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Podcast
[Un]Churned – The No. 1 Podcast for Customer Retention
Hosted by Gainsight · EN
If you're experimenting with automation, questioning the traditional post-sales model, or trying to drive more value with less headcount, you're in the right place. AI won’t fix churn, but these conversations might.
Retention is the new growth, AI is rewriting the rules. Hosted by Josh Schachter, SVP of Atlas at Gainsight, [Un]Churned—the No. 1 podcast for retention and Customer Success leaders—features real talk with the sharpest minds in the Customer Success space. We dig into how teams are scaling smarter, activating AI agents, and redesigning the customer journey for lasting impact.
45episodes
Episodes
Newest firstAll episodes
Claude Code Cut Dev Cycles 60% Then Forced an Org Redesign ft. Margo Martin & Jason Goldsmith (Deltek)
2d ago00:36:32Tap to summarizeWant the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.Deltek's CCO Margo Martin and newly-appointed VP Customer Strategy & Services at Deltek Jason Goldsmith reveal how Claude turned three siloed post-sale teams into one AI-first machine and why they built a brand new executive role just to keep up.Deltek didn't just adopt AI. They restructured around it. After Claude and Claude Code cut documentation timelines by 80% and dev cycles by 50-60%, CCO Margo Martin realized her three post-sale orgs (implementation, CS, and support) were quietly duplicating AI work. Her fix? A brand-new "AI convergence" role . And she picked an internal boomerang employee to run it.In this episode, you'll hear exactly how they built the business case, picked the right leader, and what's next on the roadmap.---What You'll Learn- The tradeoff between touchless implementation and long-term customer stickiness- How Claude Code cut custom implementation timelines by 50-60%- Why Deltek reduced customer documentation & training time by 80%- How to spot "AI silos" forming across your org before they cost you- What it takes to build (and pitch) a brand-new AI strategy role internally- Deltek's build-vs-buy framework for AI tools- How CX leaders are using personal AI "chiefs of staff" day-to-day- Why Deltek is rebuilding its entire customer journey around AI- How to balance automation speed with customer stickiness ---Timestamps0:00 - Preview & Intro1:50 - Meet Margo Martin & Jason Goldsmith (Deltek)2:45 - What Deltek does & org structure6:40 - How Claude Code changed everything 10:23 - Duplicate AI efforts & the new VP of AI strategy role14:45 - Why Jason was the pick19:10 - Jason's 30/60/90 day plan24:10 - Predicting the first team to join Jason's org26:45 - Personal AI chiefs of staff28:28 - Build vs. buy: Deltek's AI tooling philosophy32:56 - KPIs and metrics for AI transformation---Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com---Where to Find the GuestMargo Martin: https://www.linkedin.com/in/margomartin-/Jason Goldsmith: https://www.linkedin.com/in/jwgoldsmith/---Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/
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The Old Playbook Is Obsolete. The New One Isn't Built. ft. Amanda Moran (Darktrace)
4d ago00:22:40Tap to summarizeSix months in, Amanda Moran, is rebuilding customer success from scratch.She spent eight years at LinkedIn mastering the old playbook: rules, workflows, perfectly timed emails. Now she's VP of Digital Customer Success at Darktrace, a cybersecurity company betting its future on securing AI itself.But she's stuck on the question keeping every CS leader up at night. Autonomous agents aren't here. You can feel them coming. So what do you build right now, without wasting months on work the agents will replace?Josh Schachter pushes into the hard parts: the data nobody connects, and why the next cybersecurity battle is the AI you're about to deploy.This one's for anyone building toward a future that hasn't arrived.---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---What you'll learn- Why rules-based outreach is on its way out, and what comes next- How to build CS today without locking in throwaway automation- The pooled support model behind 5 people serving 10,000 customers- Why agentic AI is cybersecurity's next frontier- The hidden signals in community and learning data- What CS leaders are all quietly trying to figure out--- Timestamps0:00 - Preview & Introduction1:42 - Meet Amanda Moran & Overview of Darktrace3:00 - Transitioning from LinkedIn to cybersecurity4:03 - Building AI-driven email engagement6:50 - The Digital CS org at Darktrace 9:20 - The pooled model11:39 - Renewals at Darktrace12:45 - Securing AI itself: the July launch14:17 - Internal AI enablement15:17 - Building CS before the agents take over17:50 - The data problem20:10 - The in-between phase nobody has cracked---Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com---Where to Find the GuestAmanda Moran: https://www.linkedin.com/in/amandammoran/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/
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He Created a Job Title 1,000+ People Now Have ft. Yash Tekriwal (Clay)
