Unchurned

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.He built the dashboards. Now he's questioning if they'll even exist in two years.Ziv Peled just added "Chief AI Officer" on top of Chief Customer Officer to his title at AppsFlyer. In this episode, he breaks down what that actually means: not a figurehead role, but hands-on rebuilding of workflows, architecture decisions, and the mindset of an entire org. Josh and Ziv chat about how AppsFlyer built their own $20/month AI pipeline on top of Gong instead of replacing it, why "build vs. buy" isn't the binary everyone thinks, what happens to your AI costs, and why "50x ROI" claims are mostly noise; plus the line that stopped the whole conversation: "When is the last dashboard?"---What You'll Learn- What a Chief AI Officer actually does day-to-day - Why AppsFlyer upsold into Gong instead of churning- Why most AI ROI metrics ("10x, 50x") don't hold up- What's changing with AI vendor pricing/consumption limits- How to think about AI security risk without a rulebook to follow yet---Timestamps0:00 - Preview & Intro1:30 - Meet Ziv Peled, CAIO at AppsFlyer 4:40 - How the CAIO role came to be6:50 - Build vs. buy: Salesforce, Gong, and AppsFlyer's own MCP9:25 - Why AppsFlyer isn't churning off Gong (they upsold)12:20 - What is Mythos? (and the quantum computing tangent)13:50 - The 90-minute video, 2-minute AI analysis story14:42 - How AI is changing competitive advantage16:10 - What it actually takes to become an AI-native company19:33 - Rapid fire: adoption, measurement, expense, security---Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com---Where to Find the GuestZiv Peled: https://www.linkedin.com/in/zivpeled---Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

Want 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/

Six 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/

Most 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/

Most 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/

Most 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/

Everyone'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/

No 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-prem 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/

Two 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/

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/

133 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/

Most companies think selling software is enough, but the real shift is owning the outcome.In this episode of the [Un]Churned Podcast, Josh Schachter sits down with Chuck Ganapathi, CEO of Gainsight, live from Pulse 2026 at Caesars Forum in Las Vegas, to unpack why the next era of SaaS isn't about selling seats, it's about delivering results.Chuck shares the thinking behind Gainsight's biggest strategic shift in 15 years, why the build vs. buy debate is a false choice, and how agentic AI is finally making it possible to serve every customer, not just the top 20%.They also dive into:- Why outcome-based services are the future of enterprise software- The "build, buy, or hire" framework redefining customer success- How the long tail of customers has been silently ignored and why that's changing- What human-agent collaboration actually looks like in practice- Why your smallest customers today might be your most strategic accounts tomorrowIf you're leading a SaaS business, scaling customer success, or trying to understand where agentic AI is actually creating leverage, this episode is a front-row seat to the next evolution of this category.---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Chapters00:00 – Intro to Chuck Ganapathi01:45 – Chuck Ganapathi on Taking the CEO Role at Gainsight04:10 – Why Chuck Is an AI Optimist in a Room Full of Doomers07:18 – The One Question Every CEO, CFO & Board Is Asking Right Now09:15 – The False Choice Between Build and Buy11:40 – Announcing Atlas: Gainsight's First AI Native Service14:05 – Why SaaS Has Always Struggled to Prove ROI18:45 – Build, Buy, or Just Hire Gainsight22:50 – The Long Tail Problem Nobody in SaaS Wants to Talk About27:00 – What Humans Actually Do in a Human-Agent Collaboration Model---Where to Find the GuestChuck Ganapathi: https://www.linkedin.com/in/chuckganapathi/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

Everybody can build with Claude now, but nobody figured out the responsibility part yet.Chael Banks runs customer success at Okta. 20,000 customers. Billions of logins a day. In this episode he breaks down a hard rule: his team will never sell. Ever. Why? Trust. In identity security, trust is everything. The moment money becomes the motive, the relationship tarnishes. Chael draws a sharp line between commercials and consulting. His team carries the value narrative instead. He also gets real about the AI supernova. Too much building, not enough consolidation. He shares how Okta uses AI to make people more effective, not just efficient. Plus: the identity maturity model, value realization at scale, the long-tail digital motion, and a personal story about Lane 6 that shaped how he leads.Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com---What You'll Learn- How to split selling from guiding without losing revenue- Why trust beats commission in high-stakes industries- How AI makes junior reps sound senior- The identity maturity model as a value framework- How to scale one consistent conversation across all customer segments- Why efficiency only matters in service of effectiveness- How to run value realization without renewal panic- A leadership lesson on grit from Lane 6---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Timestamps0:00 - Preview & introduction1:30 - Overview of Okta & inside their CS org4:08 - Everyone is building with AI. Now what? 6:00 - The identity maturity model explained9:03 - Customers DO NOT want salespeople & why Chael's team will never do commercials13:30 - What's working at OkTa with the 20% AI transformation17:15 - Okta's long-tail digital motion20:10 - Value realization: the train analogy24:00 - Big rocks at Okta & Chael's message on AI & jobs28:10 - Lane 6: grit, persistence, and leadership---Where to Find the GuestChael Banks: https://www.linkedin.com/in/chaelbanks/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

