Eye On A.I. · 2026-06-12 · 57 min
Zendesk went private two weeks before ChatGPT launched, and the moment it came out, it was obvious that customer service would never be the same again. Shashi Upadhyay, head of product, engineering, and AI at Zendesk, joins Craig Smith to explain what the company has built since: a self-improving AI system that doesn't just resolve tickets but learns from every failure, studies what the human did to fix it, and gets measurably better over time. He calls it the resolution learning loop, and for Zendesk's best customers, it's already resolving 70 to 90% of incoming tickets autonomously, up from the 10 to 20% that chatbots managed just a few years ago. The conversation goes deep on the engineering decisions that actually matter: why hallucination is a feature, not a bug, and why the real challenge is knowing exactly when to switch from creative AI to deterministic code; why Zendesk acquired Forethought and what made their approach to going live in days rather than months so valuable; and why, despite all the momentum, Upadhyay estimates we are only about 5% through the adoption of AI in customer service.
How Modern Science Got Consciousness Wrong From the Start | Philip Goff59 / 100AI Is Reading 15 Million X-Rays a Year With No Human in the Loop | Prashant Warier, Qure.aiOnly 12% of Companies Generate Value From AI. Here's What They're Doing | Sanjeev Vohra, GenpactIndia Is Becoming an Architect of the Global AI Order | Ivana Bartoletti of WiproThe New BRAIN Of the Enterprise | Ryan Gavin