[Un]Churned – The No. 1 Podcast for Customer Retention

Hosted by Gainsight

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229

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Nov 2026

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About the show

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.

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November 11, 2026Episode 21748 min

Why CSMs Need Equanimity, Not Positivity ft. Kevin Bailey (Dreamfuel)

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com . Your customer says they’re not renewing. Your heart races, you stop breathing, and the only thing you want is to get off the call. Kevin Bailey, co-founder & CEO of Dreamfuel and a mental performance coach with a master’s in applied neuroscience, says that reaction is physiology, not personality, and that it can be trained. Kevin brings the playbook used by pro athletes and military operators to post-sales leaders. He explains why AI is making leadership more mentally draining by stripping out calm, low-effort work and leaving a day full of rapid, high-stakes decisions. He maps the four states your nervous system cycles through, shows how fight, flight and freeze responses quietly make your decisions for you, and explains why equanimity is the state top performers from Michael Jordan to Navy SEALs train for. Then it gets practical: a 30-breath reset you can do before a tough QBR, how to stay steady during a churn conversation, a one-line reframe that keeps you composed, and the morning rehearsal journaling method Kevin credits with raising his close rate. He also shares the story of losing his biggest customer and why it became the turning point for his company. --- What You'll Learn - Why AI is increasing decision fatigue and mental exhaustion for CS and post-sales leaders, not reducing it - The four nervous-system states and how to recognize which one you’re in during a meeting - How a flight response in a tough QBR can lower your thinking power and drain your energy - The 30-breath reset and box breathing techniques for getting centered before high-stakes calls - How to stay calm and compassionate when a customer tells you they’re churning - The “best thing that could have happened” reframe and why it works without being self-deception - How rehearsal journaling uses visualization to shape how you show up each day - How losing a top customer can become a growth catalyst --- Timestamps 0:00 - Preview & Meet Kevin Bailey 1:22 - Overview of DreamFuel 3:55 - Kevin’s freeze response at his first startup 7:32 - The Greenlight Guru turnaround and a 20% close-rate lift 8:39 - The founder roller coaster and equanimity 10:47 - Michael Jordan, Tim Grover and the flu game 13:00 - How AI is causing decision fatigue 15:36 - The science: four nervous-system states 17:24 - Flight response in a tough QBR 20:20 - Freeze, fawn and focus 21:32 - Why equanimity beats every other state 23:12 - The 30-breath reset and box breathing 25:14 - How long the effect lasts 26:18 - Don’t stop breathing on a churn call 28:03 - The “best thing that could have happened” reframe 29:44 - Does your subconscious buy it? 32:35 - Holding form under pressure 33:20 - Post-it notes as mindset cues 34:30 - How stress affects memory 36:57 - Reframing isn’t lying to yourself 37:32 - When your biggest customer churns 39:43 - Neuroplasticity and rewiring beliefs 42:31 - Rehearsal journaling 45:17 - Feel it, then use music to amplify it --- Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com --- Where to Find the Guest Kevin Bailey: https://www.linkedin.com/in/kevinjamesbailey/ --- Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/ Unchurned Substack: https://unchurned.substack.com/

November 4, 2026Episode 21639 min

Why Every CSM Needs Commercial Skills in the Next 18 Months ft. Jon Johnson (Gainsight)

Customer success is changing fast, and the CSMs who thrive will be the ones who speak the language of revenue. In this episode of Unchurned, Josh Schachter sits down in New York with Jon Johnson, former co-host of [Un]churned & Strategic Principal Customer Success Manager at Gainsight, who manages some of the largest global accounts in the industry. Jon shares how he keeps multinational stakeholders aligned, why empathy still matters at the executive level, and why he thinks CSMs need to take ownership of commercial outcomes before the job forces the issue. They also debate whether SaaS will go “headless” in the next 18 months and how AI has changed Jon’s workload and anxiety. The conversation ends with Jon reading from his poetry collection Caterwaul and a lightning round. Timestamps 0:00 - Preview & Intro 0:57 - Jon Johnson returns to [Un]churned & the banter 2:35 - What Jon does at Gainsight 4:55 - Practising empathy and making customers feel valued 9:00 - Josh makes a surprise announcement 9:51 - 15 years in CS: from startups to global enterprise 11:00 - How customer success changes when you're managing thousands of users 13:00 - Why CSMs are moving closer to the executive level 16:30 - The three pillars: commercial, strategic, technical 18:38 - Why CSMs need commercial accountability 23:23 - Will B2B SaaS become headless in the next 18 months? 27:21 - AI, anxiety, and staying proactive 31:42 - Caterwaul: turning anxiety into art 34:28 - Jon reads “Holy Hands” 36:00 - Deconstructing faith and holiness 38:30 - Lightning round What You'll Learn - How AI is pushing CSMs toward more strategic, executive-level work - Why being proactive about AI reduces AI anxiety - Why CSMs should build commercial skills now, before they’re forced to - How to reframe “value” so CSMs can tell the story of their impact - Why enterprise SaaS adoption will move differently from SMB and mid-market - How consumption and outcome-based pricing can give CS a real seat at the table - Whether SaaS will really go headless, and what that means for CS teams --- Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com --- Where to Find the Guest Jon Johnson: https://www.linkedin.com/in/jonwilliamjohnson/ Jon's Music - Wild Coast: https://open.spotify.com/artist/17TwPEUjOWx4BESKVsqrPK?si=8DjlJdq0SWePHS5r-v1FGQ Jon on Substack: https://jonwilliamjohnson.com/ --- Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/ Unchurned Substack: https://unchurned.substack.com/

