Heading to Vegas this May? Join Josh at Pulse 2026 and come say hi—your oversized fluorescent daiquiri is on him. No catch.Grab your ticket at gainsightpulse.com and use code UNCHURNED for a special rate.Rob Edmondson, CCO at Ironclad - an AI contracting platform - brings a military-grade operating philosophy to customer outcomes: mission first, people always.In this episode, he breaks down what happened when his team used AI to predict churn — and why the results blew up their assumptions about what "good adoption" actually looks like.Rob reveals how down-market customers who adopted AI features too early actually churned more, why enterprise renewal patterns look nothing like daily usage. He also gets honest about the governance-vs-freedom tension every leader is navigating with AI tools right now.---Timestamps0:00 - Preview & introduction1:40 - Meet Rob Edmondson, CCO of Ironclad4:01 - Rob's career origin story5:03 - "Mission first, people always" - leadership from the military9:15 - How Rob enables a people-first culture across his teams11:05 - Using AI internally to predict churn & the surprising findings14:22 - Building a four-stage maturity model from churn prediction data16:35 - The AI vibe check: governance vs. freedom balancing act20:20 - Can you mandate AI usage? 21:57 - Tying every AI agent to an OKR22:40 - Ironclad's OKRs & Driving AI feature adoption---What You’ll Learn- How Ironclad built an AI model that predicts churn six months out- The difference between enterprise and SMB "digital signatures" of healthy customers- How to build a four-stage customer maturity model with measurable adoption gates- Why Rob ties CSM compensation to stage-progression KPIs, not activity metrics- What "mission first, people always" means when translated from the military to SaaS- How Ironclad balances AI governance with giving teams freedom to experiment- What an AI roadmap looks like when every agent is tied to an OKR---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find the GuestRob Edmondson: https://www.linkedin.com/in/redmondson/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

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