Why Growing Companies Lose Their Edge (And How to Keep It)

In 2024, I marked my 8th year in product management. I accidentally got into it in 2016 when I co-founded an ad tech startup. I didn’t know what product management was, but my job was to lead a team of engineers to develop products that (we bet) would make buying ads on digital out-of-home screens easier. Looking back, I could have benefitted from some of the skills around discovery that I gained later. But as a technically inclined generalist co-founder, my primary concern was understanding the goals of my target customers with their out-of-home advertising campaigns and turning those insights into solutions. Wait, isn’t that what product management is?

Startup product management isn’t the product management you read about in the books. Startups must optimize for speed. Most startups aren’t flush with funds and are racing to achieve product-market fit. You must release, gather feedback, and iterate quickly, necessitating a lean process. I set up two boards: a Jira Kanban board for our project management and a Trello board for customer success operations. Customer feedback moved from the Trello board to the Jira board once prioritized for development. Most bugs were addressed when found. If something went wrong, we set up a call to resolve it immediately. No need to wait for the sprint to finish or to schedule a retro. Everyone talked to customers and understood design. We had three engineers, each on a different product. We were efficient. Building 0 to 1 with a small, focused team, motivated to win before running out of runway, does indeed make for a well-oiled product team.

So why doesn’t this mindset persist as companies grow?

As companies grow, they face a paradox. The systems to manage scale often become barriers to maintaining startup agility. I have seen this transformation happen multiple times, and it is both fascinating and frustrating.

Take a typical Series A startup hitting its stride. Suddenly, there's pressure to "professionalize" operations. Investors want to see mature processes. The leadership team starts hiring experienced managers from big tech. These managers bring with them the processes that worked at Google, Amazon, or Microsoft. But here's the thing - those processes were designed for companies managing thousands of engineers and dozens of product lines, not for a company with a hundred people trying to maintain its edge.

At first, the mindset shift is subtle. Product managers start spending more time in planning meetings than talking to customers. Engineers get siloed into specific teams with rigid boundaries. The rapid customer feedback loop that drove early success gets replaced by quarterly OKRs and formal user research studies. It's not that these practices are inherently bad - they're just often implemented without considering the context.

I've worked in both environments. I'll tell you this: maintaining startup-style agility in a growing company isn't about avoiding process altogether. It's about being intentional about which processes you adopt and why. Product managers should keep customer feedback loops tight even as the company scales. How? Spend at least 20% of your time talking to customers and maintain small, cross-functional teams with end-to-end ownership. As far as a mindset, question any new process that doesn't directly contribute to building better products.

Companies that scale while maintaining agility share a common trait: they treat process as a tool, not a solution. They understand the goal isn't to implement "best practices" but to maintain conditions that allow teams to move fast and focus on solving real customer problems.

While product management looks different everywhere, maybe the real question isn't why we lose that startup mindset as we grow. Instead, the real question is how can we intentionally preserve the elements that made us successful in the first place? After all, the core of product management remains the same whether you're three people or three thousand: solve your customers' problems fast enough to matter.