October 21, 2026Episode 21538 min

Is Your AI Paying Off? Your CFO Wants Proof ft. Rod Cherkas (HelloCCO)

Is AI still an experiment on your customer success team, or is it delivering results? In this episode of Unchurned, Rod Cherkas, CEO of HelloCCO and author of The Chief Customer Officer Playbook for the AI Era, joins Josh Schachter to talk about what post-sale leaders need to do now. Rod shares findings from his research with nearly 200 post-sale leaders, explains why CFOs are asking for proof of AI's impact, and gives a practical path from scattered pilots to measurable results. The conversation covers governance, change management, and the leadership habits that make AI stick, along with a real example of AI automating a painful handoff process. If you're planning for 2027, this episode gives you a clear way to think about it. What you'll learn - How to connect AI initiatives to the metrics your CFO cares about - Why leader adoption matters more than tool rollouts, and how to model AI use for your team - How to pick 4–5 key metrics and align AI pilots around one or two of them - A simple way to start with a company-grounded AI assistant, without overbuilding the knowledge base - When to buy enterprise AI tools and when (and when not) to build on top of them - How to assign an AI champion on your team and create a practical rollout structure - What the future of customer success roles may look like, and which skills will matter most Timestamps 0:00 - Preview 1:10 - Introduction & Meet Rod Cherkas 3:15 - Why CFOs want measurable AI results 5:20 - Rolling out AI with governance and expectations 6:28 - Why leaders are resisting change 10:20 - Lessons from his time at Marketo for the AI era 12:38 - Frontline innovators who are ahead of the curve 13:45 - Focusing on continous L & D 15:10 - Automating the sales handoff 17:30 - Starting simple with a company-grounded AI assistant 20:10 - Measuring AI impact with key metrics 22:28 - Why change management takes longer than expected 23:37 - Delegating AI vs. leading it yourself 27:35 - Role modeling and making AI part of daily work 30:15 - Build vs. buy: what to build and what to avoid 33:35 - The future of customer success --- Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com --- Where to Find the Guest Rod Cherkas: https://www.linkedin.com/in/rodcherkas/ --- Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/ Unchurned Substack: https://unchurned.substack.com/

October 17, 2026Episode 18739 min

How Salesforce Cut Customer Attrition From 20% to 8% ft. Michael Marguglio

Most companies treat renewals as a sales function. The real shift is treating retention as a job for the whole company. In this episode of the [Un]Churned Podcast, Josh Schachter sits down with Mike Marguglio, EVP of Global Renewals at Salesforce, to unpack how his team manages almost 400,000 renewals a year, how Salesforce brought attrition from over 20% to about 8%, and what AI agents are actually doing in renewals today. Mike shares how a renewals agent turned hours of contract research into an executive view, what hasn’t worked with AI, and how the shift from licenses to consumption is changing the renewal playbook. They also dive into: - How the attrition council aligns senior leaders across the company on retention - Why “a dollar of existing business is just as important as a dollar new business” - How a renewals agent, Ask Renewals, and a long-tail agent are changing the job - What hasn’t worked with AI: incomplete summaries, distrust, and low adoption - How pricing is shifting from licenses to consumption and human-plus-agent models - Why Mike wants renewal to be “a non-event” If you’re leading renewals, building a customer success team, or trying to figure out how AI agents fit into retention, this episode shows how Salesforce runs renewals at scale. Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com . Chapters 00:00 – Intro & Salesforce Renewals at Scale 01:36 – Why 400,000 Renewals Is So Complex 05:03 – The Attrition Council: From Over 20% to About 8% 09:42 – What the Renewals Team Is Doing With AI 17:09 – What AI Caught That Humans Missed 20:28 – How Pricing Changes the Renewal Playbook 22:06 – What Hasn’t Worked With AI 26:05 – AI Adoption and the One-Year Forecast 29:00 – Automating the Long Tail 35:27 – Advice for People Starting Out in Renewals Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com Where to Find the Guest: Mike’s LinkedIn: https://www.linkedin.com/in/michael-marguglio-209895/ Where to Find the Host: Josh’s LinkedIn: https://www.linkedin.com/in/jschachter/ Unchurned Substack: https://unchurned.substack.com

