Non-sales founders often don't know how to evaluate or support their first sales leader. The advice is to hire a sales-focused board member or advisor whose primary role is to mentor and care for that new sales leader, providing crucial guidance and a dedicated advocate.

When revenue leaders offload hiring to HR, they lose control over the core attributes of their team. This creates inconsistent talent quality across the organization, weakening the entire sales function. The leader is responsible for the 'DNA' of their team, and abdicating this duty leads to poor performance.

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.

Transitioning from a top-performing rep requires a mindset shift from doing to enabling. A new leader's role is not to teach their specific 'Michael Jordan' method, but to align company and personal goals, then focus on removing obstacles for each team member's unique path to success.

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.

A startup's initial salesperson should prioritize mirroring the founder's successful sales approach. Their job is to deconstruct the founder's "hook" through observation and trial-and-error, not to immediately implement formal sales processes, metrics, or a CRM. Success comes from successful knowledge transfer, not premature system building.

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.

First-time leaders often feel pressure to have all the answers. Instead, they should embrace a "beginner's mind," openly admitting what they don't know. This creates a safe environment for the team to share mistakes and learn collaboratively, which is crucial for building a playbook from scratch.

A sales leader's success is determined less by personal sales ability and more by their capacity to attract a core team of proven performers who trust them. Failing to ask a leadership candidate 'who are you going to bring?' is a major oversight that leads to slow ramps, high recruiting costs, and organizational inefficiency.