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.Most companies think customer loyalty is about retention but the real metric is referrals.In this episode of the UnChurned Podcast, Josh Schachter sits down with Fred Reichheld the creator of Net Promoter Score (NPS) & Author of Winning on Purpose, to unpack why the companies that grow the fastest aren't just keeping customers happy they're creating customers who bring others with them.Fred shares the origin story behind NPS, why traditional customer satisfaction metrics failed, and how referral-driven growth became the hidden engine behind some of the world's most successful businesses.They also dive into:- The moral principles behind enduring companies- Why referrals matter more than repeat purchases- How customer experience connects directly to shareholder value- The viral nature of trust and word of mouth- Why entrepreneurs should obsess over “bring your friends” growthIf you're building a business, scaling customer success, or trying to create real word-of-mouth momentum, this episode is a masterclass in profitable growth.Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com---Timestamps00:00 – Intro to Fred Reichheld & the Origins of NPS02:05 – The Hidden Pattern Behind the World's Best Companies04:32 – “Back for More and Bring Your Friends”07:18 – Why Customer Satisfaction Metrics Failed10:41 – The Moral Foundation of Great Businesses14:05 – How NPS Went Viral Before Social Media17:12 – Why Trust Still Drives Buying Decisions20:46 – The Real Economics Behind Referrals24:18 – Investing Based on Net Promoter Scores28:02 – Why Referrals Are the Ultimate Growth Engine---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find the GuestFred Reichheld: https://www.linkedin.com/in/fredreichheld/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

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.Most CS teams are stuck in a loop. Monitor the health score. Chase the red account. Run the QBR. Hope the renewal sticks. Adnan Rahman saw the loop. And broke it.As the Head of Customer & Partner Success at Paycor, Adnan manages 35,000 customer relationships across different segments with a team of nearly 100 CSMs. That kind of scale forces clarity fast. And what became clear? The problem was never the metrics. It was the conversation.In this episode, Adnan breaks down the value realization framework his team built from scratch that is now deployed across 28 enterprise CSMs and 17 mid-market CSMs, with a goal of 75% active success plans by year end. He gets into the exact discovery questions that replaced fear with candor, why executives are now showing up to meetings they used to skip, and how joint success plans replaced the product demo masquerading as a QBR.Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com. ---Timestamps0:00 - Preview & introduction1:17 - Meet Adnan Rahman & Overview of Paycor4:50 - The value realization framework explained7:07 - Do customers arrive knowing their outcomes?8:05 - Bob London's UBR method & the most disruptive questions CSMs ask9:06 - Implementing the framework & outcomes11:56 - How to build your own value framework from scratch16:31 - How Paycor is drawing insights & enhancing efficiency with AI 18:38 - Paycor's agentic future: renewals, expansions, risk20:40 - Paycor's learning & community inititative24:29 - Where Paycor CS is headed by year end---What You'll Learn- How to build a value realization framework- The exact disruptive questions that unlock executive conversations- What a joint success plan looks like vs a traditional QBRHow to connect every CSM touchpoint back to measurable business outcomes- How to ask about renewal without making it awkward- Where AI agents will hit CS teams first- What community looks like when answer engines exist- How to scale personalized outreach without scaling headcount---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find the GuestAdnan Rahman: https://www.linkedin.com/in/adnan-rahman-irvine/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

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.Most people in tech are sprinting toward AI. Scott Barker, Partner & MD at Enfold Institute, Ex-Partner at GTMfund, and the youngest director in Outreach history, is among the few who stopped, looked back, and said: I've seen where this road ends.He was the youngest director in Outreach history. Helped take the company from $20M to $250M ARR. Built a venture fund to $100M under management. Then walked away from all of it, not for a sabbatical, not for a rebrand. Because it was breaking him.Four months in Indian ashrams. Ten hours of meditation a day. No phone, no fund, no identity.What he came back with isn't a mindfulness pitch. It's a strategic argument: the AI era is about to force the entire tech industry into the same acceleration decade that nearly destroyed him. And unlike his, yours won't be a choice.This episode is the conversation the industry needs to have and keeps skipping over to talk about agents.---Timestamps0:00 - Preview & introduction2:07 - Meet Jenny Calvert & Scott Barker 3:35 - Scaling GTM Fund to $100M and why it wasn't enough6:33 - How to Prepare for the Next Decade (The viral article)10:28 - Strategy 1: Slowing down as strategy (the 6-hour silence block)16:50 - Strategy 2: Build depth, not route skills20:33 - The future of currency22:30 - Strategy 3: Train your nervous system daily25:33 - Give yourself permission 29:55 - Challenge your old programming & redefine success34:14 - Final takeaways + close---What You'll Learn- Why AI acceleration is a forced decade of chaos and how to build a foundation before it hits-The 6-hour silence block and why your brain produces better output without inputs- Why skills are becoming a commodity and the one thing AI still can't replicate- How to identify and dismantle the old programming driving your definition of success- The daily non-negotiable practice (movement, stillness, breath, solitude) that trains your nervous system for chaos- Why the next scarce currency isn't money---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find the GuestScott Barker: https://www.linkedin.com/in/ssbarker/Scott's Substack Article: https://thewakeupcallnewsletter.substack.com/p/how-to-prepare-for-the-next-decade---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

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/

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.When your customer success org covers all of Azure — Microsoft's $60B+ cloud business — "deployment" isn't a checkbox. It's a global operation spanning thousands of projects, 180+ people, and a fully invested delivery model where Microsoft does the first leg of the journey for free.Pradeep Raman, Vice President, Customer Success at Microsoft, breaks down Microsoft's "commit to consume" metric, why they staff at N-1 by design, how agentic AI is replacing intake teams internally, and why no customer celebrates signing a contract — only deploying one.Pradeep who has spent over 27 years with Microsoft started in consulting, learned new tech on plane rides to customer sites, once asked Bill Gates to pin a customer's logo to his shirt (security wasn't thrilled), and now runs the CS strategy and Cloud Accelerate Factory for Azure.---Timestamps0:00 - Preview & introduction1:24 - Meet Pradeep Raman & his 27-year run at Microsoft3:25 - The Bill Gates pin story4:30 - What "VP of CS" means at Microsoft's scale6:45 - Cloud Accelerate Factory: free deployment for all Azure customers10:45 - "No customer celebrates signing an agreement"11:48 - Goal-setting & OKRs: Commit to Consume & Next Best Action15:25 - Agentic AI and modernization as top priorities16:37 - Building AI enablement inside the CS team20:40 - "I didn't think I'd survive 20 minutes of the interview"---What You'll Learn- How Microsoft measures CS with a single "commit to consume" KPI — and why it changes everything- What the Cloud Accelerate Factory is and why Microsoft offers free hands-on deployment to any Azure customer- Microsoft's N-1 staffing philosophy: hire fewer people than needed, then make it work- How Pradeep's team is using custom agentic AI (analyst agents, architect agents) to scale internal processes- Why AI transformation fails when your data and apps sit in legacy environments- The evolution of CS at Microsoft — from sales support function to growth engine---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find the GuestPradeep Raman: https://www.linkedin.com/in/pradeep-raman-41a12a11/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