October 7, 2026Episode 21326 min

"We Will Die": Why QuotaPath Is Betting Everything on AI-Native Services ft. AJ Bruno (QuotaPath)

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com . Can a nine-year-old SaaS company reinvent itself as an AI-native services business before the market leaves it behind? On this episode of Unchurned, Josh Schachter, SVP of Strategy and Go-to-Market Development at Gainsight, sits down with AJ Bruno, Co-Founder and CEO of QuotaPath. AJ started QuotaPath after years of reps asking why they couldn't get paid correctly. Today the company serves more than 1,000 customers and over 50,000 reps. Now it's making its biggest bet yet: running commissions for customers instead of selling them software seats, and eventually pricing on outcomes like improved GRR and lower cost of sale. AJ and Josh compare notes on how Gainsight and QuotaPath are both moving to AI-native services. They discuss why trust is the real barrier, how to prove causality when many factors drive revenue, why buyers resist outcome-based pricing, and what it's like to build a startup inside your own startup while still hitting plan for the board. AJ is candid about the stakes: if QuotaPath doesn't make this move, it becomes another forgotten SaaS tool. --- What You'll Learn - Why so many companies deliberately keep comp plans confusing, and what that costs them - Why product-led growth failed for a sensitive category like commissions - How QuotaPath is moving from seat-based SaaS to AI-native services - What "selling outcomes" actually means, and how incentives can move metrics like GRR - Why outcome-based pricing is a hard sell, and how a crawl-walk-run approach reduces risk - How Gainsight is applying the same model to end-to-end renewals - What it takes to rediscover product-market fit inside a mature company --- Timestamps 0:00 - Preview & Meet AJ Bruno 3:35 - What is QuotaPath? The compensation & commissions problem 5:15 - Why companies keep comp plans confusing 6:20 - Why product-led growth didn't work for comp 8:20 - 10 years in: founder envy and wild pivots 10:34 - The return of hustle culture and in-office startups 13:00 - The pivot: from SaaS seats to AI-native services 16:48 - Selling outcomes: incentives that move GRR 19:19 - What QuotaPath actually runs for customers 21:53 - Why nobody wants to pay for outcomes 23:20 - Building a startup within a startup 25:15 - AI-native services unite --- Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com --- Where to Find the Guest AJ Bruno: https://www.linkedin.com/in/ajbruno3/ --- Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/ Unchurned Substack: https://unchurned.substack.com/

September 30, 2026Episode 21234 min

Can AI Really Manage Your Entire Renewal Book? ft. Grant Clarke (Gainsight))

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com . The future of customer renewals is here. And it's AI-native. Josh Schachter sits down with Grant Clarke, EVP & GM of Gainsight Atlas, to explore how AI agents combined with human renewal managers are transforming the renewal landscape. Grant, a 15-year veteran of renewal operations at ServiceSource, explains how Atlas manages entire renewal books through an outcome-based model—not software licensing. Discover why deploying AI agents in renewals is harder than it looks, how Gainsight is pioneering a new category called AI Native Services (AINS), and why the long tail of customers just became manageable. Plus: the surprising story behind Grant's 15 beehives outside Nashville. --- What You'll Learn - How AI agents are transforming customer renewals at scale - Why deploying AI agents in renewals is fundamentally hard - The margin economics that make productizing AI agents profitable - Why the long tail of customers is now economically viable to serve - How combining AI + human renewal managers creates better customer outcomes --- Timestamps 0:00 - Preview & Meet Grant Clarke 2:00 - What is Atlas? 4:50 - Grant's Background: ServiceSource & Dropbox 11:05 - How Atlas onboards a new customer 13:04 - Data hygiene: "The D word" 14:21 - The ideal customer profile for Atlas 16:20 A day in the life: the Atlas cockpit 17:55 - When the agent hands off to a human 19:05 - The learning loop: forward deployed engineers & 2-week sprints 20:10 - The business model: avoiding the pure-services trap 22:04 - Mirage PMF: go fast, go slow, go fast again 23:35 - What's next for Atlas: Agentic judgment and renewal edge cases 26:40 - Can AINS hit 70% gross margins? 26:35 The renewal action inventory: 10–25 actions per renewal 28:38 From 20% to 55% agent-led actions: margin accretion 29:43 Grant's 15 beehives outside Nashville 32:39 Wrap-up --- Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com --- Where to Find the Guest Grant Clarke: https://www.linkedin.com/in/grantclarke/ --- Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/ Unchurned Substack: https://unchurned.substack.com/

