Josh Schachter — SVP @ Gainsight | Host of [Un]Churned 🎙️ | Writing a book about the human side of building a startup 📕

About Josh

Hey, I'm Josh. I've spent my career at the intersection of product, AI, and customer retention. From founding startups to building new ventures inside organizations like BCG, the NFL, and Intuit, the through line has always been the same: how do you keep customers, and how do you scale that without breaking what makes it work? In 2020, I founded UpdateAI to help Customer Success teams get more value out of customer conversations using AI. That bet on the CS space paid off in ways I didn't expect. UpdateAI was acquired by Gainsight, and I joined as SVP of Strategy and GTM Development. Today I focus on one question: how do CS teams use AI to scale their impact without losing the human relationships that actually drive retention? My honest take is that most teams are either ignoring AI or overinvesting in automation that erodes trust. The teams getting it right are doing something more deliberate. 🎙️ I explore that through [Un]Churned, my podcast with some of the sharpest CS operators in the world, and through deeper writing at unchurned.substack.com. 📕 I'm also writing a book on how the world's most exceptional founders build thriving businesses by investing in human relationships, because the more I study what separates great companies from good ones, the more it comes back to that. If you lead Customer Success, Revenue, or a B2B SaaS org and want a grounded perspective on where this is all going, follow along.