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
How Disqo Sparked an AI Movement With a Company-Wide HackathonWhen 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 they achieved this and how it transformed their culture. From creating starter ideas and cross-functional teams to sustaining momentum with office hours and grassroots initiatives, David lays out the exact playbook you can use to kickstart AI adoption in your own org.What you’ll learn:- How to design an AI hackathon that drives real business outcomes.- Why constraints and scoring criteria make or break innovation.- How to spark bottom-up energy with top-down support.- Ways to sustain momentum with AI office hours and team-led mini-hackathons.- Why AI adoption starts with leaders using the tools themselves.Check out the Key Takeaways & Transcripts: https://www.gainsight.com/presents/series/unchurned/Where to Find David:LinkedIn - https://www.linkedin.com/in/davidalankarp/Where to Find Josh: LinkedIn: https://www.linkedin.com/in/jschachter/In this episode, we cover:0:00 – Preview & Introduction1:56 – Meet David Karp, CCO of Disqo2:50 – Disqo’s AI Journey: Where It All Began4:00 – Seeding Ideas: Building the Hackathon Foundation7:09 – The Secret Sauce: Rules, Constraints & Incentives11:40 – Behind the Scenes: Planning Hackathon Logistics16:22 – Scoring, Evaluation & The Prize That Motivated Teams19:19 – How Disqo Ran an Internal CS Hackathon21:35 – Keeping Momentum Alive After the Event23:28 – Outcomes: The Lasting Impact of the Hackathon24:00 – Key Lessons for CS Leaders & SaaS Executives
The Secret Workflow Letting LeeRon Manage 100 Accounts With a 2-Person TeamWhen tasked with managing 100 accounts with just two people, most leaders would immediately start hiring. Not LeeRon Yahalomi. Instead, the VP of Customer Success at Aligned built her own team of AI agents inside ChatGPT that handle customer handoffs, meeting prep, and even communication coaching.In this mind-opening conversation, LeeRon shares how she scaled her team without adding headcount, how she uses AI to deliver “11-star” customer experiences, and why she believes customer success is no longer about post-sales; it’s about the next sale. Whether you’re an AI skeptic or already experimenting with agents, this episode will change how you think about scaling teams, designing workflows, and the future of CS.What you’ll learn:1. Why AI agents are the new teammates in customer success.2. How to use ChatGPT for handoffs, prep, and communication.3. Why CS is not just “post-sales”.4. How to balance AI automation with human empathy.5. How Customer Success can drive revenue when it focuses on expansion, not just retention.Check out the Key Takeaways & Transcripts: https://www.gainsight.com/presents/series/unchurned/Where to Find LeeRon YahalomiLinkedIn - https://www.linkedin.com/in/leeron-yahalomi-1b066819/Where to Find Josh: LinkedIn: https://www.linkedin.com/in/jschachter/In this episode, we cover:0:00 - Preview1:32 - Meet LeeRon Yahalomi & Learn about Aligned's mission 3:31 - The thrill of working in early-stage startups4:55 - Why AI became the only path to growth11:00 - Will AI replace jobs in CS?13:20 - AE to CS Handoff Agent17:55 - Meeting Preparation Agent20:57 - Communication Coaching Agent23:20 - Orchestration CS with Agent26:26 - Prioritising learning AI28:28 - Why CS isn’t post-sales anymore; it’s the “next sale”Referenced:- ChatGPT: https://chatgpt.com/- n8n: https://n8n.io/
