Josh Schachter - UpdateAI
Unchurned - The No. 1 podcast for Customer Success
The Unchurned podcast brings you the stories that will help you forge incredible customer relationships, prevent churn, & build institutional knowledge. The CS & BS series is a part of the Unchurned podcast wherein, with each episode, our hosts - Kristi Faltorusso, Jon Johnson, Josh Schachter, and special guests uncover the secrets of top leaders and innovators of companies so that you can advance your career and the performance of your customer success team. Unchurned, and the CS&BS series, are presented by UpdateAI - https://update.ai/
Author
Josh Schachter - UpdateAI
Category
Podcast website
Latest episode
Jul 8, 2026
Where to listen?
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Episodes
How We Turn Churn Into Comebacks (The Revenue Hiding Inside Your Churn) ft. Eleanora White (Supermetrics) 27.02.2026 15:48
Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned Is the future CSM a generalist empowered by specialist AI agents? Live from Pulse Europe, Eleanora White, Global Head of CS & Solutions Architects at Supermetrics, joins Jenny Calvert to break down how her team is operationalizing Agentic AI inside customer success. From...
B2B Communities Aren't Dead, Your Outdated Metrics Are ft.Jon Wishart & Brian Oblinger 25.02.2026 37:53
Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned Is community in B2B SaaS a cost center — or a growth engine hiding in plain sight? In this episode of Unchurned, Josh Schachter sits down with Jon Wishart and community strategist Brian Oblinger to break down what community really means beyond vanity metrics and buzzwords. T...
75% of SaaS Companies Will Disappear ft. Brett Queener (Bonfire Ventures) 20.02.2026 16:03
Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned 18 months ago, venture capitalist Brett Queener made a bold prediction: 75% of customer-facing software companies would disappear. Now he’s back—with receipts. On this episode of Unchurned, Brett explains why traditional SaaS moats have collapsed, why “system of record” is n...
What Consumption-Based CS Looks Like Inside a $100B Company ft. Jared Collins (Dell) 18.02.2026 24:47
Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned What happens when you bring consumption-based customer success into a company? In this episode of Unchurned, Jared Collins, Senior Director of Customer Success at Dell Technologies, shares how the Apex team is building a modern CS engine inside a $100B infrastructure giant....
A Masterclass in Category Creation from the Leaders at Gong and Gainsight ft. Udi Ledergor (Gong) & Lauren Olerich (Gainsight) 11.02.2026 48:51
Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned Udi Ledergor joined Gong as employee #13 and marketer #1, helping build it from a 12-person startup to a category-defining revenue intelligence leader. As Chief Evangelist and author of "Courageous Marketing," he's learned one hard truth: if you don't have product-market-fit...
How Do You Measure AI Proficiency in Your CS Team? ft. Guy Galon (Obrela) 06.02.2026 15:31
Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned Guy Galon, CCO at Obrela, joins Jenny Calvert at Pulse Europe in Dublin to discuss how he's transforming CS hiring and operations for the AI era. In this conversation, Guy explains how he measures AI capability in his team, why he's building some AI tools internally...
What Happens When You Apply Digital Motions to Your Biggest Accounts? ft. Christine Lavery (Conga) 04.02.2026 34:02
Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned Christine Lavery, VP of Customer Success at Conga, shares why the traditional approach to digital customer success is broken and how she's applying digital motions across all customer tiers—not just the long tail. Christine discusses her two major priorities for 2026: im...
This CCO Won't Ask His Team What He Wouldn't Do Himself (And Why) ft. Jim Richmond (Smartling) 28.01.2026 29:08
Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned Jim Richmond is the Chief Customer Officer at Smartling, an AI-powered translation company doing AI "before it was cool" since 2009. Leading 50 professionals across support, services, and customer success, Jim shares his 2026 playbook: why GRR is his North Star, ho...
Why Your Post-Sales Budget Should Be 7% of Revenue (Not 10%) ft. Abbas Haider Ali (Github) 21.01.2026 55:04
Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned GitHub's SVP of Customer Success Abbas Haider Ali reveals why post-sales investment should drop from 10% to 7% of revenue, breaks down the 6-layer customer health model used by Fortune 100 companies, and introduces the "specialized generalist"—the AI-native CSM role that's r...