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.When healthcare equipment goes down, healthcare goes down. That's the world Brad Casemore operates in — where a broken MRI or a failed sterilization unit isn't an inconvenience, it's a crisis.In this episode, Brad, Chief Customer & Growth Officer at PartsSource breaks down why merging the CCO and CGO roles actually makes sense. He makes the case that customer value and revenue growth are the same motion, not separate departments, and walks through exactly how he's built his org to reflect that. If you're a CS leader wondering whether you should own more of the business, this is the episode.Brad also shares how he's plugging AI agents directly into the RACI model — not as a gimmick, but as a deliberate workforce strategy. Humans accountable, agents responsible. The result? One part of his business went from low-90s retention to 99.6%. This is what the future of CS operations actually looks like in practice.---Timestamps0:00 - Preview & introduction1:24 - Meet Brad Casemore & overview of PartsSource4:17 - The marketplace, service network, training, and predictive monitoring explained10:46 - Post-sales inside a 750-person company with a surprisingly complex portfolio13:17 - The CCO + CGO role; why Brad took it and what changed15:55 - Key learnings from stepping into the growth seat17:57 - The attribution model CS leaders need to steal from sales19:45 - Putting AI in the RACI: how Brad's team went from low-90s to 99.6% retention25:15 - Systems thinking, curiosity, and getting comfortable being uncomfortable28:02 - Pulse 2025 and what Brad's watching in AI---What You'll Learn- When CCO and CGO roles merge and the org structure to make it work- How to map the full customer lifecycle so pre-sales and post-sales are pulling in the same direction- The attribution lesson CS leaders are missing that sales and marketing figured out years ago- How to build a consistent customer experience across a long-tail of thousands of accounts without burning out your team- Why Brad puts AI agents directly into the RACI model — and what that means for team design- The proactive CS shift that moved retention from the low-90s to 99.6%- What aspiring CS leaders need to develop to grow into an executive seat ---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find the GuestBrad's LinkedIn: https://www.linkedin.com/in/bradocasemore/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

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.Knowledge used to be the CSM's edge. Not anymore.Diane Wu, Global Head of Customer Success & Experience at Google Cloud Security, operates where every touchpoint is mission-critical — and standing still is falling behind. In this episode, she sits down with Brady Bluhm & Josh Schachter of Gainsight to unpack what the CSM role actually becomes when AI handles the knowledge layer. The answer: context, curation, and hyper-personalization at scale.Diane shares how her team is using NotebookLM and Gemini to compress hours of customer research into minutes, why her best CSMs were the hardest to get onto new AI tools (and why that makes complete sense), and what two-phase AI adoption really looks like on the ground. Brady brings a builder's lens — talking about juggling AI agents, closing 2-year-old CTAs with one prompt, and why the traditional product UI might not survive the next two years.If you lead a post-sales team or work in customer success, this conversation will reframe how you think about productivity, coverage models, and the human role in an AI-first world.---Timestamps0:00 - Preview & introduction1:40 - Meet Brady Bluhm (Gainsight) & Diane Wu (Google)3:00 - Diane's role: Google Cloud Security & the post-sales mission5:25 - The shift from access to curation8:28 - Brady: how AI is changing CSM onboarding and memory10:55 - Are you saving time or just doing more? 12:34 - How AI changes coverage models and the 1:many CSM ratio18:00 - Diane's tactical playbook for running parallel customer analyses 22:05 - Brady's "can I do this with AI?" framework and skill-building loop24:00 - How much time should you spend tuning your AI setup?26:31 - Why your top CSMs are the hardest to get on new AI tools31:21 - LLMs will become the new workspace32:59 - Two-phase LLM adoption and why the UI is going away34:15 - Closing 2-year-old CTAs with one prompt37:47 - Hyper-personalization at scale for Google Cloud---What You'll Learn- Why knowledge is no longer the CSM's differentiator — and what replaces it- How Diane's team at Google Cloud Security uses NotebookLM as a living customer notebook- Why your best CSMs resist AI adoption the most- How AI is reshaping CSM coverage models and the 1:many ratio- Brady's two-question AI habit that keeps him ahead every week- What the Gainsight MCP unlocked — and what it means for the future of CS tooling- Why the traditional application UI may disappear — and what replaces it- How to create "wow moments" that actually drive AI adoption across your team---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find the GuestsDiane Wu's LinkedIn: https://www.linkedin.com/in/diane-wu/Brady Bluhm's LinkedIn: https://www.linkedin.com/in/bradybluhm/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

