How to Sell AI Into the Enterprise: Pilots, Pricing, and Closing 12-Month Deals

What does it really take to sell an AI-native product into the Fortune 500? In this episode of Founded & Funded, Madrona Managing Director Matt McIlwain sits down with two founders deep in the trenches of enterprise AI adoption, Esha Joshi (Co-founder, Yoodli⁩) and Anup Chamrajnagar (Co-founder, Gradial.) Their companies are selling into some of the world's most complex organizations, like Google, SAP, Snowflake, Databricks, and more. And they break down what founders often underestimate about enterprise AI sales. They dive into: Why most AI pilots fail and how to prevent it The "three-legged stool" of enterprise sales How AI review boards are reshaping buying cycles Securing long-term contracts Pricing AI: seats vs. usage vs. outcomes Navigating non-deterministic AI failures with customers Building champions who accelerate their careers with AI If you're building an AI-native company and selling into enterprises, this is for you. Full Transcript: https://www.madrona.com/this-is-how-fortune-500-companies-are-buying-ai-today Chapters: (00:00) – Introduction (03:37) – Early AI Pilots: What Worked (and What Didn't) (05:01) – Sell Pain, Not Features (06:25) – Why Enterprise Expectations Are Higher Now (07:48) – Moving From "Wow" Factor to Durable Outcomes (09:17) – How to Structure a Pilot That Converts (10:35) – Expanding Beyond the Initial Wedge (13:41) – Turning Pilots Into 12-Month Contracts (14:47) – Navigating Procurement & AI Governance Boards (16:02) – What's Changed (and What Hasn't) in Enterprise Sales (16:45) – How to Increase Deal Velocity (19:39) – Using AI to Improve Your Own Sales Ops (20:20) – Are You Replacing Jobs with AI? (23:14) – Building Career-Accelerating Champions (23:46) – When AI Outputs Go Wrong (Real Stories) (25:23) – Why the Pilot Never Stops (29:04) – Pricing AI: Seats vs. Usage vs. Outcomes (34:48) – Go-To-Market Partnerships That Unlock Enterprise (37:25) – The Role of Forward-Deployed Engineers (38:44) – Final Advice for AI Founders Selling to Enterprise