1w ago00:45:44Tap to summarizeMost companies think of education as a support function, the real shift is treating it as a go-to-market engine.In this episode of the UnChurned Podcast, Josh Schachter and Samantha Murray sit down with Yash Tekriwal, Head of Go-to-Market Engineering Ecosystem at Clay, to unpack how he became the company's first-ever GTM Engineer, why Clay rebranded its entire education team, and what it actually takes to build a learning ecosystem people don't just consume, but live inside of.Yash shares the origin story of the GTM Engineer role, why he believes "education" has become a dirty word in tech, and how Clay is rethinking everything from LMS platforms to certification to attribution.They also dive into:- The origin story behind the first-ever "GTM Engineer" title- Why Clay killed its education team and rebranded to a GTM engineering ecosystem- Why traditional LMS platforms get learning fundamentally wrong- The "control the environment, not the process" philosophy of learning- Why brand affinity and "vibes" matter more than marketing attribution- Rethinking certification and skill assessment in the age of AIIf you're building a GTM team, leading customer education, or trying to figure out how learning and community actually drive growth, this episode is a masterclass in building an ecosystem instead of a content library.Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.Chapters00:00 – Intro & Backstory01:03 – Yash's Pre-Clay Career and Failed Startups05:30 – Why He's More Of A Founder Than When He Was One06:32 – Becoming Clay's First-Ever GTM Engineer09:41 – Category Creation and Market Sizing13:42 – "We Killed The Education Team At Clay"15:36 – Why Education Became A Dirty Word In Tech21:08 – Yash's Path From Teacher To GTM Engineer24:54 – The Build vs. Buy Problem With LMS Platforms28:09 – Control The Environment, Not The Process32:37 – Why Attribution Doesn't Matter — It's All Vibes36:18 – Inside Clay's Six-Pod GTM Ecosystem42:16 – Yash's One-Year Goal: Rebuilding CertificationJosh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.comWhere to Find the Guest:Yash's LinkedIn: https://www.linkedin.com/in/yashtekriwalWhere to Find the Hosts:Josh's LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/Samantha's LinkedIn: https://www.linkedin.com/in/samantha-murray613/
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Your North Star Metric Is Wrong (and It's Killing Your Retention) ft. Mark Roberge (Stage 2 Capital)
2w ago00:39:40Tap to summarizeMost founders treat product-market fit like a feeling. Mark Roberge thinks that's as absurd as calling profit a feeling.The founding CRO of HubSpot, Harvard Business School lecturer, and Stage 2 Capital co-founder joins Josh to break down his new book, The Science of Scaling. The argument at the center of it - the decision of when and how fast to scale shouldn't be a gut call. It should be gated on retention.Mark shares the leading indicator of retention (the one metric that predicts churn in a customer's first month), the 5-50-500 playbook a Microsoft leader used to launch new products, why Drift's founder flew across the country to onboard $50/month customers, and what "AI-native sales team" should actually mean in 2026 (with numbers attached).If you work in Customer Success, this episode makes the case that you own the most strategic metric in the company. All proceeds from Mark's book go to McLean Hospital for mental health care.---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---What You'll Learn- Why we scale haphazardly, not scientifically- A quantitative definition of product-market fit - How to design a leading indicator of retention- Real LIR examples from Slack, Harvey, Facebook, and Gainsight - The three maturity levels of an LIR- How a Microsoft leader used the 5-50-500 rep model to de-risk new product launches- How to pick your threshold based on the blitzscale risk in your category- Why product-market fit and go-to-market fit must be sequenced, not pursued at once- How to know when to move past founder-led sales - How to bring unit economics into board meetings - Why blitzscaling fails more companies than it saves (and why VCs push it anyway)- The two metrics that define an AI-native sales team in 2026- Mark's four phases of the AI revolution in go-to-market ---Timestamps0:00 - Preview & Intro1:30 - Meet Mark Roberge3:07 - The Science of Scaling (All book proceeds go to McLean Hospital)7:30 - We scale haphazardly, not scientifically9:06 - Microsoft's 5-50-500 playbook13:19 - Is product-market fit a feeling?15:48 - The leading indicator of retention, explained17:30 - Time to value vs. recurring value19:42 - Designing your own LIR24:04 - Why go-to-market fit comes after PMF26:06 - Pitching this framework to VCs28:15 - How to know when you have go-to-market fit31:15 - Bringing the science to larger companies33:00 - When to move beyond founder-led sales35:51 - AI and the four phases of the GTM revolution37:20 - What "AI-native sales team" means in 2026---Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com---Where to Find the GuestMark Roberge: https://www.linkedin.com/in/markroberge/The Science of Scaling: https://a.co/d/0boDpDUcStage 2 Capital: https://www.stage2.capital/---Where to Find the Host: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/
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How to Sell Community to a CEO Who Doesn't Care About Community ft. Chris Catania (Esri)
