Retention Is Existential: Gainsight’s New CEO Chuck Ganapathi on RaaS, AI Agents & the 80/20 Trap | Episode 100
Welcome to episode 100! I’m joined by Chuck Ganapathi, Gainsight’s new CEO, for a wide-ranging, candid conversation about where customer success is headed and what leaders should do right now.We start with Chuck’s career through four platform eras: mainframe to client/server to cloud to AI - and how those shifts shape strategy. He shares the little-known origin story of “Customer Success” at Salesforce, Gainsight’s early days, and why integrations (Salesforce, SAP CX, Microsoft Dynamics) are never “done”—they’re living systems that demand clean data and constant tuning.Then we dig into Chuck’s concept of Retention-as-a-Service. In a world where retention is existential, the 80/20 mindset breaks. Every dollar matters, which means every customer matters. We talk agentic AI (augmentation vs autonomy), how a “renewal agent” can cover the long tail, and why the magic is orchestration—letting agents handle the repeatable while humans lean into judgment, relationships, and value.We close with practical automation stories, a few resources Chuck follows, and a reminder that the human-to-human piece isn’t going anywhere.Links in Today's Episode:Ethan Mollik: One Useful ThingSaanya OjhaJamin Ball: Clouded JudgementAndrej Karpathy on the Dwarkesh Podcast: AGI is still a decade away Support the show+++++++++++++++++Like/Subscribe/Review:If you are getting value from the show, please follow/subscribe so that you don't miss an episode and consider leaving us a review. Website:For more information about the show or to get in touch, visit DigitalCustomerSuccess.com. Buy Alex a Cup of Coffee:This show runs exclusively on caffeine - and lots of it. If you like what we're, consider supporting our habit by buying us a cup of coffee: https://bmc.link/dcspThank you for all of your support!The Digital Customer Success Podcast is hosted by Alex Turkovic🎬 This content was edited by Lifetime Value Media.Learn more at: https://www.lifetimevaluemedia.com
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Voice to Value: I Used ChatGPT Voice to Help Build an Automation | Episode 099
In Episode 99, I do something a little different: I take you behind the scenes as I use ChatGPT in voice mode to design a real automation from start to finish. The goal? Build an internal chatbot for product and engineering that’s trained on CX call transcripts stored in Gong, so teams can ask targeted questions (“What’s frustrating customers in Module X?”) and get instant, concise answers with deep links back to the exact call moments.You’ll hear how I frame the problem, push the model to avoid hallucinations, and pick a stack that balances speed, privacy, and scale: Gong → Airtable as the searchable store → a Zapier-hosted chatbot for querying. We also cover transcript hygiene (auto-removing small talk and personal details), vendor privacy considerations, and a simple habit hack: having AI remind you later to actually implement the ideas you generated while walking the dog.I’ll link the step-by-step PDF I asked ChatGPT to generate in the show notes so you can follow along and adapt it to your environment.If this sparks ideas for your own digital CX programs, follow/subscribe and drop a review—it really helps more practitioners find the show.Support the show+++++++++++++++++Like/Subscribe/Review:If you are getting value from the show, please follow/subscribe so that you don't miss an episode and consider leaving us a review. Website:For more information about the show or to get in touch, visit DigitalCustomerSuccess.com. Buy Alex a Cup of Coffee:This show runs exclusively on caffeine - and lots of it. If you like what we're, consider supporting our habit by buying us a cup of coffee: https://bmc.link/dcspThank you for all of your support!The Digital Customer Success Podcast is hosted by Alex Turkovic🎬 This content was edited by Lifetime Value Media.Learn more at: https://www.lifetimevaluemedia.com
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Director vs Doer: Staying Relevant and Thriving in the A.I. Era | Episode 098