September 23, 2026Episode 21141 min

Notion's Outcomes Architects on Why Today's CSMs Are Builders

Most companies think of customer success as a support function that ships software. The real shift is treating it as a co-build practice that ships outcomes. In this episode of the [Un]Churned Podcast, Josh Schachter sits down with Christina Parra, Ariel Risman, and Kellie Woodin, three members of Notion's Outcomes Architecture team, to unpack how Notion rebuilt its entire customer success motion around AI, workshops, and shared commercial ownership. Christina, Ariel, and Kellie share how their roles evolved from traditional CSM to "Outcomes Architect," why they stopped selling software and started selling work, and how an AI maturity model now shapes everything from onboarding workshops to renewal conversations. They also dive into: The shift from customer success manager to outcomes architect and what it actually means to "co-build" with a customer How workshops (some with 180+ attendees) replace one-to-many trainings Proving ROI in a consumption-based pricing model, credit by credit Why CS teams are absorbing commercial ownership and what that's taught them about creative expansion levers Notion's internal multi-agent feature-request pipeline, and why they see AI as abundance, not scarcity If you're rethinking what customer success looks like in an agentic AI world, or figuring out how to prove ROI on usage-based pricing, this episode is a blueprint for turning your CS team into co-build architects. Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com . Chapters 00:00 – Intro & Guest Backgrounds 01:36 – What Is Notion? 04:25 – From Customer Success to Outcomes Architecture 08:51 – Ariel's Book: Deep Discovery & the Workshop Format 15:10 – The AI Maturity Model 21:37 – From Success Plans to AI Transformation Plans 23:14 – Benchmarking, ROI & Proving Value in Consumption-Based Pricing 28:01 – Becoming Strategic Partners: CS Owns Commercials 32:50 – Lessons From Owning Renewals & Hiring for Curiosity 37:30 – The Feature Request Pipeline & AI as Abundance Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com Where to Find the Guests: Christina Parra's LinkedIn: https://www.linkedin.com/in/christina-wills/ Ariel Risman's LinkedIn: https://www.linkedin.com/in/ariel-risman/ Kellie Woodin's LinkedIn: https://www.linkedin.com/in/kelliewoodin/ Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/ [Un]churned Substack: https://unchurned.substack.com

September 16, 2026Episode 21032 min

Owning Retention & Standardizing CS Across 17 Acquisitions ft. Rebecca Nerad (Advantive)

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com . Rebecca Nerad, VP of Customer Success at Advantive, owns retention across four lines of business built from 17 acquisitions in four years. She joins Josh to break down what post-merger integration looks like from the post-sales seat:sitting in on diligence before deals close, inheriting handshake contracts nobody documented, and owning the renewal number for customers she's only just met. Plus the objection-handling agent she built on months of renewal desk recordings, and her candid take on why she still can't measure what it's worth. --- What You'll Learn - How to structure a CS org that spans across multiple lines of business - How to not lose customer knowledge from acquired companies - Hiring & coaching for empathy - The internal objection-handling agent built from renewal negotiation history - Why time to response may be the retention metric AI actually moves - The customization trap AI reintroduces --- Timestamps 0:00 - Preview & Intro 0:58 - Meet Rebecca Nerad (VP of CS, Advantive) 1:22 - 17 acquisitions in four years 3:52 - Playbook for post-merger customer success 5:12 - Handshake deals and undocumented contracts 6:51 - What acquired companies do better 7:46 - Running CS post-sales motion 11:15 - Staffing CSMs by industry, not product 13:41 - Hiring for curiosity and EQ 14:28 - How you actually coach empathy 17:48 - Taking an agentic AI course as a VP 18:55 - Building an objection-handling agent 22:05 - The AI measurement problem 24:00 - Time to response as the real lever 25:32 - At-risk tickets, save plays, and QBRs 28:24 - Grading the long-tail segment 29:19 - AI adoption as the CS opportunity 30:23 - The dashboard-at-scale trap --- Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com --- Where to Find the Guest Rebecca Nerad (Advantive): https://www.linkedin.com/in/rebeccanerad --- Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/ Unchurned Substack: https://unchurned.substack.com/

