Video · ~35 min

Enterprise Sales for Founders

Pete Koomen · Y Combinator Startup School Free Beginner

Pete Koomen took Optimizely from zero to $100M+ ARR, and here he breaks the enterprise funnel down for exactly the person who finds it terrifying: the technical founder who has never sold. It is the clearest short primer we know on how a builder starts closing real deals.

  • Founders can and should run enterprise sales themselves early, treating each deal as a source of product feedback
  • Map the funnel stage by stage and know which stakeholder you need at each one
  • Identify a real champion inside the account and use them to reach the economic buyer
  • A repeatable, learnable process beats charisma when selling complex software
Open on ycombinator.com ↗

It answers 15 questions

  1. How do I land my first enterprise customer when nobody has heard of us?
  2. How do I run a sales call without sounding like a pushy salesperson?
  3. Cold email or cold LinkedIn/DM, what works better for reaching first customers?
  4. Who do I actually sell to inside a big company, and how do I find the decision-maker?
  5. When do I know it's time to hire a salesperson instead of doing it myself?
  6. What sales process should I follow if I've never sold anything before?
  7. Should I use design partners, and how do I structure the deal?
  8. As a technical or first-time founder, how do I actually run a good sales call?
  9. How do I follow up after a good sales call without being annoying or looking desperate?
  10. How do I sell to enterprises and large companies as a tiny unknown startup they have never heard of?
  11. How much of my week should I spend on sales versus building the product in the early days?
  12. How do I keep a clean sales pipeline and track deals when I am the only salesperson?

And 3 more across the hub.

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. 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
  4. A tactical follow-on covering the channels and motions top B2B startups scale after the first ten. Grounds distribution... Lenny's Newsletter Article · ~15 min read How to win your first 10 B2B customers Lenny Rachitsky
  5. 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
  6. 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
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