Why Messy Data Is Not the AI Blocker You Think It Is with Glean Head of Product Emrecan Dogan

In this episode of Shift AI, Emrecan Dogan, Head of Product of Glean, joins host Boaz Ashkenazy for a wide-ranging conversation on what it actually takes to give enterprise AI real organizational context.Emrecan has convinced countless CIOs and CEOs to stop chasing a data cleanup project that he says will never finish. Instead he makes the case for leaving the mess exactly where it is and solving the problem somewhere else entirely, a position that runs against nearly everything companies think they need to do before they can "get onto AI." He also lays out a theory of why knowledge workers spend half their AI time just re-teaching context, and what it would take to get that number to zero.This one is for CIOs, chief AI officers, heads of product, and platform and data leaders who are being told to fix their data before they can move on AI, and who want a second opinion.Chapters[00:00] Welcome and introduction[00:33] Emrecan's path to Glean: entrepreneur, LinkedIn, Stripe, and a warning from a VC[02:36] First paid job: fixing bikes in Turkey[04:19] What Glean actually does: the work AI platform explained[06:53] The onboarding moment of truth and losing Glean when you leave[09:40] Why organizational data, not model choice, is the real moat[10:47] Seven years of infrastructure work before the GPT moment[13:00] The pipe dream of cleaning up your data stack first[15:36] "Bot sitting": the hidden cost of teaching context to AI every day[17:59] Why picking a single model provider is one of the worst bets you can make[23:37] Token yield, marginal cost intelligence, and the "half my budget is wasted" problem[30:36] Assistants versus agents: a framework for when each one applies[36:31] What's coming next: durable, multiplayer artifacts and proactive AI[40:34] Closing question: the future of work in two wordsConnect with Emrecan DoganLinkedIn: https://www.linkedin.com/in/emrecandogan/Glean blog: glean.comConnect with Boaz AshkenazyLinkedIn: https://www.linkedin.com/in/boazashkenazy/Email: [email protected]