When making your first sales hires, never hire just one person. Hire two. This instantly creates healthy competition and camaraderie. More importantly, it provides a crucial benchmark. If one succeeds and the other fails, you know the problem is the rep. If both fail, the problem is likely your product or market.
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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.
Small companies often overload their first salesperson with both new logo acquisition and existing account management. This is a trap. Prospecting will always lose out to servicing known customers. Plan for account continuity early to protect your growth engine, even before you can afford a second hire.
The founder, as the best salesperson, should always have a trainee shadowing them. This "double dips" on their time, turning every sales activity into a real-time training session. It's the most efficient way to transfer skills, duplicate the founder's success across a team, and build a scalable sales process based on modeling.
