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

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, no amount of marketing genius will save you.In this conversation with Josh Schachter and Lauren Olerich, Udi shares the real indicators of product-market-fit, when companies should actually hire their first marketer, and how Gong evolved through multiple category iterations—from conversation intelligence to their current positioning as an AI operating system for revenue teams.The discussion digs into Gong's "brand as person" exercise that created consistency across everything from content voice to event experiences, why data-driven content about salespeople cursing went viral, and the value of leaving raving fans everywhere you go. Udi's 27-year working relationship with Gong's CEO proves that burning bridges is career suicide in a small industry.For anyone building brands, creating categories, or wondering if their startup is ready for marketing investment, this episode cuts through the fluff with practical frameworks and hard-won lessons.---Do you love great TV? Lauren co-hosts a podcast about popular TV show finales called The Finale Pod. Take a listen on Apple Podcasts, Spotify, or wherever you get your podcasts---Timestamps0:00 - Preview & Introduction0:54 - Meet Udi Ledergor and Lauren Olerich 4:00 - Udi's early journey at Gong7:00 - When should you hire your first marketer? 10:55 - Lauren's early journey at Gainsight14:00 - How Gong created the revenue intelligence category in 201922:58 - Diamond is forever28:10 - Pulse predates Gainsight32:17 - Early struggle at Gainsight33:40 - The importance of domain expertise41:52 - Brand as human: The exercise that creates consistency across everything---What You’ll Learn* Evaluating product-market-fit for marketing to succeed* How to create consistent tone across content, events, and category positioning* Real tactics behind building and evolving categories across 10 years* Why leaving raving fans at every company matters more than titles* How a 27-year working relationship led to employee #13 becoming Chief Evangelist* How data-driven content can go viral while staying perfectly on-brand* When to publish the controversial insights your competitors are too afraid to share---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find Udi LedergorLinkedIn: https://www.linkedin.com/in/udiledergor/Book "Courageous Marketing": https://www.udiledergor.com/bookWhere to Find Lauren OlereichLinkedIn: https://www.linkedin.com/in/laurenolerich/The Finale Pod: Apple Podcasts⁠ | Spotify⁠---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

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 at a cybersecurity company, and his three big bets for AI in 2026. Guy tackles the generalist vs. specialist debate, explains why his technical background as a software engineer helped him earn credibility as a CS leader, and explores the emerging question: What does it mean to manage AI agents? From performance reviews for bots to getting CS leaders a real seat at the revenue forecasting table, this conversation covers the practical and philosophical challenges of leading customer success in 2026.---Timestamps0:00 - Preview & Introduction0:54 - Meet Guy Galon, CCO at Obrela2:27 - The Generalist vs. Specialist Debate in the Age of AI3:35 - The Multifaceted CSM Framework: Origins and Evolution4:47 - How to Measure AI Proficiency6:05 - 2026 AI Strategy8:03 - What Changes When AI Delivers on These Three Promises9:41 - Q4 Advice: Think in 8-10 Weeks, Not 1211:30 - Getting CS a Seat at the Revenue Forecasting Table13:00 - The Human Element AI Can't Replace: Trust and Influence14:14 - The Future of Managing AI Agents---What You’ll Learn* How the Multifaceted CSM Framework helps identify talent across five key capability areas* How to balance AI innovation with data compliance in highly regulated industries like cybersecurity* How to move CS from execution-focused roles to strategic contributors in revenue forecasting* The difference between building internal AI capabilities vs. using external tools in customer success* What it might look like to manage AI agents in the future (priorities, objectives, performance reviews)---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find Guy GalonLinkedIn: https://www.linkedin.com/in/guy-galon-b1a80/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

