New SDRs get overwhelmed when forced to learn industry nuances first. A better approach is to prioritize mechanics (CRM, scripts), then knowledge (personas), and finally the 'art' of sales, which develops over time. This builds confidence and allows them to execute quickly while they learn.

In the pre-product-market fit stage (the first ~20 deals), the sales leader's primary role is not just closing revenue, but acting as a product manager. They must be in every meeting to gather objections, find pockets of value, and translate raw market feedback into actionable insights for the engineering team.

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.

New salespeople lack personal success stories to use as social proof. Leaders must proactively provide them with a library of stories about other clients or team members. These 'borrowed' narratives are essential for building a value bridge with early prospects.

A founder's ability to sell is not proof of a scalable business. The real litmus test for repeatability is when a non-founder sales hire can close a deal from start to finish. This signals that the value proposition and process are teachable, which is the first true sign of a scalable go-to-market motion.