Post by Kaylyn Knoll

Last week we brought ClickUp, The Table to Chicago. Tre Dita. Family-style Italian. Creekstone filet, handmade gramigna, and a tiramisu that had no business being THAT good. 14 leaders from financial services, higher ed, consulting, and market intelligence. Somewhere between courses, the real conversation started: how they're actually navigating AI inside their orgs. What came up: → Pilot fatigue. Everyone's experimenting. Almost no one's shipping to production. → The "one more tool" trap. AI layered on workflows that were already broken. → A demand for connected systems, not another point solution. To everyone who joined - you made this one special. Genuinely one of my favorite nights in this series so far. Thank you Frankie Vignone and Liam Mahoney for co-hosting with me and making this one a massive hit!