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: implementing product analytics as the foundation for customer outcomes and rolling out SMART goals to move from vague value conversations to measurable impact. She also explores how AI is transforming customer intelligence by synthesizing structured data (product analytics) with unstructured data (emails, support tickets, NPS verbatims) to create a complete picture of customer health.---Timestamps0:00 - Preview & Introduction1:25 - Meet Christine Lavery2:15 - Overview of Conga3:05 - Conga's acquisition of PROS and the future of CPQ4:04 - Structure of Christine's 100-person global CS organization6:35 - Why digital motions shouldn't be "long tail only."9:52 - Mapping customer journeys and communication strategies13:42 - Collaboration between CS, Product, and Marketing19:42 - Reporting to revenue and driving growth25:30 - Breaking down the SMART goals framework for customer outcomes27:42 - How AI fits into product analytics and customer intelligence31:27 - Why CS leaders must fight for a seat at the table---What You’ll Learn* Why limiting digital customer success motions to only "long tail" customers is a mistake * How to scale one-to-many strategies across enterprise and strategic accounts* How to use SMART goals to transform vague "value" conversations into measurable customer outcomes that clearly demonstrate ROI* The difference between basic product analytics and sophisticated use-case tracking that helps you coach customers to better outcomes* How AI synthesizes structured data (product usage) and unstructured data (emails, support tickets, NPS) to create a complete picture of customer health* Why CS leaders must actively fight for a seat at the executive table---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find Christine LaveryLinkedIn: https://www.linkedin.com/in/christine-lavery/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurnedJim 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, how he's building systems to scale 4x, and why role specialization beats generalization in the AI era.Jim reveals how AI bots eliminated single-touch support tickets at Smartling, why he still carries his own book of business as a CCO, and his career advice for aspiring leaders to build the professional empathy that makes them an authentic partner.---Timestamps0:00 - Preview & Introduction1:25 - Meet Jim Richmond 1:50 - Smartling Overview4:33 - 2026 Priorities: GRR as the North Star metric6:30 - Building a four-quarter forecast9:40 - Building systems for 4x growth12:24 - Forecasting to eliminate surprises14:55 - Will AI make CSMs more generalized or specialized?18:32 - How AI bots eliminated single-touch support tickets21:42 - What it's like being a first-time Chief Customer Officer23:38 - The rule of thirds: How a CCO allocates time25:10 - Why this CCO still carries his own book of business25:52 - Seek out a diversity of experiences---What You’ll Learn* How to build a four-quarter forecast that eliminates revenue surprises* Why role specialization creates more operational leverage than generalization* How AI bots eliminated single-touch support tickets at Smartling* Why leading from the front means carrying your own book of business* How to build professional empathy by seeking diverse experiences across sales, CS, and services---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find Jim Richmond LinkedIn: https://www.linkedin.com/in/jimrichmondatl/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurnedGitHub'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 redefining customer success in 2026. Learn the frameworks CS leaders need to prove ROI, restructure teams, and solve the 80-20 problem in AI adoption.From playbook evolution to knowledge management, this conversation offers a practical roadmap for CS leaders navigating rapid technological change while proving ROI to increasingly demanding CFOs. Whether you're structuring your CS organization, defending your budget, or preparing your team for AI transformation, this episode delivers the frameworks and benchmarks you need.---Timestamps0:00 - Preview & Introduction2:05 - Meet Abbas Haider Ali & GitHub's Scale 3:40 - The 500-Pound Zoom Background Story 8:40 - The Customer Hierarchy of Needs Framework 17:50 - Why CS Playbooks Must Constantly Evolve 21:00 - How Abbas Discovered the CS Budget Benchmark (Surveying 100+ Companies on Post-Sales Investment)25:50 - The Journey from 10% to 7%: AI's Impact on Post-Sales Economics 27:40 - Should You Aim for 7% or 10%? 28:58 - CFO Reactions & Proving ROI in a Post-ZIRP World 33:33 - Under-Investing vs. Over-Investing in Support38:05 - Return on the 10% - 7% Investment46:46 - Introducing the "Specialized Generalist" CSM Role 51:27 - Why AI-Native Organizations Scale Faster 53:00 - Abbas's 2026 CS Resolution---What You’ll Learn* Why post-sales investment should be 7% of revenue and how AI is driving this shift* The ROI framework CS leaders need to defend their budgets to CFOs in a capital-constrained environment* Why customer health models need constant evolution (not static playbooks)* Why specialist roles will move up the value chain in AI-powered organizations* The T-chart model for CSM skills with AI proficiency as the critical vertical capability* Why CS leaders should come from multidisciplinary backgrounds (product, engineering, sales)---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find Abbas Haider Ali: LinkedIn: https://www.linkedin.com/in/abbashaiderali/---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/---Resources Mentioned: - CS operating model- ROI of Customer Success (original)- ROI of Customer Success (updated)- Rise of the Specialized Generalist- The future of CSMs is more generalized

