The $50M Pricing Gamble and Intercom's AI Reinvention

What does it take to reinvent a billion-dollar SaaS company in the age of AI? For Intercom, the answer was refocusing the business, betting everything on an AI-first future, and a $50 million pricing model gamble. In this episode, co-founder Des Traynor pulls back the curtain on the bold moves that reset Intercom’s trajectory and turned its AI agent, Fin, into a powerhouse that resolves 65% of customer conversations. If you’re leading AI transformation, this is the playbook: how to make the painful cuts, how to reset culture, and how to price AI in a way that actually works. It’s not theory—it’s the story of one of the biggest AI reinventions in SaaS.