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.Watch Eric Gilpin, President of Go-To-Market at G2, reveal how he's building the first-ever unified revenue org in a 210,000-product marketplace. In this episode, he takes us behind the scenes of G2's “zero daylight” alignment strategy and how it led to a game-changing 31% YoY traffic spike. Discover why G2 made the controversial bet to let LLMs scrape their data (and why competitors are now paying the price), how to flip buyer intent into “churn intent” to catch customers before they leave, and how the difference between “freelancers” and “contractors” became worth $600M+ in revenue. This is marketplace strategy 101, told by someone who's spent 25+ years perfecting it. Essential listening for GTM leaders, CS teams, and anyone building in B2B SaaS.---Timestamps0:00 - Preview & introduction1:28 - Meet Eric Gilpin & overview of G26:50 - How Upwork scaled from $30M to $650M in gross sales volume10:00 - Building G2's first President of Go-To-Market role11:13 - Zero daylight: Aligning marketing, BDRs, and all revenue teams16:42 - Pivoting narrative from “SEO review site” to AEO visibility engine18:15 - G2's “Hunter Hunter” post-sales org (60% growth from expansion)21:00 - The highest-value CS activities (hint: it's not quarterly review sends)23:23 - Self-serve + AI automation for the 150,000 SMB products25:23 - The churn intent27:28 - Why G2 allowed LLMs to train on their data31:55 - Nostalgia and denial kill businesses---What You'll Learn- How to eliminate silos by achieving “zero daylight” between marketing, sales, and revenue teams- The whitespace model G2 uses to find expansion revenue- How to build a “churn intent” system using buyer signals to catch churn before it happens- Why allowing LLMs to scrape your data early creates a competitive moat- The subtle power of reframing to unlock enterprise adoption and market perception- Why is constantly challenging your own status quo the only defense against disruption---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find Eric GilpinLinkedIn: https://www.linkedin.com/in/ericgilpin/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

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.What does the future of CS actually look like? Ghazi Masood, CRO of Replit, has some strong opinions and the growth numbers to back them up.In one year, Replit went from $2M to $150M in revenue. Now they're targeting $1B. And while most companies are still debating AI strategy, Ghazi is already rebuilding his entire GTM org around it — scaling from 40 to 230 people, scrapping the traditional CSM model, and betting that the next billion software creators won't write a single line of code.In this episode, Ghazi breaks down how he's building post-sales for the AI era, why he replaced CSMs with "product advocates," and what it looks like when your entire team builds their own tools — including their own version of Clari and a customer health dashboard, both built on Replit itself.He also shares his take on the future of SaaS, how enterprises are quietly wrapping AI layers on top of Salesforce and Workday, and why Cursor, Claude, and OpenAI aren't keeping him up at night.If you're in Customer Success, Revenue, or CS Ops, this episode will challenge how you think about your role.---Timestamps0:00 - Preview & Introduction1:25 - Meet Ghazi Masood & Overview of Replit4:40 - Building the GTM infrastructure7:30 - How anyone at Replit can build internal tools9:00 - Managing chaos when everyone becomes a creator12:40 - Enterprise security & governance guardrails15:47 - Are Cursor, Claude & OpenAI real competitors?18:10 - Usage-based pricing explained19:17 - Post-sales strategy for non-technical users23:53 - Hiring 200 people in 12 months24:40 - The future of SaaS26:56 - SMBs replacing Workday and Tableau with Replit30:40 - Lessons from Auth0 and Retool32:32 - What Ghazi looks for when hiring---What You'll Learn- What enterprise customers are quietly building on top of their existing SaaS tools — and what it means for vendors- How SMBs are replacing Workday, Tableau, and traditional CRMs entirely by building on Replit- How to handle churn when 90% of your users have zero technical background- The governance and security guardrails that got Replit into financial services and government accounts- How to structure a GTM catalog library so your team stops duplicating each other's work- Ghazi's take on whether SaaS is dying — and why the answer is completely different depending on company size- Why product passion matters more to Ghazi than years of sales experience when hiring- How Replit thinks about competitive threats from Cursor, Claude Code and OpenAI — and why they're not losing sleep over any of them---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find Ghazi MasoodLinkedIn: https://www.linkedin.com/in/ghazi-masood-09195a2/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

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.CS is going through an identity crisis. Is it product? Is it relationships? Is it revenue?According to Cassie Vaughn (RVP of CS at monday.com)… it's now all three, and AI is forcing it to be so. In this episode of Unchurned, Cassie breaks down what's actually changing inside modern CS orgs after scaling from CSM to leading a 100+ person team—and why most companies are still getting it wrong.You'll hear why “value” is still more storytelling than science, why health scores can't be trusted, and why the future CSM won't just manage customers… they'll manage agents.But here's the twist: as AI automates more of the work, the human side of Customer Success is becoming even more critical. Monday.com is literally doubling down on time spent with customers—while everyone else is trying to scale it away.Cassie also shares the bold bet they made: turning CSMs into revenue owners with variable comp—and why, in a consumption world, CS might actually be more commercial than sales.---Timestamps0:00 - Preview & Introduction1:10 - Cassie's journey from being a CSM to RVP4:15 - What's changed in CS over the last 6 years6:13 - Why measuring customer value is still broken9:35 - Why monday.com doubled time with customers12:37 - The rise of the “agent manager” CSM14:07 - Scaling CS with AI vs human touch16:47 - Why CSMs are more commercial than sales18:10 - Challenges of shifting to revenue ownership19:30 - Why CSMs should think commercially & not trust health scores21:50 - Stop being a generalist: career advice23:26 - AI fluency as the #1 priority for 202625:25 - Lightning round: F1, food, and fun---What You'll Learn* Why has no one cracked customer value measurement* How to build value narratives that actually land with executives* What AI should automate—and what should stay human* Why the future CSM is an “agent manager”* How monday.com is doubling customer time in an AI era* Why CSMs should be more commercial than sales* How to introduce variable comp for Customer Success* Why health scores are not enough (and what to do instead)---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find Cassie VaughnLinkedIn: https://www.linkedin.com/in/cassiebrown/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

Ready to churn less and win more?

Ready to churn less and win more?

Ready to churn less and win more?

Ready to churn less and win more?

Ready to churn less and win more?

Ready to churn less and win more?

Ready to churn less and win more?

Ready to churn less and win more?

Ready to churn less and win more?

Ready to churn less and win more?

Ready to churn less and win more?