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurnedWhat 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 to 7,000 customers, hitting a 67% resolution rate in 18 months. But FDE isn't professional services rebranded. It's product managers, engineers, and data scientists working directly with customers to accelerate outcomes and turn real friction into features everyone can use.Diego breaks down the exact team structure that makes this work, why outcome-based pricing changes go-to-market strategy, and how to know if FDE is right for your business. If you're scaling an AI product or rethinking how engineering and CS collaborate, this conversation delivers the blueprint.---Timestamps0:00 - Preview & Introduction3:00 - Diego's origin story at Intercom and how FDE emerged organically5:35 - Intercom's scale: 7,000 Fin customers, 67% average resolution rate across all segments7:25 - From 5 design partners to proving the FDE model9:12 - Building the business case and getting leadership buy-in12:05 - FDE team structure18:55 - How FDE turns customer insights into product features23:15 - Ownership boundaries: CSMs vs. FDE teams 25:25 - Outcome-based pricing and why it aligns incentives perfectly27:00 - Diego's golden nugget: Stay open-minded ---What You’ll Learn* How Intercom scaled from 5 design partners to 7,000 Fin customers in 18 months using Forward Deployed Engineering* Why the FDE team structure requires three specific roles working together* How outcome-based pricing changes everything about go-to-market incentives, comp plans, and team alignment* Why FDE engineers need different skills from product engineers* How to know if FDE is right for your business (and why it might not be)* The ownership boundaries between FDE teams and CSMs that make cross-functional collaboration actually work---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find Diego:LinkedIn: https://www.linkedin.com/in/dballona/Intercom: https://www.intercom.comFin AI Agent: https://www.intercom.com/fin---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

- Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurnedThe 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 "ERR apocalypse" hitting tech stacks across the industry, Kristi breaks down what's coming and how to prepare. Plus, she shares the uncomfortable truth about why she left a job she loved and how an hour a day of AI learning built four products in 2025.---Timestamps0:00 - Preview & Introduction1:23 - Kristi is back! 2:34 - Why Kristi Left a Perfect Job?5:20 - What She'll Miss Most6:50 - Building Unbreakable Trust with Leadership9:20 - Kristi's Next Chapter10:35 - Kristi's 2026 Predictions for CS13:13 - The ERR Apocalypse & The Consolidation Wave 15:45 - The Rebranding of CS Ops Roles18:15 - Kristi's Vibe Coding Journey 21:30 - Make AI Learning Fun25:00 - Find and Champion Your AI Champions26:10 - Device Addiction & Reading for Fun---What You’ll Learn* Why companies have been accumulating AI tools and what triggers the consolidation* How CS Ops will become critical as AI and automation require system builders* How to identify and champion the AI early adopters in your organization* The trust formula that built an unbreakable 5-year executive partnership* What the "ERR apocalypse" means for your tech stack ---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find Kristi:LinkedIn: https://www.linkedin.com/in/kristifaltorusso/Website: https://www.kristifaltorusso.com/Newsletter: https://www.kristifaltorusso.com/the-journey-cs-newsletter---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/---Referenced Episodes: - https://www.gainsight.com/episode/why-100m-ai-companies-are-failing-at-renewals-ft-cassie-young-kyle-poyar/- https://www.gainsight.com/episode/how-to-scale-customer-success-with-ai-agents-ft-leeron-yahalomi-aligned/Resources:- ChatGPT: https://chat.openai.com/- Claude: https://claude.ai/- Gamma: https://gamma.app/- Zapier: https://zapier.com/- Replit: https://replit.com/- Lovable: https://lovable.dev/

