Pavilion AI in GTM live session: My AI Chief of Staff: How I Run GTM with Claude with Charlie Cowan
The second in our Pavilion AI in GTM live sessions.
Charlie Cowan, CEO of Kowalah, will show, live, how he's built an AI Chief of Staff that runs alongside him every day.
Not a slide deck about what's possible. An actual working setup where AI handles his pipeline reviews, preps his sales calls, drafts follow-ups, scans his meetings for commitments, and delivers a morning briefing before he's finished his coffee.
He'll walk through the specific workflows he's built using Claude's Cowork mode, including Brian (his AI sales ops manager who processes calls and manages deal state), John (his AI CRO who stress-tests deals and delivers daily pipeline briefings), and Rosalie (his AI EA who tracks commitments across email, Slack, and meetings). These are digital agents that replicate the work that would have been done by human colleagues.
Expect a live demo, Charlie's lessons on what works and what doesn't, and a Cowork plugin that will help you get started building your own AI-powered operating system.