The AI Diaries: Don't Get Trapped — Always Include an Exit Clause | with Jeremy Hyde

If you're signing a multi-year AI contract right now, today's guest thinks you might be out of your mind — and he can back it up. Jeremy Hyde is the Senior Director of Customer Service at Sun Country Airlines, where he leads a lean, high-tenure team of ~125. He's implemented AI tools across the contact center, gotten burned by a zero-ROI auto summary rollout, negotiated exit clauses into every vendor contract, and watched one vendor refuse to budge — which tells him everything he needs to know about that partnership. In this episode: AI contracts, change management failures, agent assist that tenured agents ignored, a knowledge base chatbot pilot that's surprising everyone, and why the legal landscape around AI is the Wild West — and vendors aren't warning you about it. 🎙️ Guest: Jeremy Hyde — Senior Director of Customer Service, Sun Country Airlines ─ 📌 CHAPTERS 00:00 Intro — Jeremy Hyde & Sun Country Airlines 01:21 The pattern every wave of tech repeats — and AI is no different 05:03 Auto summary: zero ROI, zero ACW change, and what went wrong 08:30 The change management fix: "This is a gift. Stop editing the notes." 09:08 Exit clauses on every AI contract — why Jeremy asks and what happened when a vendor said no 13:51 Low commitment, high flexibility: why Jeremy won't sign a multi-year AI deal 17:18 Sometimes vendor #1 is tuition for vendor #2 18:59 Agent assist that tenured agents ignored — and the pivot to a knowledge base chatbot 21:31 Push vs. pull: not every AI assist should be proactive 23:29 Pilot surprises: what agents actually love vs. what Jeremy expected 27:36 Warning label you'll never see in a pitch deck: AI's legal Wild West 29:53 What Jeremy's building — Midwest Contact Center Association & Work From Home Alliance ─ 🔗 LINKS Connect with Jeremy Hyde on LinkedIn:   / jeremyhyde   Connect with Kate:   / bettercallkate   ─ 📍 Subscribe to Business Kate for more AI Diaries — unfiltered conversations with CX and contact center leaders navigating AI in the real world.