First Customers (GTM)

When do I know it's time to hire a salesperson instead of doing it myself?

A starting point

Not until the motion is repeatable and you can predict it. A useful bar: do at least ~50 demos and hit a win rate around 20% or higher before you hand it off, so you're transferring a working playbook, not chaos. Hire too early and you'll blame the rep for a process that was never figured out.

Go deeper

Read

📖 Book
Freemium Intermediate

Founding Sales: The Early Stage Go-to-Market Handbook

From foundingsales.com by Peter Kazanjy book (~400 pages)

Why we picked it

The authoritative handbook on founder-led sales, written for technical/first-time sellers building B2B SaaS. Readable free online via membership, and covers the whole motion end to end.

  • Do ~50 demos and hit a ~20%+ win rate before hiring your first sales rep.
  • Discovery before demo, understand the problem before you pitch.
  • Dedicated chapters on prospect outreach and demo appointment setting.
  • Turn founder selling into a documented, repeatable, transferable process.
Open foundingsales.com →
📄 Article
Free Intermediate

Founder-led sales

From First Round Review by First Round Review ~20 min read

Why we picked it

First Round has coached hundreds of founding teams through 0-to-$1M ARR; this is their tactical guide to selling in the earliest, hardest days. High signal, no fluff.

  • Founders must sell early, nobody sells the product better than you at first.
  • Build selling muscles with small exercises like a 'turbo rapport' challenge.
  • Self-diagnose whether your selling narrative is actually landing.
  • Craft buyer personas and pitch messaging before scaling.
Open review.firstround.com →

People also ask

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