Essay

Enterprise sales for hackers

Y Combinator Startup Library Free Beginner

Written for the founder who built the product and is now terrified of the word sales, this argues the skill set is closer to debugging than performing: listen carefully, form a hypothesis about the buyer's problem, test it, iterate. It is a good mindset reset if you keep avoiding outbound because you assume you are bad at it. Read it before your next customer call, not after you have already talked yourself out of making one.

  • Selling and building share the same underlying skill: diagnosing a problem precisely
  • Why technical founders often make excellent early salespeople once they reframe it that way
  • A simple way to treat each sales call as a hypothesis you are testing
Open on ycombinator.com ↗

The question it answers

  1. How do I sell to enterprises and large companies as a tiny unknown startup they have never heard of?

Read with it

  1. The author of Crossing the Chasm explaining beachhead selection in plain, modern language, the fastest way to absorb the... Lenny's Podcast / Lenny's Newsletter Podcast · ~75 min Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market Lenny Rachitsky & Geoffrey Moore
  2. The best book on positioning against competitors by understanding the alternatives customers actually consider. Directly turns... aprildunford.com Book · ~200 pages Obviously Awesome: How to Nail Product Positioning so Customers Get It, Buy It, Love It April Dunford
  3. A data-backed teardown of how companies like Figma, Gusto, and Vanta actually sourced their earliest customers. Replaces... Lenny's Newsletter Article · ~15 min read How today's fastest-growing B2B startups found their first ten customers Lenny Rachitsky
  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. 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
  6. Steli Efti (YC alum, co-founder of Close CRM) is one of the most trusted voices on startup outbound and cold email, practical,... Close Article · article series The Close Sales Blog (Steli Efti on cold email & founder sales) Steli Efti
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