In this episode, we dig into a shift I think is non-negotiable in today’s AI-first world: you must become the director, not the doer. Inspired by Dan Martell’s framework, we explore how AI should handle the execution — while you define the outcome, set constraints, and bring the human edge.I introduce the three pillars that separate average from exceptional direction: Vision, Taste & Care. You’ll hear how I use them in real-world workflows, the traps I fell into trying to do everything myself, and a few tactical moves (prompts, boundaries, feedback loops) that helped me step up.If you feel like you’re driving but still stuck doing all the work — this one’s for you.👉 Hit follow/subscribe so you don’t miss future episodes, and if this one lands, leave a review or drop me a line.Support the show+++++++++++++++++Like/Subscribe/Review:If you are getting value from the show, please follow/subscribe so that you don't miss an episode and consider leaving us a review. Website:For more information about the show or to get in touch, visit DigitalCustomerSuccess.com. Buy Alex a Cup of Coffee:This show runs exclusively on caffeine - and lots of it. If you like what we're, consider supporting our habit by buying us a cup of coffee: https://bmc.link/dcspThank you for all of your support!The Digital Customer Success Podcast is hosted by Alex Turkovic🎬 This content was edited by Lifetime Value Media.Learn more at: https://www.lifetimevaluemedia.com
After a short hiatus, Alex is back—and he’s bringing some big energy and even bigger ideas to the Digital Customer Success podcast. In this solo episode, he shares a deeply personal and practical reflection on how we can create magical, human moments in our digital programs—at scale.Inspired by Will Guidara’s book Unreasonable Hospitality, Alex explores what it means to go beyond the expected, whether that’s sending a baby gift, a surprise mouse (the tech kind), or a handwritten note. The kicker? You can use AI and automation to help you spot those moments—without losing the human touch.You’ll learn:Why emotional connection matters more than ever in CXHow to train your systems (and your team) to spot moments of magicReal-world examples you can replicateTools like Gong, Zapier, and Handwrytten in actionIf you’re looking for a way to stand out in a sea of digital sameness, this episode’s for you. Subscribe and stick around—we’re just getting started.Support the show+++++++++++++++++Like/Subscribe/Review:If you are getting value from the show, please follow/subscribe so that you don't miss an episode and consider leaving us a review. Website:For more information about the show or to get in touch, visit DigitalCustomerSuccess.com. Buy Alex a Cup of Coffee:This show runs exclusively on caffeine - and lots of it. If you like what we're, consider supporting our habit by buying us a cup of coffee: https://bmc.link/dcspThank you for all of your support!The Digital Customer Success Podcast is hosted by Alex Turkovic🎬 This content was edited by Lifetime Value Media.Learn more at: https://www.lifetimevaluemedia.com
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The Art of Collaboration in Digital CS with Holly Goodliffe | Episode 096
Digital CS consultant Holly Goodliffe joins the Digital CX podcast to share her journey from the nonprofit world to tech leadership and discuss the evolving role of digital CS in complex, stakeholder-rich environments. She and Alex explore how simplifying digital engagement, deploying timely CTAs, and adopting a Scrum mindset can empower teams to drive smarter, scalable customer experiences.Chapters:Complexity, stakeholders, and collaboration Navigating toes and turf wars Building trust through shared strategy Key traits of successful digital leaders What Holly’s clients are asking for now Digital doesn’t have to be daunting Spotify Wrapped vibes for B2B The data dilemma and simple starts Omnichannel kindergarten vs. strategy The art of simple, timely CTAs Scrum mindset for digital execution Staying smart with content and courage Enjoy! I know I sure did…Holly's Linkedin: https://www.linkedin.com/in/hollygoodliffe/ Support the show+++++++++++++++++Like/Subscribe/Review:If you are getting value from the show, please follow/subscribe so that you don't miss an episode and consider leaving us a review. Website:For more information about the show or to get in touch, visit DigitalCustomerSuccess.com. Buy Alex a Cup of Coffee:This show runs exclusively on caffeine - and lots of it. If you like what we're, consider supporting our habit by buying us a cup of coffee: https://bmc.link/dcspThank you for all of your support!The Digital Customer Success Podcast is hosted by Alex Turkovic🎬 This content was edited by Lifetime Value Media.Learn more at: https://www.lifetimevaluemedia.com
About The Digital CX Podcast: Driving digital customer success and outcomes in the age of A.I.
This podcast is for Customer Experience leaders and practitioners alike; focused on creating community and learning opportunities centered around the burgeoning world of Digital CX.Hosted by Alex Turkovic, each episode will feature real and in-depth interviews with fascinating people within and without the CS community. We'll cover a wide range of topics, all related to building and innovating your own digital CS practices. ...and of course generative AI will be discussed.If you enjoy the show, please subscribe, follow, share and leave a review. For more information visit https://digitalcustomersuccess.com
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