Episode #221: John O’Donnell — Selling AI Trust When Your Best Outcome Is Invisible
How do you sell infrastructure that works best when nothing bad happens?
For GTM leaders, founders, and sellers building pipeline in category-creating, mission-critical sales motions.
John O’Donnell leads go-to-market at Alice, where he sells AI trust and safety to the top foundation model companies and the enterprises deploying AI in production. Before Alice, he built pipeline at Rapid7 in cybersecurity and led GTM in music distribution. In this episode, John breaks down his “method acting” approach to selling, why storytelling beats feature pitches in invisible-infrastructure categories, the milestone approach Alice uses to convert AI FOMO into committed deals, and why he sees the AI trust category today as the cybersecurity space in 2008-2010. He also shares the one discovery question most enterprise sellers never ask: “Can you live with your current situation for another year?”
WHAT YOU’LL HEAR
– The “method acting” framework for entering a buyer’s world before the first call
– Why Alice leans on storytelling and 200+ PhD dark web experts instead of feature pitches
– The milestone approach for converting AI FOMO buyers into committed deals
– What breaks when you scale founder-led sales too fast, and how to train a team to replicate it
