Founders often chase executives from successful scaled companies. However, these execs can fail because their experience makes them overly critical and resistant to the painful, hands-on work required at an early stage. The right hire is often someone a few layers down from the star executive.
Related Insights
Figma's founder, Dylan Field, admits he was a poor manager initially. His solution was to hire experienced leaders he could learn from directly, like his first director of engineering. This flips the traditional hiring dynamic; instead of hiring subordinates, insecure founders should hire mentors who can teach them essential skills and push the company forward.
Before hiring for a critical function, founders should do the job themselves, even if they aren't experts. The goal isn't mastery, but to deeply understand the role's challenges. This experience is crucial for setting a high hiring bar and being able to accurately assess if a candidate will truly up-level the team.
Resist hiring quickly after finding traction. Instead, 'hire painfully slowly' and assemble an initial 'MVP Crew' — a small, self-sufficient team with all skills needed to build, market, and sell the product end-to-end. This establishes a core DNA of speed and execution before scaling.
At the $1-10M ARR stage, avoid junior reps or VPs from large companies. The ideal first hire can "cosplay a founder"—they sell the vision, craft creative deals, and build trust without a playbook. Consider former founders or deep product experts, even with no formal sales experience.
Before hiring for a critical function like growth marketing, Gamma's CEO spent 6-12 months doing the job himself. This immersion taught him what "great" looks like, preventing a bad hire and ensuring he could properly lead the function he was delegating.
Aravind Srinivas intentionally avoids hiring candidates with established track records from large tech companies. He believes people hungry for their first major success are more motivated and better suited for a startup's intensity than those who may be less driven after a previous big win.
Early-stage companies need experienced executives not just for their skills, but for their 'borrowed credibility.' A well-respected leader like former CEO Bob Muglia lent Snowflake instant legitimacy, which inspired belief in the team, reassured customers, and empowered the young founders.
The "CEO of the product" role at a large company involves managing the inertia of an already successful product. This is fundamentally different from founding, which requires creating value from nothing with no existing momentum. The skill sets are deceptively dissimilar.
