What if giving customers more value is exactly what's making them leave? Kellie Snyder, Chief Customer Officer at LinkSquares, joins Josh Schachter after a two-year replatform to fully agentic contract management. She unpacks how AI reshaped their customer 360, the retention mistake hiding in their onboarding, why digital-first went too far, and how to bring human engagement back without losing scale. A candid look at retention, migration, and rebuilding human engagement in the AI era.Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com---What You'll Learn- How LinkSquares went fully agentic in contract management- Building a real customer 360- Why "show them everything" was killing retention- Migrating legacy customers without scaring them off- AI enablement when teams sit at different skill levels- Right-sizing human engagement after over-rotating on digital-first- Tying value realization to pre-sales business outcomes---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Timestamps0:00 - Preview and Meet Kellie Snyder1:50 - What LinkSquares does, new agentic platform3:10 - Kelly's remit as the CCO at LinkSquares3:50 - Rob's story and the golf scholarship6:06 - AI transformation inside the post-sales team7:39 - Building the customer 3609:09 - How Kellie personally uses Claude10:45 - Sharing skills and wins across CSMs11:30 - Biggest speed bump going AI-native13:48 - The two-year replatform & impact on post-sales18:29 - Migration & killing one-size-fits-all onboarding20:27 - Investing in customer education22:33 - Quantifying value realization23:23 - What's taken longer than expected25:40 - Success one year out26:52 - A question for other CCOs---Where to Find the GuestKellie Snyder: https://www.linkedin.com/in/kellieasnyder/ ---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

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