2w ago00:39:12Tap to summarizeMost leaders treat community as a marketing channel. They're leaving the real advantage on the table.Chris Catania , Head of Community at Esri built community from a love of live music. Lately, he wrote the playbook. In this episode he joins Erica Kuhl, who scaled Salesforce's legendary Trailblazer community, and Josh Schachter to make the case that community isn't a nice-to-have. It's a strategic operating system competitors can't copy.From Lego's near-bankruptcy turnaround to Marc Benioff, CEO of Salesforce, demanding harsher feedback, this episode reframes what community can do for a business.---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---What You'll Learn- Why community is a service to every team, not a marketing channel- The importance of speaking each executive's language- The "fake flowers vs real flowers" test for authentic community- Why community-driven companies build an advantage rivals can't catch- The three E's: enablement, experience, evaluation- How to set a North Star while delivering ROI in small wins---Timestamps0:00 - Preview & Intro1:56 - Meet Chris Catania6:27 - Three founders, one music origin story10:17 - The Lego turnaround that saved the brand14:25 - Fake flowers vs real flowers17:28 - Why nobody likes the word "community"22:05 - The Marc Benioff feedback story (CEO of Salesforce)24:24 - Is Voice of the customer underleveraged?31:47 - Erica ran Salesforce's first Twitter handle33:22 - Community as a service and the unfair advantage37:20 — One takeaway: the three E's---Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com---Where to Find the GuestChris Catania: https://www.linkedin.com/in/christophercatania/Website: https://chriscatania.co/---Where to Find the Hosts: Erica's LinkedIn: https://www.linkedin.com/in/ericakuhlJosh's LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/
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Ex-Microsoft AI Lead: Why Smart Teams With Big Budgets Still Fail at AI ft. Brian Evergreen (The Future Solving Company)
3w ago00:23:10Tap to summarizeEveryone's racing to "do AI." Almost nobody can say what for.Brian Evergreen, Forbes AI thought leader, author of Autonomous Transformation, ex-Microsoft, Founder & CEO of The Future Solving Company joins Josh Schachter to flip the playbook.Start with a problem? That traps you in incrementalism. Be data-driven? There's no data about the future. The old industrial-era moves quietly sabotage every AI rollout.Brian's fix: solve for a future you can feel. Then reverse-engineer it with one question: what would have to be true?Inside: the reason-tree framework, the JFK moon test, and how to make renewal a panic-level no-brainer your champion fights for. You don't need the CEO's permission to start.---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---What you'll learn- Why "start with a problem" caps your upside- How "data-driven" quietly became unscientific- Why green scorecards hide a shrinking business- The JFK test for a visceral vision- The reason-tree mapping "what would have to be true"- Whether a revenue number can be a vision- Helping customers build their own vision- Starting all this without executive buy-in--- Timestamps0:00 - Preview & Introduction2:00 - Meet Brian Evergreen (Ex-Microsoft)4:30 - Why the digital-era playbook fails for AI5:25 - "Start with a problem" is an incrementalism trap6:00 - How "data-driven" turned unscientific7:19 - All green scorecards but shrinking market share8:40 - Netflix solved the same future twice9:35 - No value vision? Don't invest in AI yet12:40 - Getting over organizational inertia15:30 - The reason-tree: "what would have to be true?"18:25 - Can a vision be a number? (Replit's $1B ARR vision)19:50 - Why most "strategy" is just a SWOT board21:15 - You don't need the CEO's permission---Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com---Where to Find the GuestBrian Evergreen: https://www.linkedin.com/in/brianevergreen/Brian's Substack: https://newsletter.brianevergreen.com/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/
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The 45% Problem: Why Unit4 Cut Mid-Touch and Bet on AI ft. Jean de Villiers
3w ago00:33:24Tap to summarizeNo one celebrates a new ERP. No champagne. Just groans.Jean de Villiers, Chief Customer Officer at Unit4, wants to flip that script.Jean shares they have kept customers for 20+ years in an industry built on dread. Secret? He runs customer success like a business, not a cost center. He cut the safe middle option. He's betting big on AI agents. And he trains his whole team to have the uncomfortable conversations most people avoid.In this episode of Unchurned, Jean sits down with host Josh Schachter to unpack the playbook: why 45% of what customers pay for goes unused, how high-touch service drives a 50-point gap in customer promotion, and what it really takes to make people love the software they're supposed to hate.Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com---What You'll Learn- Why Unit4 runs CS as a profit center, not a cost- How to hit 30% contribution margin to EBITDA in post-sales- Why Unit4 cut mid-touch and kept only high and digital- Packaging every service into a self-serve catalog- Building an agentic digital CSM that feels high-touch- The 50-point NPS gap between high-touch and self-serve- Why 45% consumption is ERP's dirty secret- Training non-sellers on the Challenger Sale method- How AI plus human domain expertise wins together---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Timestamps0:00 - Preview and Introduction1:44 - Meet Jean de Villiers 2:45 - What Unit4 does and its four verticals4:32 - Customers who stay 20+ years6:32 - The org structure of post-sales7:32 - Running CS as a profit center under PE8:50 - Why they cut mid-touch9:45 - Packaging services into a catalog12:20 - The agentic digital CSM vision13:53 - Success For You: the high-touch subscription18:12 - Sunsetting on-premise product, migrating to cloud & Ava21:50 - The 45% consumption problem23:57 - The 50-point NPS difference25:30 - Challenger Sale training for everyone31:40 - Wrap-up---Where to Find the GuestJean de Villiers (Unit4): https://www.linkedin.com/in/jeandevilliers/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/
