Essay

So you want to sell to the enterprise?

Benn Stancil · Benn Stancil (Substack) Free Intermediate

Benn Stancil cofounded a company that sold into large enterprises, and this essay is an unusually honest account of how slow, bureaucratic, and personality-driven that process really is, procurement, security review, and legal redlines included. It is the piece to read when you need a reality check on timelines before you commit months of runway to one enterprise logo. Share it with a cofounder who thinks enterprise sales will move quickly once you land one meeting.

  • Why enterprise deal timelines almost always run longer than founders initially plan for
  • The hidden stages, security review, legal, procurement, that stall deals after the buyer already says yes
  • How to decide up front whether a specific enterprise deal is worth the months it will take
Open on benn.substack.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?

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