Don't confuse the roles of an Executive Assistant (EA) and a Chief of Staff (CoS). A CoS is typically a future founder with high 'slope' hired for a 1-2 year tour of duty to solve complex problems. An EA is a career caretaker hired for a decade-long relationship where trust and intimacy compound over time.
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A16z's foundational belief is that founders, not hired "professional CEOs," should lead their companies long-term. The firm is structured as a network of specialists to provide founders with the knowledge and connections they lack, enabling them to grow into the CEO role and succeed.
Simply hiring superstar "Galacticos" is an ineffective team-building strategy. A successful AI team requires a deliberate mix of three archetypes: visionaries who set direction, rigorous executors who ship product, and social "glue" who maintain team cohesion and morale.
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.
Organizational success depends less on high-profile 'superstars' and more on 'Sherpas'—generous, energetic team players who handle the essential, often invisible, support work. When hiring, actively screen for generosity and positive energy, as these are the people who enable collective achievement.
The difference between a true partner and an employee is whether you seek their counsel on complex problems. If you consistently go to them for advice when you're unsure, they're a partner. If you only give them direction, they are not a "thought partner," which is a red flag for a C-level executive role.
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.
Unlike a functional manager who can develop junior talent, a CEO lacks the domain expertise to coach their entire executive team (e.g., CFO, VP of HR). A CEO's time is better spent hiring world-class leaders who provide 'managerial leverage' by bringing new ideas and driving their function forward, rather than trying to fix people in roles they've never done.
The founder hired an experienced CEO and then rotated through leadership roles in different departments (brand, product, tech). This created a self-designed, high-stakes apprenticeship, allowing him to learn every facet of the business from experts before confidently retaking the CEO role.