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurnedEvery 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 on paper, but little customer value realized. Each time, the fix was clear: transform the teams closest to customers into engines for value.Recorded live at Pulse Europe in Dublin, Yvette joins host Jenny Calvert to share why today’s AI shift is the most exciting transformation she’s seen—and how she’s acting on it. From recruiting data scientists into CSM roles to allocating 100% of her budget to AI, tracking 175 customer signals, and forcing automation conversations, Yvette is focused on what works now.This episode is a candid look at leading real change—and why teams that get curious today will pull ahead fast.---Timestamps0:00 - Preview & Introduction[00:00] Introduction: Live from Pulse Europe in Dublin [01:15] Yvette's unconventional path into customer success [02:45] The Xerox transformation: From selling devices to driving outcomes [05:30] Microsoft Azure: Solving the "big commits, no revenue" problem [07:20] Joining F5: Hardware to SaaS, single product to multi-product [09:00] The agentic era: Why AI is the biggest transformation yet [11:45] 100% budget allocation to AI—zero new headcount [13:30] Hiring data scientists as CSMs: The breakfast table story [16:00] Building curiosity in legacy teams: "Be more curious every day" [18:15] Structuring teams for AI: Leaders, data analysts, and business-side AI builders [20:30] Use case #1: Harvesting unstructured feedback across silos [23:00] Holding product teams accountable with ROI-driven insights [25:45] Use case private channel: Aggregating 175 customer engagement signals [28:00] Why you can't wait for IT—and why speed matters more than perfection [30:30] Investing in people: Skills for operating alongside AI agents [33:15] Getting team buy-in: From fear to excitement about AI [36:00] The democratization of AI: Small wins and Titanic shifts [38:45] Final advice: Just get started—the tough stuff isn't harder than the easy stuff [41:00] Closing thoughts: This is CS's time---What You’ll Learn* How to shift from retention-only to expansion-driven CS in a multi-product business* Why Yvette is hiring data scientists as CSMs (and what they bring to the team)* The 175 customer engagement signals F5 is aggregating to predict retention and expansion* How to hold product teams accountable for customer feedback using ROI-driven insights* Why investing in people—not just tools—is the key to AI adoption* The breakfast conversation that changed F5's entire hiring strategy for AI* The ROI framework that holds product teams accountable for customer feedback* Why waiting for the perfect use case means you'll never start---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.---Where to Find Yvette HillLinkedIn: https://www.linkedin.com/in/yvette-hill-smith-0374265/---Where to Find Jenny:LinkedIn: https://www.linkedin.com/in/jennycalvert/