September 9, 2026Episode 20931 min

Stop Asking "Would You Renew?" Ask This Instead ft. Bob London

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com . Most CS and sales teams have been told to "be more strategic." Few have been shown how. Josh Schachter talks with customer discovery expert Bob London about what it actually takes to move a team above the line. Bob gets tactical fast: the inverted-pyramid structure that works for a 30-minute discovery call or a 5-minute QBR opener, the setup and board-level question that disarms and differentiates in the first few minutes, and the competitor question that CS leaders tell him is the best churn-risk signal they have. He's also honest about the hard part. Methodologies don't adopt themselves, the ROI case rests on catching a handful of surprise churns, and behavior change only shows up if you track it: one-on-ones, keyword tracking, and AI scoring of real call transcripts before and after. --- What You'll Learn - Why "be more strategic" is a directive without a path, and what to say to your team instead - How to structure a conversation as an inverted pyramid - Why "if your renewal were tomorrow, would you renew?" puts customers on the spot and gets you nothing - The "head turner" follow-up that surfaces the gap between what customers have and what they're curious about - How to spot the trigger words that make a question feel like it's about the customer's world - What leaders have to do after the workshop for any of it to take hold - A realistic way to think about ROI when the outcome is prevented surprise churn - How AI call scoring can measure conversation quality before and after training --- Timestamps 0:00 - Preview & Intro 1:48 - Meet Bob London 2:28 - Why "be more strategic" is pressure with no path 5:18 - The mindset shift leaders have to make first 7:45 - The inverted pyramid and the board question that changes the conversation 14:52 - Forget "would you renew?" (ask this instead) 20:25 - Why customer-world trigger words work 22:18 - The board bullet point question 23:00 - How to measure ROI on better conversations 27:11 - Bob's path from fired CMO to 3,000 interviews --- Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com --- Where to Find the Guest Bob London : https://www.linkedin.com/in/boblondon/ Website: https://www.boblondon.co/ --- Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/ Unchurned Substack: https://unchurned.substack.com/

September 2, 2026Episode 20743 min

80% of VP Roles Are Never Posted. Here's How to Find Them ft. Andy Mowat (Whispered)

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com . The best executive roles are never posted, so how do you find them? Andy Mowat, founder & CEO of Whispered and former exec at four unicorns, joins Josh Schachter to pull back the curtain on how senior go-to-market and CS leaders actually land their next role. After navigating between operating roles and founding companies himself, Andy built Whispered so top executives could share unposted roles and interview intel instead of competing in the dark. In this conversation, he shares the playbook. Whether you're quietly looking while in seat or actively on the market, this episode is a masterclass for job hunt. --- What You'll Learn - Why 80%+ of VP and C-level roles are never posted publicly - How VC/PE talent partners differ from executive recruiters, and how to get on their radar - Why you should build relationships with people who already have the job you want - Why role specificity beats being "open to any job" - How to use target lists to unlock loose connections in your network - Why backdooring to mid-level employees works (you don't need the hiring manager) - How to treat your job search like an outbound sales funnel - When comp and role level are actually negotiable - Why thank-you notes still matter more than you think - What's happening in the CS hiring market - Why AI-native companies are heading into a churn wave --- Timestamps 0:00 - Preview & Intro 1:28 - Meet Andy Mowat (Founder, Whispered) 5:28 - How A+ candidates search differently 6:52 - Talent partners vs. recruiters and the 340-person Google group 10:15 - Career clarity, target lists & the power of loose connections 15:20 - Find & connect with the people who have the job you want 16:36 - Timing, recency bias, and building real relationships 18:50 - Why senior roles are never posted publicly 22:44 - Monitoring unposted roles with scrapers and AI 23:43 - Why the front door doesn't work 25:40 - No more referral fees 27:53 - Treat your job search like an outbound sales funnel 30:25 - Write thank-you notes 31:31 - The CS job market and the coming AI churn wave 33:03 - Comp negotiation and why half of all comp numbers are flexible 34:45 - Can you level up in this market? --- Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com --- Where to Find the Guest Andy Mowat (Whispered): https://www.linkedin.com/in/amowat/ Whispered: https://www.whispered.com/ --- Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/ Unchurned Substack: https://unchurned.substack.com/