Video · ~30 min

Enterprise Sales | Startup School

Pete Koomen · Y Combinator Free Intermediate

If your market is a small number of high-value customers, you are running an enterprise sales motion whether you call it that or not, and this is a practical, honest walkthrough of it. Pete Koomen (who took Optimizely to $100M ARR) breaks the funnel into prospecting, outreach, qualification, pricing, closing, and implementation, and makes the case that founders should do their own selling first. A good starting point for operating a low-count, high-value market rather than a generic sales pep talk.

  • When each deal is large, founders should run their own early sales to learn the customer's problem deeply before hiring a team.
  • The enterprise funnel has distinct stages (prospecting through implementation), and each one needs different attention when you only need a handful of wins.
  • Closing ten large customers is a very different game from acquiring a thousand small ones, and the relationship work continues long after the first signature.

It answers 2 questions

  1. How is founder-led sales different for Indian founders selling to global (US) buyers?
  2. How do I sell to enterprises and large companies as a tiny unknown startup they have never heard of?

Read with it

  1. The authoritative handbook on founder-led sales, written for technical/first-time sellers building B2B SaaS. Readable free... foundingsales.com Book · book (~400 pages) Founding Sales: The Early Stage Go-to-Market Handbook Peter Kazanjy
  2. Jen Abel has coached over 300 early-stage founders through their first sales, so this is grounded in what actually happens when... Lenny's Podcast Podcast · About 1 hour 16 minutes The ultimate guide to founder-led sales | Jen Abel (JJELLYFISH) Lenny Rachitsky with Jen Abel
  3. Blomfield (founder of Monzo and GoCarchless, now a YC partner) gives the concrete mechanics of closing that first B2B deal:... Y Combinator Startup Library Article · 25 min read The Sales Playbook for Founders Tom Blomfield
  4. An Indian founder story where the early demand test was manual, cold emails and direct outreach to find the first customers... Prime Venture Partners Podcast Podcast · ~50 min How Khadim Batti Built Whatfix Into a Global SaaS Leader Prime Venture Partners
  5. When your first ten will come from cold outreach, this guide gives you the full mechanics: building a target list, qualifying,... Close Article · Multi-chapter guide The Ultimate Startup Guide to Outbound Sales Steli Efti
  6. The single best thing ever written on customer conversations. It teaches you to ask about the customer's life and past... momtestbook.com Book · ~130 pages The Mom Test Rob Fitzpatrick
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