How Kalpana, our Enterprise CSM, Scaled Her Book of Business by 40% With AIKalpana Krishna Kumar, an Enterprise CSM at Gainsight, and Brady Bluhm, Senior Product Manager at Gainsight, join the show to share how they’re reimagining customer success with AI. From Kalpana’s 40% increase in her book of business to Brady’s unlikely journey from child actor to AI trailblazer, this episode is full of surprising stories about scaling, stress relief, and the human side of AI. Together, they reveal how AI is less about automation and more about unlocking the best version of yourself.What you’ll learn:1. How Kalpana scaled her accounts by 40% without burning out.2. Why peace of mind is one of AI’s most underrated benefits.3. The grassroots AI movement that transformed Gainsight.4. Brady’s personal workflow hacks for integrating AI into daily work.5. Why AI isn’t replacing CSMs—it’s making them stronger.Check out the Key Takeaways & Transcripts: https://www.gainsight.com/presents/series/unchurned/Where to Find Brady Bluhm LinkedIn - https://www.linkedin.com/in/bradybluhm/IMDb - https://www.imdb.com/name/nm0089603/Where to Find Kalpana Krishna Kumar LinkedIn - https://www.linkedin.com/in/kalpana-krishna-kumar/Where to Find Josh: LinkedIn: https://www.linkedin.com/in/jschachter/In this episode, we cover:0:00 - Preview1:00 - Meet Brady & Kalpana3:35 - First steps with AI 8:24 - Grassroots AI education at Gainsight10:50 - Scaling book of business by 40% 17:13 - Why AI gives CSMs peace of mind19:01 - Find a meeting recording tool24:34 - Predicting the future of CS25:05 - Building personal AI agents & say goodbye to busy work 35:03 - Closing reflectionsReferenced:- Staircase AI - https://www.gainsight.com/staircase-ai/- Gamma - https://gamma.app/- NotebookLM - https://notebooklm.google/- Claude - https://claude.ai/- Zoom AI Companion - https://www.zoom.com/en/products/ai-assistant/
AI is evolving so fast that it’s hard to keep up—sparking both excitement and anxiety about the future of work. Will AI replace jobs, or will it redefine them?In this episode of [Un]churned, host Josh Schachter, SVP of Atlas at Gainsight, sits down with Jeffrey Bussgang, General Partner & Co-Founder at Flybridge Capital Partners and Senior Lecturer at Harvard Business School, and Teresa Anania, Chief Customer Officer at Sophos, who’s been leading from the frontlines of AI-driven customer engagement. Together, they unpack the gap between the theory of AI transformation and the reality of implementation in large organizations. Jeff discusses how leaders can foster an “AI native” culture—one that encourages experimentation while valuing human judgment. Teresa shares a candid look into Sophos' AI journey, addressing the fears, resistance, and cultural shifts that come with change. She also highlights practical strategies to empower teams and enhance customer experiences through thoughtful automation.Whether you’re a tech leader, customer success pro, or just AI-curious, this conversation is packed with actionable insights on embracing the future without losing the human touch.Timestamps: 0:00 - Preview0:48 - Meet Jeff & Teresa2:40 - The Impact of AI on Business Innovation5:00 - Fostering an AI-Driven Culture to Elevate Workforce Value16:10 - How AI Enables Rapid Prototyping19:40 - Balancing Human and AI Workflows21:50 - Quality Assurance and Customer Experience at Scale27:50 - Internal “Agent Assist” Solutions35:07 - Dynamics in Adopting AI Solutions______________________👉 Follow the podcast Subscribe: https://www.youtube.com/@GainsightApple Podcast: https://apple.co/3dfWXmDSpotify: https://spoti.fi/3KD3Ehl👉 Explore more episodes, takeaways & transcripts: https://gainsight.com/unchurned👉 Connect with the guestsJeffrey Bussgang: https://www.linkedin.com/in/bussgang/Teresa Anania: https://www.linkedin.com/in/teresa-anania/Check out Jeff's Book “The Experimentation Machine": https://experimentationmachine.com/👉 Connect with hostJosh Schachter: https://www.linkedin.com/in/jschachter/ ______________________[Un]Churned is presented by Gainsight About GainsightGainsight is the retention engine behind the world’s most customer-centric companies. The Gainsight CustomerOS platform orchestrates the customer journey from onboarding to outcomes. More than 2,000 companies trust Gainsight’s applications and AI agents to drive learning, adoption, community connection, and success for their customers. Learn more at www.gainsight.com.
