When evaluating sales leaders, prioritize their track record in recruiting above all else. Exceptional leaders are talent magnets who build scalable teams through strong hiring and enablement. Their ability to attract A-players is the foundation of a predictable revenue machine.
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.
Treat hiring as a compounding flywheel. A new employee should not only be a great contributor but also make the company more attractive to future A-players, whether through their network, reputation, or interview presence. This focus on recruiting potential ensures talent density increases over time.
Success is often attributed not to a relentless personal grind, but to a superpower in attracting and retaining top talent. True scaling and outsized impact come from empowering a great team, embodying the idea that "greatness is in the agency of others."
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 most promising hires are often high-agency individuals constrained by their current environment—'caged animals' who need to be unleashed. Look for candidates who could achieve significantly more if not for their team or organization's limitations. This is a powerful signal of untapped potential and resourcefulness.
Over a long career, great leaders accumulate a "snowball of talent"—A-players who follow them from one venture to the next. This becomes a powerful litmus test when hiring executives: if they have no network of past colleagues eager to join them, it's a major red flag about their leadership ability or the quality of their past teams.
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.
Don't hire more reps until your current team hits its productivity target (e.g., generating 3x their OTE). Scaling headcount before proving the unit economics of your sales motion is a recipe for inefficient growth, missed forecasts, and a bloated cost structure.
A sales organization has truly scaled when leadership stops talking about individual deals and starts managing based on predictable capacity. This means knowing that a certain number of ramped sellers will predictably generate a specific amount of revenue each quarter, turning sales into a machine.