Ready to churn less and win more?

Ready to churn less and win more?

Ready to churn less and win more?

Ready to churn less and win more?

- Ready to churn less and win more?

Ready to churn less and win more?

Ready to churn less and win more?

When the Chief Customer Officer role first emerged in SaaS, Alexis Hennessy was already there—helping define it. Twelve years ago, she co-founded the post-sales executive search practice inside Heidrick & Struggles, one of the world's premier search firms. She witnessed the rise of the CCO, the collapse of the role during the downturn, and now the fastest resurgence the market has seen in years.In this episode, Alexis breaks down why retention has become existential, why CCO hiring has spiked again, and what the best CCO candidates consistently do to stand out. She details the patterns behind successful hires, the emergence of consumption and AI-driven operating models, and why the path from CCO to CEO may finally be opening wider than ever.A practical and unfiltered look into the future of post-sales leadership—from the person helping shape who gets the top jobs.---Timestamps0:00 – Preview & Introduction1:22 – Meet Alexis Hennessy: Partner at Heidrick & Struggles2:02 – Many CEOs Still Don't Know What They Want4:10 – What CEOs Want in a CCO5:16 – What Great CCO Candidates Do in Interviews6:15 – Why CCO Hiring Is Surging Again7:25 – What Sets VP Candidates Apart When They Want to Move Up9:00 – Are Boards Demanding AI Experience? 10:45 – What the Best CCO Hires Do in Their First Year12:45 – Personality Traits That Define High-Performing CCOs13:43 – Agentic AI, Consumption Models & the New Stakes for CCOs15:23 – Can CCOs Become CEOs? 18:28 – Predictions: The Future of the CCO Role19:23 – Closing Thoughts---What You'll Learn* Why the CCO role is surging again after a multi-year slump* The three types of CEOs who hire CCOs—and which ones to avoid* The interview behaviors that separate top candidates from the rest* Why “listening first” is the #1 predictor of CCO success* What VPs need to show to break into the CCO ranks* The business conditions making the CCO-to-CEO path more realistic than ever* The critical KPIs great CCOs build to influence their executive peers* How consumption and agentic AI models increase the strategic importance of retention---Check out the Key Takeaways & Transcripts: https://www.gainsight.com/presents/series/unchurned/---Where to Find Alexis:LinkedIn: https://www.linkedin.com/in/alexishennessy/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/

When Erica Kuhl joined Salesforce as employee #176, nothing about her role or title suggested she would go on to build one of the most influential customer communities in SaaS history. Given a broken website, no roadmap, no team, she hacked together the first Salesforce Community with duct-taped technologies, raw conviction, and a fierce belief that customers needed a place to help each other.That grassroots experiment eventually grew into a 17 million-member global community, became a blueprint for digital customer success, and reshaped the way enterprise SaaS companies think about adoption, retention, and product feedback loops.Today, Erica is EVP & GM at Gainsight, leading community, education, and in-app product experience—and shaping the emerging category of Digital Customer Success.This episode is a masterclass in community-powered retention, scrappy innovation, and how one person can build an entirely new motion inside an organization long before the market knows it needs it.---Timestamps0:00 – Preview 0:58 – Meet Erica Kuhl: EVP at Gainsight & Former Employee #176 at Salesforce3:39 – What Early Salesforce Adoption Actually Looked Like6:25 – Teaching Admins Before Admins Existed9:40 – Why Erica Pitched a Community Before “Community” Was a Thing11:25 – Building the First Salesforce Community13:43 – Scaling Without Support19:30 – How Community Became a Strategic Retention Lever 24:44 – Defining Digital Customer Success26:35 – Where to Start: Crawl–Walk–Run for Digital CS30:25 – Why Community Multiplies GRR31:28 – Closing Thoughts---What You'll Learn- How the first modern SaaS community was built—from scratch, without buy-in- Why peer-to-peer engagement scales support, adoption, and product feedback- How to tie community engagement directly to retention (and why it's essential)- Why COVID reshaped the priority of customer marketing and always-on programs- How community, education, and in-app experiences converge into Digital CS- Where digital CS programs should start and how to avoid fragmented experiences- The cultural mindset needed to build community programs that actually survive- Practical tactics for early-stage community building: seeding, puppeteering, protecting, and aligning---Check out the Key Takeaways & Transcripts: https://www.gainsight.com/presents/series/unchurned/---Where to Find Erica:LinkedIn: https://www.linkedin.com/in/ericakuhl/Podcast: In Before the LockWhere to Find Josh: LinkedIn: https://www.linkedin.com/in/jschachter/---Resources Mentioned:* Gainsight Community* Brian Oblinger's Community Strategy Academy* Skilljar * Salesforce Community