Meet Chuck Ganapathi, the new CEO of Gainsight!In this special episode of [Un]Churned, host Josh Schachter sits down with Gainsight’s outgoing CEO Nick Mehta and his successor, Chuck Ganapathi, to mark a pivotal leadership transition. Nick reflects on his 13-year journey building Gainsight into a category-defining company, the lessons he’s learned navigating growth, and why now is the right time to hand over the reins. Chuck shares his gratitude for the opportunity, the deep trust he and Nick have built over decades of connection, and his vision for the company’s next chapter—one shaped by AI, customer success innovation, and a human-first culture.Timestamps0:00 - Welcome & The Big Announcement2:25 - Why Nick Is Stepping Down3:54 - Lessons from Private Equity & Building a Lasting Company6:23 - Chuck on becoming the NEW CEO7:10 - How Nick & Chuck First Met (Stanford Days & Startup Stories)16:25 - Why Chuck Was the Obvious Choice for CEO21:12 - CEO Transitions as Turning Points25:40 - Human-First Leadership & Gainsight’s Mission28:20 - What’s Next for Customer Success in the Age of AI 34:12 - Will AI Replace CSMs? (Nick & Chuck’s Take)36:42 - Looking Ahead: The Next Chapter of Gainsight38:52 - Fun Facts About Chuck (Heartthrob, Tennis & Shopping!)44:34 - Final Words: Legendary & Transformational Futures👉 Explore more episodes, takeaways & transcripts: https://gainsight.com/unchurned👉 Check out the bonus episode: https://gainsight.com/unlock______________________👉 Follow the podcast Subscribe: https://www.youtube.com/@GainsightApple Podcast: https://apple.co/3dfWXmDSpotify: https://spoti.fi/3KD3Ehl👉 Connect with the guestsChuck Ganapathi: https://www.linkedin.com/in/chuckganapathi Nick Mehta: https://www.linkedin.com/in/nickmehta/👉 Connect with hostJosh Schachter: https://www.linkedin.com/in/jschachter/ ______________________Keywords: Gainsight, Customer Success, Nick Mehta, Chuck Ganapathi, CEO Transition, Customer Retention, SaaS Leadership, AI in Customer Success, AI Agents, Business Growth, Human-First Leadership, Churn Reduction, Scale Customer Success, SaaS Leadership Podcast, SaaS Growth Strategies______________________[Un]Churned is presented by Gainsight About GainsightGainsight is the retention engine behind the world’s most customer-centric companies. The Gainsight CustomerOS platform orchestrates the customer journey from onboarding to outcomes. More than 2,000 companies trust Gainsight’s applications and AI agents to drive learning, adoption, community connection, and success for their customers. Learn more at www.gainsight.com.
#updateai #customersuccess #saas #business Welcome back to Unchurned! In this special episode, hosts Josh Schachter and Kristi Faltorusso gather for one last on-air session before a well-deserved summer break—and just before Josh’s London wedding celebration! They also dive into Kristi's AI learning journey—breaking down how she’s gone all-in on micro-learning, prompt engineering, and building real tools with zero engineering background. Listen as she and Josh discuss the importance of actually using AI, not just reading about it, the potential risks of ignoring these skills, and why investing just ten minutes a day could change your game in the evolving tech landscape.Timestamps0:00 - Preview 0:45 - Josh is married/is getting married4:30 - Upcoming summer break for the podcast5:05 - Leadership Loss and Reflections at Planhat8:07 - Kristi is learning & experimenting with AI13:55 - Scaling Personal Expertise with AI18:40 - Encouragement to Engage with AI___________________________👉 Follow the podcast Youtube: https://www.youtube.com/@updateai9697Apple Podcast: https://apple.co/3dfWXmD Spotify: https://spoti.fi/3KD3Ehl👉 Connect with hostsJon Johnson: https://www.linkedin.com/in/jonwilliamjohnson/Kristi Faltorusso: https://www.linkedin.com/in/kristiserrano/Josh Schachter: https://www.linkedin.com/in/jschachter/👉 Sign up for UpdateAI👉 Be the first to know when a new episode of Unchurned is dropped. Sign up for our newsletter at https://blog.update.ai/______________________Unchurned is presented by UpdateAIAbout UpdateAIAt UpdateAI our mission is to empower CS teams to build great customer relationships. We work with early & growth-stage B2B SaaS companies to help them scale CS outcomes. Everything we do is devoted to removing the overwhelm of back-to-back customer meetings so that CSMs can focus on the bigger picture: building relationships.
