Article · 25 min read

The Sales Playbook for Founders

Tom Blomfield · Y Combinator Startup Library Free Intermediate

Blomfield (founder of Monzo and GoCarchless, now a YC partner) gives the concrete mechanics of closing that first B2B deal: pick one wedge product and sell it hard for a couple of weeks, run paid pilots not vague free design partnerships, and use opt-out contracts to convert. It is the tactical how-to for turning your one target customer into a signed, paying pilot while you are still employed.

  • Charge for the pilot: a paid pilot with clear success criteria is real proof; a long, undefined free design partnership is the most common founder mistake and proves nothing
  • Pick a narrow wedge and sell it aggressively for two weeks; if it does not land, switch the wedge rather than piling on features
  • Find and cultivate an internal champion who sells for you when you are not in the room, which is how a single evening-and-weekend deal actually closes inside a company

It answers 9 questions

  1. When do I know it's time to hire a salesperson instead of doing it myself?
  2. What sales process should I follow if I've never sold anything before?
  3. How is founder-led sales different for Indian founders selling to global (US) buyers?
  4. How do I follow up after a good sales call without being annoying or looking desperate?
  5. How do I sell to enterprises and large companies as a tiny unknown startup they have never heard of?
  6. How much of my week should I spend on sales versus building the product in the early days?
  7. How do I keep a clean sales pipeline and track deals when I am the only salesperson?
  8. How do I get my first paying customer BEFORE I quit, so I have real proof and not just belief?
  9. How do I sell confidently when I am the founder and also the youngest or least experienced person in the room?

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