When Cloudbeds faced a post-sales organization at 120% capacity, no budget, and declining efficiency, Colin Slade chose to rebuild the operation through AI. Within nine months, his four-person AIOps team deployed more than 150 workflows and agents, automating 75% of repetitive work and reclaiming 7,000 hours every month.This episode details how Colin turned a resource-starved customer success organization into an AI-driven engine. It explores the early missteps, the shift from overengineering to small, quick wins, and how incremental adoption evolved into company-wide transformation.A practical study in applied AI, organizational change, and measurable outcomes—showing how constraint, not abundance, can drive real innovation.Timestamps0:00 – Preview & Introduction0:57 – Meet Colin Slade and the Situation at Cloudbeds9:25 – Mitigating Team Fears Around AI Replacing Jobs13:13 – The Stepwise Approach to Implementing AI19:50 – Scaling Securely: Working with IT, Risk-Taking, and Adoption24:00 – Roles and Team Structure for Effective AI Operations33:10 – Documentation as a Hidden Bottleneck39:45 – Build vs. Buy: Why Cloudbeds Built In-House42:20 – The Impact and a Culture of Fearless ExperimentationWhat You'll Learn* How to rebuild a post-sales org around AI without additional headcount* The step-by-step approach to deploying 150+ workflows in under a year* How to identify and structure AI roles: visionary, operators, knowledge masters, and project leads* The cultural and psychological levers for AI adoption* How to optimize documentation for AI readability (and boost SEO at the same time)* The measurable impact of AI on cost savings, efficiency, and morale---Check out the Key Takeaways & Transcripts: ⁠https://www.gainsight.com/presents/series/unchurned/⁠---Where to Find Colin:LinkedIn: ⁠https://www.linkedin.com/in/colinslade/Where to Find Josh: LinkedIn: ⁠https://www.linkedin.com/in/jschachter/⁠---Resources: n8n – https://n8n.io/Forethought – https://forethought.ai/Google AI Studio – https://aistudio.google.com/Anthropic Claude – https://claude.ai/Gemini – https://gemini.google.com/appLovable – https://lovable.dev/Pinecone – https://www.pinecone.io/Snowflake – https://www.snowflake.com/en/Zendesk – https://www.zendesk.nl/Salesforce – https://www.salesforce.com/Slack – https://slack.com/

Why most enterprise AI fails — and how Cat Valverde's 4-week adoption framework shows that the fix is just 15 minutes a week.Most enterprises are stuck in AI pilot purgatory — running endless experiments that never scale. In this episode of Unchurned, Josh Schachter sits down with Cat Valverde, founder of Enterprise AI Group, to break down what's really blocking enterprise adoption.Cat shares her research-backed 15-Minute Rule, a simple 4-week framework that's doubled or tripled adoption rates — all by making AI implementation human-centered instead of tool-centered.If you're a leader trying to take AI from pilot to production, this is your playbook.What You'll Learn- Why most enterprise AI initiatives fail to scale past pilot stage- How to reduce adoption friction and create lasting behavior change- The psychological levers that improve user buy-in and learning retention- How to structure a simple 4-week rollout for any AI tool or workflow- What metrics actually matter when evaluating AI adoption successTimestamps: 0:00 – Preview & Intro1:02 – Meet Kat Valverde 1:42 – What buyers and sellers say in enterprise AI roundtables3:11 – The challenge of internal adoption 6:20 – The 15-Minute Rule; a 4-week micro-adoption framework11:45 – The psychology behind AI adoption12:18 – 2–3× adoption rates and major cost savings14:45 – Closing thoughtsKey Takeaways- Pilot fatigue is real — the biggest blocker to enterprise AI adoption isn't money, it's time and cognitive load.- The true KPI: internal adoption, not just model accuracy or ROI.- Fear ≠ just job loss. It's the fear of asking “dumb” questions or not keeping up with peers.- The 15-Minute Rule: a 4-week program built on psychology that uses micro-commitments to build momentum.- Outcomes: 2–3× higher adoption and ~50% training-cost reduction per user.---Check out the Key Takeaways & Transcripts: ⁠https://www.gainsight.com/presents/series/unchurned/⁠---Where to Find Cat:LinkedIn: ⁠https://www.linkedin.com/in/catvalverde/Enterprise AI Group: https://www.eais.io/Where to Find Josh: LinkedIn: ⁠https://www.linkedin.com/in/jschachter/⁠---Resources: The Power of Habit: https://www.charlesduhigg.com/the-power-of-habit

The Biggest GTM Mistake (Spoiler Alert: Stop Chasing CAC!!!)Mark Roberge shares how AI is transforming sales, customer success, and go-to-market strategy. The former HubSpot CRO, now co-founder of Stage 2 Capital and senior lecturer at Harvard Business School, Mark Roberge breaks down the 4 phases of AI evolution that will redefine how companies sell, serve, and scale. From agentic AI to LTV-driven growth, this is a masterclass on what the next era of go-to-market looks like.Mark Roberge helped take HubSpot from $0 to $100M and literally wrote The Sales Acceleration Formula. Now, he's turning his attention to the AI transformation sweeping every GTM function. In this episode, Mark explains why it's time to stop obsessing over CAC and start optimizing for LTV—the customers who actually succeed—and how AI can make that possible at scale.He also shares bold predictions about the future of work, the death of departments, and why capitalism itself may need to evolve for the AI era.Timestamps0:00 – Preview & Introduction1:19 – Meet Mark Roberge: Co-Founder, Stage 2 Capital2:45 – The Early Days of AI in GTM6:33 – What's Slowing Down AI Adoption8:00 – Why Most AI Startups Are Still Too Iterative12:00 – The "Agentic" Shift: From Co-Pilots to Autonomous Agents14:15 – The 4 Phases of AI Go-to-Market Evolution20:35 – Managing Your Agents: The New CRO Skillset26:00 – Deciding the ICP: It's Not CAC29:35 – How AI Breaks Down Department Silos35:40 – Can Capitalism Survive the AI Era?46:00 – The Science of Scaling: Mark's Next Big Book---What You'll Learn* Why CAC is the wrong north star metric for GTM leaders* How to use AI to identify and retain high-LTV customers* The 4 phases of AI transformation in go-to-market* How agentic AI will redefine the roles of CROs, CSMs, and RevOps* Why AI will blur departmental boundaries and change the structure of business* How capitalism and work culture must evolve in the AI era---Check out the Key Takeaways & Transcripts: ⁠https://www.gainsight.com/presents/series/unchurned/⁠---Where to Find Mark:LinkedIn: ⁠https://www.linkedin.com/in/markroberge/Where to Find Josh: LinkedIn: ⁠https://www.linkedin.com/in/jschachter/⁠---Resources mentioned:* Stage 2 Capital Blog – Go-to-Market AI Case Studies: https://www.stage2.capital * The Sales Acceleration Formula by Mark Roberge