#updateai #customersuccess #saas #businessRachel Tsui, the ex-Head of CS at Komodo Health, joins hosts Jon Johnson and Josh Schachter to dive deep into the intricacies of customer success. Rachel highlights the innovative use of healthcare data to identify patient trends and enhance service delivery. The conversation explores how Komodo's customer success team navigates post-sales processes, strategically collaborates with account management, and the essential role of data-driven decisions. Jon and Rachel also delve into career growth challenges, touching on the balancing act of flat organization structures, professional development, and the evolving expectations of newer workforce generations. Join us for a captivating journey through customer success strategies, organizational dynamics, and how they shape the future of innovation at Komodo Health.Timestamps0:00 - Preview, & Intros7:30 - CS at Komodo Health 10:28 - KPIs for customer success at Komodo12:00 - Plans and Priorities 13:22 - Focusing on separating support from CS activities16:03 - Managing expectations around promotions20:06 - Navigating career growth23:50 - Cross-functional collaboration and tools for knowledge sharing___________________________👉 Follow the podcast Youtube: https://youtu.be/JprAz-o-dWkApple Podcast: https://apple.co/3dfWXmD Spotify: https://spoti.fi/3KD3Ehl👉 Connect with the guestRachel Tsui: https://www.linkedin.com/in/racheltsui👉 Connect with hostsJon Johnson: https://www.linkedin.com/in/jonwilliamjohnson/Kristi Faltorusso: https://www.linkedin.com/in/kristiserrano/Josh Schachter: https://www.linkedin.com/in/jschachter/👉 Sign up for UpdateAI 👉 Be the first to know when a new episode of Unchurned is dropped. Sign up for our newsletter at https://blog.update.ai/________________Keywords: How to keep your customers happy, customer success manager, healthcare map, health data, AI, big data, Komodo Health, customer success, net dollar retention, CSM, customer engagement, healthcare platform, data platform, CS team, account management, product utilization, strategic initiatives, executive relationships, customer influence, renewal rate, Gainsight, CRM, AMs (Account Managers), team structure.______________________Unchurned is presented by UpdateAIAbout UpdateAIAt UpdateAI our mission is to empower CS teams to build great customer relationships. We work with early & growth-stage B2B SaaS companies to help them scale CS outcomes. Everything we do is devoted to removing the overwhelm of back-to-back customer meetings so that CSMs can focus on the bigger picture: building relationships.