Ready to churn less and win more? 🏆 Subscribe for a monthly roundup of every episode at ⁠⁠gainsight.com/unchurned⁠⁠Two 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 investigation revealed a shocking truth: when she called customer logos cited in AI fundraising decks, nine out of ten had already stopped using the product. Kyle's data showed founders bragging about hitting $10M ARR in a month with zero cohorts up for renewal.In this conversation, they unpack why explosive growth often masks catastrophic churn, distinguishing between Annual Recurring Revenue and what Cassie calls "Experimental Recurring Revenue" - revenue that evaporates when customers realize the product doesn't deliver.The discussion moves beyond diagnosis into what actually works. Kyle introduces forward-deployed engineering as a sales motion—getting customers live in production before they pay prevents churn better than any post-sales fix. Cassie argues we're entering a Customer Success Renaissance where the discipline evolves from reactive firefighting to strategic value delivery.---Timestamps0:00 - Preview & Introduction1:36 - Meet Cassie Young & Kyle Poyar3:00 - The Gross Retention Apocalypse & AI Churn Wave7:25 - ERR vs ARR: The Red Herring - 9 out of 10 Customers Stopped Using10:00 - Series A's Done on "Vibes" 11:05 - What Investors Are Looking For14:40 - The Cluely Controversy: Distribution vs Product Quality16:15 - Why Fast Growth Means Nothing Without Retention Data21:15 - Customer Success as a Core Operating Philosophy29:30 Forward Deployed Engineers as Part of Sales Motion31:40 - Most Overrated Metric 32:08 - Most Underrated Metric33:10 - SaaS Principles That Will Last 10 Years35:30 - The Way Forward---What You’ll Learn* Why 9 out of 10 AI customers cited in fundraising decks have already churned* The critical difference between ARR and ERR (Experimental Recurring Revenue)* The "automatic pass test" top VCs use to evaluate startups in 60 seconds* How to identify your north star usage metric for predicting churn* Why distribution alone isn't enough (lessons from the Cluely phenomenon)* How the Customer Success TAM could 10X if companies focus on the right things---Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at ⁠⁠unchurned.substack.com.⁠---Where to Find Kyle Poyar:LinkedIn: https://www.linkedin.com/in/kyle-poyar/Substack: https://www.growthunhinged.com/Podcast: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102Where to Find Cassie YoungLinkedIn: https://www.linkedin.com/in/cassyoung---Where to Find Josh:LinkedIn: https://www.linkedin.com/in/jschachter/---Resources: Cassie's article: https://topline.beehiiv.com/p/tech-is-on-the-brink-of-a-gross-retention-apocalypse-a-customer-success-renaissanceKyle's article: https://www.growthunhinged.com/p/the-ai-churn-wave

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

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 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)11.4

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/

How Human-Centric AI Frees CSMs for Strategic Work at BMCLeading 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 results spoke for themselves—customer success stories accelerated from months to days, output tripled, escalations dropped, and CSMs finally had time to focus on the strategic work that drives growth.In this episode, Sofia shares the inside story of how she’s embedding AI across customer success at BMC. From value summaries and training path recommendations to support prioritization and statements of work, Sofia is proving that AI isn’t about replacing people—it’s about elevating them. She explains how she manages change, structures her AI teams, and why she believes experimentation (and even failure) is the only way forward.What you’ll learn:- How Succedo helped triple the output of customer success stories.- The role of AI in reducing escalations and improving customer sentiment.- How to build specialized AI teams inside a large enterprise.- Why “human in the loop” remains critical in AI adoption.- The mindset shift leaders need to drive AI transformation.Check out the Key Takeaways & Transcripts: https://www.gainsight.com/presents/series/unchurned/Where to Find Sofia: LinkedIn - https://www.linkedin.com/in/sofiabarbosa/Where to Find Josh: LinkedIn: https://www.linkedin.com/in/jschachter/In this episode, we cover:0:00 – Preview & Introduction1:40 – Meet Sofia Barbosa (CCO, BMC Software)3:15 – Sofia’s promotion and the BMC split6:53 – Why & how Succedo was born11:30 – The impact of using Succedo12:55 – Using AI to create value summaries15:40 – Creating personalized training paths with AI18:35 – AI for support: prioritization and sentiment analysis21:18 – Automating statements of work with AI24:35 – Building “Succedo Forge” and “Succedo Care” teams27:10 – Managing change and team sentiment around AI28:45 – Advice for CCOs driving AI transformationReferenced:- Sofia's post: https://www.linkedin.com/posts/sofiabarbosa_customersuccess-ai-bmc-activity-7366224818586685441-q74P