Jacob Bank has been building AI agents since before they were cool. While the rest of us were just figuring out what ChatGPT could do, Jacob was already 13 years deep into agent research. Now, as founder and CEO of Relay.app, Jacob is making AI agents accessible to everyone, from customer success teams to businesses that install slip-resistant floors. Jacob has a fascinating prediction: within a year, agents will be able to handle virtually any task you do on your computer. The real question won't be "can an agent do this?" but rather "how do I teach, manage, and trust my agent?"Timestamps0:00 - Preview & Introduction1:48 - Meet Jacob & An Overview of Relay.app4:08 - From Stanford AI Research to Google to Founder4:57 - AI Agents were 15 Years in the Making 8:30 - It Took 2.5 Years to Get the First Customer12:35 - What Actually Is Agentic AI?14:55 - Understanding AI Agents19:45 - How AI Accesses Information: Context Windows, and RAG24:11 - The Shift from RAG to MCP25:51 - Understanding MCP: The Restaurant Analogy30:04 - Real-World Use Cases of Workflows with AI for CSMs 33:51 - When and When Not to Use Agents 37:45 - Why SMBs Move Faster on AI Than Big Enterprises42:12 - The Two Limitations of Agents Today44:31 - We're All Managers Now46:15 - Where to Stay Current on AI47:36 - The Value of Hands-On Experience with AI ToolsWhat you'll learn:- The critical difference between workflows and agents (and why you need both)- Why "we're all managers now"—even if you're an individual contributor- The future of work isn't about doing tasks; it's about managing and calibrating your agents- Practical use cases of Agentic AI for CSMs- Why spending an hour daily experimenting with AI tools is "worth its weight in gold"Resources mentioned:- Ben's Bytes newsletter- Jeff Siu (YouTube)

What if the function you were about to join didn't really exist yet?In 2014, customer success was barely a function—it was an idea in the making. Omer Rabin took a bet on that idea at a time when the industry still needed convincing that managing customer relationships deserved its own tech stack. He went on to become Gainsight's Chief Evangelist when most people thought “customer success” sounded like corporate cheerleading.Fast forward a decade, and customer success has grown into a multi-billion-dollar industry. But somewhere along the way, many CS teams drifted from their strategic roots, becoming reactive order-takers buried in grunt work.In this episode, Omer Rabin (General Partner at TLA Ventures) and Chad Horenfeldt (VP of CS at Siena AI and author of The Strategic CSM) discuss the past, present, and future of customer success. They take us back to the early days—Pulse local events on Toronto rooftops, the hunter vs. farmer debate, and how Nick Mehta's pitch about “selling to existing customers” helped create an entire category.WHAT YOU'LL LEARN:• Why customer success emerged as a distinct function (and why it almost didn't)• How CS teams lost their strategic edge—and how to reclaim it• Why AI is bringing CS back to its strategic roots by eliminating grunt work• Why Omer believes the next generation of CEOs will come from customer success• Chad's framework for future customer intelligence• The one question every CSM should ask to align with their CEO's top priority---Check out the Key Takeaways & Transcripts: https://www.gainsight.com/presents/series/unchurned/---Where to Find Chad:LinkedIn: https://www.linkedin.com/in/chadhorenfeldt/The Strategic CSM: https://www.strategiccustomersuccess.com/Where to Find Omer:LinkedIn: https://www.linkedin.com/in/omerabin/Where to Find Josh: LinkedIn: https://www.linkedin.com/in/jschachter/--- In this episode, we cover:0:00 – Preview & Introduction1:24 – Meet Chad & Omer2:10 – Pulse Local Events and Building the CS Community3:52 – Chad's Origin Story: Being an Early CS Ambassador4:55 – From Customer Cheerleading to Value Creation12:45 – The AI Revolution and the Return of Strategic CSMs18:31 – How Outcome-Based CS Influences Revenue23:53 – Defining Success Is a Challenge25:25 – How AI Analyzes Survey Data to Find Customer Sentiment28:10 – Customizing Product Updates for Customers29:25 – Tactical Advice for CSMs30:35 – Aligning with Company Needs

The best product leaders don't start in product—they start in customer success.Nick Mehta, former Gainsight CEO, sits down with PathFactory's CPO & CCO, Venk Chandran, who built his product career from the ground up in CS. Venk reveals why working backwards from renewals changes everything, how CS teams can drive AI adoption with their customers, and why websites are dying in the age of AI agents. Plus: the art of asking better questions, the emotional differences between CS and product roles, and what we owe our customers in the era of AI.WHAT YOU'LL LEARN:- Why starting your career in renewals teaches you to work backwards from value- How customer success is fundamentally a financial business (and why that matters)- Why AI agents are replacing websites as the primary B2B buying experience- How to help customers adopt AI when they're used to manual workflows- The difference between outbound and inbound product managers (and why you need both)- Why is delayed gratification in product harder than the instant wins of CS- How to retrain yourself (and your customers) to ask better questions of AI---Check out the Key Takeaways & Transcripts: https://www.gainsight.com/presents/series/unchurned/---Where to Find Venk:LinkedIn: https://www.linkedin.com/in/venkchandran/Where to Find Nick:LinkedIn: https://www.linkedin.com/in/nickmehta/Where to Find Josh: LinkedIn: https://www.linkedin.com/in/jschachter/--- In this episode, we cover:0:00 - Preview & Introduction 1:10 - Venk's Journey From Radio Waves to Product Leadership 7:37 - How Venk Jumped From HR Tech → Sales → CS → Product (and Made It Work)10:32 - Learning at Salesforce: The Surprising Lesson Venk Learned From Renewals12:05 - Why CS Is a Financial Business First — The Real Definition of Customer Value15:19 - CS to CPO: 3 Game-Changing Skills That Make the Transition Possible17:05 - CS vs. Product: The Emotional Shift No One Talks About19:51 - PathFactory's Big Vision — Connecting Content Directly to Revenue (With AI!)22:28 - Why Websites Are Dying — And What's Replacing Them25:35 - Truth, Transparency & Trust: What We Owe Each Other in the AI Era26:51 - The AI Adoption Problem: Why CS Teams Struggle With Change Management31:35 - The Art of Asking Better Questions ---Referenced:Salesforce - https://www.salesforce.com/Perplexity - https://www.perplexity.ai/ChatGPT - https://chat.openai.com/