#updateai #customersuccess #saas #businessJoin host Josh Schachter, Co-Founder & CEO of UpdateAI, as he sits down with Cait Keohane, the Chief Customer Officer of Airtable, to explore the art of scaling world-class post-sale experiences. Cait shares her incredible journey from being one of the early employees at Zendesk and helping grow the company into a multibillion-dollar powerhouse, to stepping into her new leadership role at Airtable. Together, they explore what it takes to build robust customer management systems from the ground up, the importance of listening directly to customers, and how organizations can balance high-touch service with operational efficiency.Timestamps00:00 – Preview, Meet Cait Keohane & Learn About Airtable01:30 – Cait's Journey at Zendesk03:15 – Building Customer Success and Account Management at Zendesk07:50 – Joining Airtable as CCO08:50 – First 90 Days at Airtable: Priorities and Execution13:10 – Feedback and Voice of Customer Mechanisms15:00 – Renewal Management and Risk Mitigation19:38 – Delivering Personalized Experiences at Scale21:50 – Platform Complexity and Change Management24:50 – The Role of MVP Users and Power Builders in Scaling26:51 – Closing Thoughts and Future Outlook___________________________👉 Follow the podcast Youtube: https://www.youtube.com/@updateai9697Apple Podcast: https://apple.co/3dfWXmDSpotify: https://spoti.fi/3KD3Ehl👉 Connect with the guest Cait Keohane: https://www.linkedin.com/in/caitkeohane/👉 Connect with hostsJosh Schachter: https://www.linkedin.com/in/jschachter/👉 Sign up for UpdateAI 👉 Be the first to know when a new episode of Unchurned is dropped. Sign up for our newsletter at https://blog.update.ai/________________Keywords: How to keep your customers happy, customer success manager, customer support, customer success management, Customer Success Manager role, hiring tips for customer success, customer success metrics, Customer success strategies for SaaS companies, Building a customer-centric culture in tech, Scaling customer success teams effectively, Customer feedback integration in product strategy, Airtable's approach to customer success and retention, Airtable customer insights, Customer journey mapping, Product strategy feedback______________________Unchurned is presented by UpdateAIAbout UpdateAIAt UpdateAI our mission is to empower CS teams to build great customer relationships. We work with early & growth-stage B2B SaaS companies to help them scale CS outcomes. Everything we do is devoted to removing the overwhelm of back-to-back customer meetings so that CSMs can focus on the bigger picture: building relationships.
#updateai #customersuccess #saas #businessWelcome back to Unchurned! In this very special annual tradition, host Josh Schachter, CEO of UpdateAI sits down with Nick Mehta, the ever-energetic CEO of Gainsight, for a deep dive into all things Pulse 2025 - Gainsight’s CS conference, which this year is bringing its signature blend of learning and community to Las Vegas. Josh and Nick reminisce about Pulse’s humble beginnings, reflect on the journey from a simple luncheon to a high-octane Vegas affair, and tease this year’s theme (wardrobe predictions included!).You’ll also get an exclusive inside look at Gainsight, with Nick sharing candid insights about new faces on the leadership team, the integration of exciting new products like Staircase, ModerateKit, and Skilljar, and how the company is weaving AI into both its offerings and internal processes. The conversation is equal parts fun and insightful, filled with plenty of laughs and a motivating message for customer success pros to embrace innovation and lean into the future.Timestamps0:00 - Preview & Introductions1:25 - Pulse Conference in Las Vegas8:36 - Reflections on New & Evolving Leadership 15:23 - Recent Innovations & Acquisitions24:10 - Operational Shifts and AI Integration30:12 - Looking Ahead & Closing Thoughts___________________________👉 Follow the podcast Youtube: https://www.youtube.com/@updateai9697Apple Podcast: https://apple.co/3dfWXmD Spotify: https://spoti.fi/3KD3Ehl👉 Connect with the guest Nick Mehta: https://www.linkedin.com/in/nickmehta👉 Connect with hostsJon Johnson: https://www.linkedin.com/in/jonwilliamjohnson/Kristi Faltorusso: https://www.linkedin.com/in/kristiserrano/Josh Schachter: https://www.linkedin.com/in/jschachter/👉 Sign up for UpdateAI 👉 Be the first to know when a new episode of Unchurned is dropped. Sign up for our newsletter at https://blog.update.ai/______________________Unchurned is presented by UpdateAIAbout UpdateAIAt UpdateAI our mission is to empower CS teams to build great customer relationships. We work with early & growth-stage B2B SaaS companies to help them scale CS outcomes. Everything we do is devoted to removing the overwhelm of back-to-back customer meetings so that CSMs can focus on the bigger picture: building relationships.