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How AWS's Developer Community Grew 3,600 Builders Across 110 Countries ft. Jason Dunn
4w ago00:26:10Tap to summarizeTwo hands. A free Slack channel. A spreadsheet. That was the entire toolkit when AWS asked Jason Dunn to build a developer community. Jason Dunn spent five years on building something people actually want to belong to. He grew a developer community into thousands of members spread across more than a hundred countries, working with far less budget and tooling than you'd expect.This conversation digs into what separates a living community from a glorified contact list. Why your earliest members carry so much weight. When to keep the door open and when to guard it. How to prove value when your best wins resist a dashboard. Why technical people walk the second something smells like a pitch. And how one small, slightly absurd reward became a badge people chased for months. A Real talk on getting people to show up for each other.Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com---What You'll Learn- Why the first members you pick set the tone forever- The day-zero choice: community for everyone or for someone- How to measure community when it's basically a vibe- The trick to getting members to report their own wins- Gamification with a lowercase G (and why it works)- The golden jacket story and pent-up demand- Why developers reject sales and marketing pipelines- Scrappy tools beat fancy platforms every time- The AI warning every new community manager needs---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 Jason Dunn2:22 - What community meant at AWS in 20193:45 - The day-zero decision every builder faces5:05 - From 200 invited seeds to 3,600 members6:39 - Keeping the gates too open, too early9:12 - Defining high-value member activity11:23 - Measuring & reporting up: output, reach, and Dev.to14:53 - The Content Reporting Tool (CRT)16:02 - The real motivation behind self-reporting18:24 - The Golden Jacket origin story & 130 jackets in one quarter21:28 - The AWS Community toolkit23:42 - Advice for new community managers51:00 — Don't fall in love with the tools53:00 — Humanity connecting with humanity---Where to Find the GuestJason Dunn: https://www.linkedin.com/in/jasonrobertdunn/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/
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The Retention Killer Hiding in Your Product Demos ft. Kellie Snyder (LinkSquares)
4w ago00:29:07Tap to summarizeWhat 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 - Kellie'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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The GTM Playbook Behind 133 Million Learners ft. Monika Saha (Articulate)
Jun 1600:35:06Tap to summarize133 million learners. 100% of the Fortune 100. And the woman steering go-to-market behind those numbers will tell you to stop chasing churn. Monika Saha, CCO of Articulate, doesn't trade in best-practice platitudes. In this episode she takes the sacred cows out back: why "customer education is a cost center" is half-wrong instead of all-wrong, when fighting retention is a flat waste of energy, and why PLG companies are quietly light-years ahead while everyone else optimizes the wrong thing. Host Josh Schachter pokes the bear. Co-host Samantha Murray pushes back. Monika doesn't blink. If you run customer success, education, or GTM and you're tired of being told what you already know, this one's built to make you uncomfortable in the good way.Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com---What You'll Learn- Why "customer education is a cost center" is partly true- How to standardize and modularize content so you stop reinventing the wheel- When improving churn is actually a waste of energy- How to segment a long tail so you invest where returns are real- Why PLG companies dominate in-app and digital motion- A simple QBR exercise to find AI-ready process bottlenecks- How to structure a number across a core product plus early cross-sells---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 Mac, Monika's dog1:08 - Meet Sam Murray, Gainsight & Monika Saha, Articulate2:11 - Articulate's Overview4:20 - Monika's remit as Chief Commercial Officer: trial to renewal5:37 - Lessons from her Gainsight CMO days9:00 - Customer education & internal enablement14:53 - Debate: is customer education a cost center?20:30 - Controversial take: when fixing churn is pointless23:43 - Why digital motion is foundational at a PLG company26:56 - Can non-PLG B2B companies experiment like this?28:48 - Embracing efficiency with AI32:30 - Hitting the number: core product vs cross-sell---Where to Find the GuestSamantha Murray: https://www.linkedin.com/in/samantha-murray613/Monika Saha: https://www.linkedin.com/in/monikasaha/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/
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