How do you manage 100,000+ renewals or scale AI across thousands of CSMs? CS leaders share how they're tackling their biggest challenges and using technology to drive retention, adoption, and efficiency.In this episode of the [Un]churned Podcast, Josh Schachter sits down with customer success leaders at the 2025 Gainsight Pulse Conference in Las Vegas to explore how they're tackling their biggest challenges - from managing massive renewal volumes to driving adoption at scale. Featuring CS executives from Rockwell Automation, Fleetio, Handshake, Boomi, Dellteck, and SAP, this episode reveals practical strategies for using AI to save time, improve efficiency, and deliver better customer outcomes.What you'll learn:1. How Rockwell Automation's CS team manages 100,000+ annual renewals with 300 team members across 85 recurring revenue products2. Why AI-powered engagement signals are replacing time-based customer outreach3. The importance of building trust in AI-powered insights before teams will adopt them4. How to aggregate and visualize data from multiple systems to tell a coherent story to stakeholders5. Why change management is critical when introducing new product features that alter established workflows6. How relationship-level insights can reveal the full picture of multi-product customer health---Check out the Key Takeaways & Transcripts: https://www.gainsight.com/presents/series/unchurned/---Where to Find the guests:- Angel Rogers - https://www.linkedin.com/in/angel-rogers-leader/- Sean MacPherson- https://www.linkedin.com/in/seanmacpherson- Tiffany Taylor - https://www.linkedin.com/in/tiffany-taylor-learner/- Matt Krebsbach - https://www.linkedin.com/in/matt-krebsbach-694117163/- Charlie Ferraro - https://www.linkedin.com/in/charlesferrao/- Margo Martin - https://www.linkedin.com/in/margomartin-/- Tony Pante - https://www.linkedin.com/in/tony-pante-9b5419/---Where to Find Josh: LinkedIn: https://www.linkedin.com/in/jschachter/--- In this episode, we cover:0:00 - Introduction 0:27 - Angel Rogers: Managing 100K renewals at Rockwell Automation5:32 - Sean MacPherson: Aggregating insights from multiple systems9:48 - Tiffany Taylor: Speed up feedback loops and time-to-value14:09 - Matt Krebsbach: Prioritization, delivering outcomes and data enablement 18:47 - Charlie Ferraro: Retention, renewals and efficiency20:35 - From Spidey sense to AI-powered engagement analysis21:47 - Measuring adoption in agentic products22:07 - Margo Martin: Stay ahead with real-time defect alerts25:17 - The value of relationship-level insights26:10 - Tony Pante: Driving adoption across 2,000 CSMs at SAP29:35 - Using AI for translation, content creation, and enablement---Referenced:• Gainsight Pulse Conference: https://gainsightpulse.com/europe/• Rockwell Automation: https://www.rockwellautomation.com/• Fleetio: https://www.fleetio.com/• Handshake: https://joinhandshake.com/• Boomi: https://boomi.com/• Dellteck: https://www.deltek.com/en• SAP: https://www.sap.com/• Staircase AI: https://www.gainsight.com/staircase-ai/• Reef AI: https://www.reef.ai/• Gong: https://www.gong.io/de/• SAP Joule: https://www.sap.com/products/artificial-intelligence/ai-assistant.html

"How Agentic AI Is Replacing Subscription Revenue"Chuck Ganapathi, the CEO of Gainsight & Brett Queener, Managing Director at Bonfire Ventures, who previously ran product at Salesforce and helped destroy Siebel, the company where he and Chuck first met. Together, they've witnessed every major shift in enterprise software over three decades, and they believe the biggest one is happening right now.In this conversation, Brett unveils his forthcoming thesis on "the end of ARR," arguing that agentic AI will fundamentally break subscription business models. When products finally achieve what he calls "product purity", actually doing the job they promise without requiring armies of CSMs, endless onboarding, and quarterly business reviews, the entire economic foundation of SaaS collapses. Chuck and Brett discuss whether this is an existential threat or the evolution the industry has been waiting for.What you'll learn:- Why the "friction gap" between product and value created the entire CS industry- What "product purity" means and why it threatens traditional SaaS economics- How agentic AI fundamentally changes the unit economics of software- Why usage-based pricing is inevitable once products actually work- The product marketing playbook that still matters in an AI-first worldCheck out the Key Takeaways & Transcripts: https://www.gainsight.com/presents/series/unchurned/Where to Find the GuestBrett's LinkedIn - https://www.linkedin.com/in/brettqueener/Chuck's LinkedIn: https://www.linkedin.com/in/chuckganapathi/Where to Find Josh: LinkedIn: https://www.linkedin.com/in/jschachter/In this episode, we cover:0:00 - Preview & Introduction1:18 - Meet Chuck & Brett3:30 - How Brett and Chuck met at Siebel 9:28 - Transition to Salesforce: destruction of Siebel as a goal14:11 - Changing Nature of Product Marketing in the AI Era18:00 - Systems of Record vs. Systems of Action21:13 - Databases as “lossy” representations of reality29:00 - Brett's thesis: "The End of ARR (And I Feel Fine)"34:28 - How should agentic applications be priced?43:43 - Future Outlook: Market paying premium for top agents47:17 - 10x CSMs enabled by AI agentsReferences:- Brett Queener's blog: https://queener.substack.com/