[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/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

Alexis Hennessy, a Partner at Heidrick & Struggles and co-founder of their post-sales executive search practice, shares her insights on the evolving role of the Chief Customer Officer. She highlights the necessity of retention, explaining why hiring for CCOs is on the rise again. Alexis emphasizes the importance of listening in the first year and adapting strategies accordingly. The conversation also touches on the traits that successful CCOs possess and the increasing relevance of AI in customer retention strategies, suggesting a promising future for the role.

In this enlightening discussion, Erica Kuhl, EVP at Gainsight and a key architect behind Salesforce's massive customer community, shares her journey from early employee to community innovator. She reveals how she built a peer-driven forum with limited resources, emphasizing community as a vital retention strategy. Erica discusses the significance of creating a unified Digital Customer Success experience and provides actionable insights on pitching community initiatives to boost retention by four times. Prepare to be inspired by her scrappy approach to customer engagement!

Colin Slade, Senior VP of AI Strategy and Customer Success at Cloudbeds, led a nimble team that transformed a struggling post-sales operation into an AI-powered powerhouse. They developed over 150 workflows in just nine months, automating 75% of repetitive tasks and saving 7,000 hours monthly. Colin discusses the initial fears of job loss among staff, the stepwise approach for AI adoption, and the importance of team structure. He emphasizes the impact of embracing constraints for innovation and fostering a culture of fearless experimentation.

Cat Valverde, founder of the Enterprise AI Group, specializes in helping organizations adopt AI effectively. She discusses the common pitfalls of enterprise AI projects and reveals her groundbreaking 15-Minute Rule for enhancing adoption rates. By focusing on human-centered approaches, she outlines a simple four-week framework to engage users and boost buy-in. The conversation highlights the importance of reducing cognitive load, using psychological insights, and leveraging social proof to achieve remarkable increases in AI adoption.

Mark Roberge, co-founder of Stage 2 Capital and former HubSpot CRO, dives into the transformative power of AI in sales and market strategies. He emphasizes the need to replace CAC obsession with a focus on optimizing customer lifetime value. Roberge outlines four phases of AI evolution in go-to-market tactics, predicting blurred departmental lines and the rise of autonomous agents. He also discusses the societal implications of AI, questioning whether capitalism can adapt alongside these advancements. It's a captivating look at the future of work and customer dynamics!

Jacob Bank, the founder and CEO of Relay.app and a former Google product leader, dives deep into the world of AI agents. With over 14 years of experience, he discusses how agents will soon handle nearly all tasks on computers. Jacob distinguishes between workflows and agents, stressing the importance of context over complex prompts. He highlights why small businesses adopt AI faster than larger enterprises and predicts that everyone will need to become an agent manager, focusing on training and supervising these digital teammates.

Omer Rabin, a General Partner at TLA Ventures and former Gainsight chief evangelist, teams up with Chad Horenfeldt, VP of Customer Success at Siena AI and author of The Strategic CSM. They discuss the meteoric rise of customer success from a fledgling idea to a billion-dollar industry. Omer shares his belief that the next wave of CEOs will likely emerge from customer success roles. They emphasize the transformative power of AI in regaining strategic focus and highlight the importance of aligning customer success metrics with organizational goals.

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/

Customer success leaders share how they're handling massive renewal volumes, with Rockwell Automation managing over 100,000 renewals. They highlight the shift from time-based outreach to AI-driven engagement signals. Fleetio discusses using AI to automate CSM tasks, allowing them to focus on strategic advisory roles. Insights on effective change management and AI's role in analyzing customer feedback reveal essential strategies for driving retention and efficiency. The conversation also covers the importance of integrating data from various systems to enhance overall customer health.