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.

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.

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.

A sales leader's value isn't in managing from headquarters. It's in being on the front lines, personally engaging in the most challenging deals to figure out the winning sales motion. Only after living in the field and closing landmark deals can they effectively build a playbook and teach the team.

Early-stage recruiting requires relentless focus. Legendary investor John Doerr advised Dylan Field to think about it constantly—from morning to night—and manage it with the same discipline as a sales funnel, always feeding the top and moving candidates through the process.

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.

A powerful recruiting tactic is to ask a new customer, "Who would you have bought from if their product was better?" This question identifies competitor reps who excel at selling—persuading buyers despite product disadvantages. These individuals are prime candidates to recruit for your own team.

A holistic talent strategy requires a dual focus. An 'External Talent Cloud' provides on-demand access to specialized global skills, while an 'Internal Talent Marketplace' unlocks hidden skills within the current workforce. Operating both creates ultimate flexibility, allowing talent to flow seamlessly into and within the organization.