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Kellogg (ex-CEO Host Analytics, ex-CMO Salesforce, board-level SaaS operator) makes exactly the argument in our answer, and makes it sharper: hire someone who has already sold to your specific buyer (CFO vs CRO) at your current deal size with room to grow, not a big-logo rep who sold ten times higher. He names the trap directly, the early-career 'sales athlete' and the enterprise veteran who only knows nine-figure deals, and prescribes a 6 to 12 month founder-plus-seller 'three-legged race' so the rep inherits a process you proved together, not one you never wrote down.
Who To Hire As The First Salesperson In Your Startup
From Kellblog by Dave Kellogg 15 min read
- Match the hire to your buyer persona and current deal size, not to an impressive logo from a company selling far larger contracts
- Avoid both the green 'sales athlete' who needs a built-out playbook and the big-company veteran who cannot operate without a team feeding them pipeline
- Run 6 to 12 months as a founder-plus-seller pair so the rep learns the motion before you scale a team behind them
