The informal, high-energy culture that worked for the first 15 employees began to fail as the team grew to 25-30 people. The founders learned they waited too long to formalize processes like KPIs and structured check-ins, leading to misaligned expectations and poor hires.
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Prioritizing a candidate's skills ('capacity') over their fit with the team ('chemistry') is a mistake. To scale culture successfully, focus on hiring people who will get along with their colleagues. The ability to collaborate and integrate is more critical for long-term success than a perfect resume.
As startups hire and add structure, they create a natural pull towards slower, more organized processes—a 'slowness gravity'. This is the default state. Founders must consciously and continuously fight this tendency to maintain the high-velocity iteration that led to their initial success.
Processes that work at $30M are inadequate at $45M. Leaders in hyper-growth environments (30-50% YoY) must accept that their playbooks have a short shelf-life and require constant redesign. This necessitates hiring leaders who can build for the next level, not just manage the current one.
Contradicting the common startup goal of scaling headcount, the founders now actively question how small they can keep their team. They see a direct link between adding people, increasing process, and slowing down, leveraging a small, elite team as a core part of their high-velocity strategy.
To scale from 100 to 1,000+ employees, you must stop interviewing everyone. Success depends entirely on the cultural foundation built with the first 100 people. By personally hiring and imbuing them with the company's core values, you create a group of leaders who can replicate that culture as the organization expands.
Despite success, founder Kevin Wagstaff felt like an "imposter" as the company scaled beyond $10M ARR. He recognized his strengths were in the early, scrappy "bias to action" phase, not managing a larger organization. He proactively brought in a seasoned CEO better suited for the next stage of growth.
The biggest scaling mistake is focusing on running up numbers while ignoring the underlying mindset. During its peak growth, Facebook put every new engineer through a six-week bootcamp not for immediate productivity, but to instill the company's culture. This investment in a shared mindset is what enables sustainable scaling, preventing the chaos that comes from rapid headcount growth.
As companies grow from 30 to 200 people, they naturally become slower. A CEO's critical role is to rebuild the company's operating model, deliberately balancing bottom-up culture with top-down strategic planning to regain speed and ensure everyone is aligned.
