Article · 15 min read

Who To Hire As The First Salesperson In Your Startup

Dave Kellogg · Kellblog Free Intermediate

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.

  • 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
Open on kellblog.com ↗

The question it answers

  1. Should I hire a salesperson yet, or keep selling founder-led until I hit a certain revenue?

Read with it

  1. This is the practical companion to the 'who' question: it says hire only once founder-led sales works well enough that someone... Sierra Ventures (Ascend) Article · 12 min read How to Hire a Startup's First Sales Hire: Skills, Pitfalls, and a Plan Sierra Ventures
  2. The global playbooks assume a US-style buying process; this one is written for the Indian enterprise reality, where the sale... Blume Ventures Article · 25 min read The Rough Guide to Building an Enterprise SaaS Dhandha in India Blume Ventures (with Aakrit Vaish, Haptik)
eChai Partner Brands The partnership →