18 Months, 7,000 Customers, 67% Support Resolution: Inside Intercom's FDE Strategy ft. Diego Ballona (Intercom) 14.01.2026 29:39
Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned What if the fastest path to product-market fit isn't building more features—it's deploying engineers to solve customer problems? Diego Ballona, Senior Director of Engineering at Intercom, runs Forward Deployed Engineering—a team that helped scale Fin from 5 design partners t...
3 CS Trends That Will Define 2026 & Kristi's Next Chapter ft. Kristi Faltorusso 07.01.2026 30:02
- Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned The customer success landscape is about to shift dramatically. Kristi Faltorusso, fresh off her departure from ClientSuccess after five years, reveals the three trends that will define CS in 2026—and the second one might surprise you. From the explosion of CS Ops to the "E...
How To Stop Managing 38% of Your Customers in 2026 ft. Yvette Hill (F5) 24.12.2025 26:12
Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned Every major transformation Yvette Hill has led started the same way: with a moment of panic. Across a 35-year career at IBM, Xerox, Microsoft, and now F5, Yvette Hill, SVP of Customer Success and Global Renewal Sales at F5, has repeatedly observed the same pattern: big deals...
Why $100M AI Companies Are Failing at Renewals? ft. Cassie Young & Kyle Poyar 17.12.2025 37:30
Ready to churn less and win more? 🏆 Subscribe for a monthly roundup of every episode at gainsight.com/unchurned Two of SaaS's most influential voices just sounded the same alarm: Cassie Young, General Partner at Primary Ventures, and Kyle Poyar, founder of Growth Unhinged, both published viral articles warning of a "gross retention apocalypse" in AI-powered SaaS. Cassie's in...
The #1 Thing Great CCOs Do in Year One ft. Alexis Hennessy (Heidrick & Struggles) 10.12.2025 20:28
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 year...
How Community Increases Retention 4X ft. Erica Kuhl (Gainsight) 19.11.2025 32:13
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. Tha...
How a 5-Person Team Built 150 AI Workflows That Changed an Entire Company ft. Colin Slade (Cloudbeds) 12.11.2025 48:37
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 org...
A Simple Habit That 3x’ed AI Adoption Rates: The 15-Minute Rule ft. Cat Valverde (Enterprise AI Group) 06.11.2025 15:30
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 he...
Why Your Ideal Customer Profile Is Broken and How AI Can Fix It ft. Mark Roberge (Co-Founder of Stage 2 Capital) 05.11.2025 47:32
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-driv...
The Only Agentic AI Guide You'll Ever Need ft. Jacob Bank (Relay.app) 29.10.2025 42:30
The Ex-Google PM Who Spent 14+ Years Building AI Agents ft. Jacob Bank (Relay.app) 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 businesse...
Are CSMs the Next Generation of CEOs? ft. Omer Rabin (TLA Ventures) & Chad Horenfeldt (Siena AI) 22.10.2025 33:14
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” sounde...
From Radio Host to CPO: Why Should You Always Work Backwards from Renewals? ft. Venk Chandran (PathFactory) 15.10.2025 34:12
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...
Inside Pulse: How 7 CS Leaders Are Moving Their Biggest Boulders With AI 08.10.2025 31:36
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...
Is Agentic AI The End of ARR? ft. Brett Queener (Bonfire Ventures) & Chuck Ganapathi (Gainsight) 01.10.2025 51:40
"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...
How BMC's CCO Built AI Agents That Triple Productivity ft. Sofia Barbosa (BMC Software) 24.09.2025 30:34
How Human-Centric AI Frees CSMs for Strategic Work at BMC Leading customer success at a global scale is never easy—especially after a company split. For Sofia Barbosa, this meant steering a leaner team while still supporting hundreds of BMC products worldwide. The challenge: deliver more impact with fewer hands. The solution: build Succedo, an AI platform that reimagined how her team worked. The r...
How to Drive Innovation & Democratize AI as a CS Leader ft. David Karp (Disqo) 17.09.2025 28:02
How Disqo Sparked an AI Movement With a Company-Wide Hackathon When everyone was talking about AI but few knew where to start, Disqo took a bold step: they cleared two full days and ran a company-wide AI hackathon. The result? 70 people, 15 teams, and a wave of innovation that’s still driving value today. In this episode, David Karp, Chief Customer Officer at Disqo, shares the inside story of how...
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