{"version":1,"type":"rich","provider_name":"Libsyn","provider_url":"https:\/\/www.libsyn.com","height":90,"width":600,"title":"How to Sell AI Into the Enterprise: Pilots, Pricing, and Closing 12-Month Deals","description":"What does it really take to sell an AI-native product into the Fortune 500? In this episode of Founded &amp;amp; Funded, Madrona Managing Director Matt McIlwain sits down with two founders deep in the trenches of enterprise AI adoption, Esha Joshi (Co-founder, Yoodli\u2069) and Anup Chamrajnagar (Co-founder, Gradial.) Their companies are selling into some of the world\u2019s 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 \u201cthree-legged stool\u201d 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) \u2013 Introduction (03:37) \u2013 Early AI Pilots: What Worked (and What Didn\u2019t) (05:01) \u2013 Sell Pain, Not Features (06:25) \u2013 Why Enterprise Expectations Are Higher Now (07:48) \u2013 Moving From \u201cWow\u201d Factor to Durable Outcomes (09:17) \u2013 How to Structure a Pilot That Converts (10:35) \u2013 Expanding Beyond the Initial Wedge (13:41) \u2013 Turning Pilots Into 12-Month Contracts (14:47) \u2013 Navigating Procurement &amp;amp; AI Governance Boards (16:02) \u2013 What\u2019s Changed (and What Hasn\u2019t) in Enterprise Sales (16:45) \u2013 How to Increase Deal Velocity (19:39) \u2013 Using AI to Improve Your Own Sales Ops (20:20) \u2013 Are You Replacing Jobs with AI? (23:14) \u2013 Building Career-Accelerating Champions (23:46) \u2013 When AI Outputs Go Wrong (Real Stories) (25:23) \u2013 Why the Pilot Never Stops (29:04) \u2013 Pricing AI: Seats vs. Usage vs. Outcomes (34:48) \u2013 Go-To-Market Partnerships That Unlock Enterprise (37:25) \u2013 The Role of Forward-Deployed Engineers (38:44) \u2013 Final Advice for AI Founders Selling to Enterprise ","author_name":"Founded &amp; Funded","author_url":"https:\/\/www.madrona.com\/","html":"<iframe title=\"Libsyn Player\" style=\"border: none\" src=\"\/\/html5-player.libsyn.com\/embed\/episode\/id\/40306285\/height\/90\/theme\/custom\/thumbnail\/yes\/direction\/forward\/render-playlist\/no\/custom-color\/88AA3C\/\" height=\"90\" width=\"600\" scrolling=\"no\"  allowfullscreen webkitallowfullscreen mozallowfullscreen oallowfullscreen msallowfullscreen><\/iframe>","thumbnail_url":"https:\/\/assets.libsyn.com\/secure\/item\/40306285"}