics, or debug a critical system alongside your team? That level of technical engagement maintains credibility and ensures decisions reflect operational constraints, not wishful thinking.

Customer Data as Input, Not Directive

StackAdapt runs annual in-depth customer surveys that require weeks to digest. But Vitaly draws a distinction between collecting data and blindly following it.

“Even if it’s perfectly represented, you know, doesn’t automatically mean that you should do everything that your customers tell you to do,” he explains.

The framework for processing customer feedback requires triangulation: Does it align with strategic vision? Are you best positioned to solve this problem? Is feedback coming from target customers or edge cases?

Some validated data gets intentionally shelved. “You look at data and you’re like, that’s interesting, let’s shelve it.”

The balance matters because customer feedback reflects current pain points, not future market position. Large customers request features that serve their specific use case but may not generalize. Small customers suggest improvements that don’t justify development cost. Representative data can still point in the wrong strategic direction.

The practical discipline: build systematic feedback mechanisms while developing the judgment to know when perfect data should be ignored. Customer input informs direction but doesn’t determine it. The business model, competitive positioning, and long-term vision provide the framework for interpreting what customers say they want.

The Compounding Phase

After a decade of building, Vitaly’s perspective on scale has shifted. “In my head, like I said, I feel that we’re tiny compared to the, the opportunity in front of us.”

His strategy going forward: “Go harder. Only way is harder. This is a time to double down.”

The early years required constant effort to prevent momentum from reversing. “In earlier days, it’s just so hard where everything is just like, if you’re not constantly pushing this boulder up the mountain, like, it’s just gonna crush you.”

Now the dynamics have changed. “Now there’s some real momentum and the brand and the product and the team is like, it’s all compounding,” Vitaly says.

The worst strategic error at this stage would be complacency: “I think the worst thing we could do is get comfortable.” StackAdapt operates with the recognition that reaching scale doesn’t justify coasting. The opportunity ahead remains larger than what’s been captured.

For founders navigating similar trajectories, StackAdapt’s path illustrates a specific pattern: expect years of grinding before product-market fit crystallizes, then hammer that PMF relentlessly when you find it. The constraint in large markets is rarely lack of opportunity—it’s the discipline to execute one proven motion with increasing sophistication rather than fragmenting attention across multiple experiments.