- Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned
The customer success landscape is about to shift dramatically. Kristi Faltorusso, fresh off her departure from ClientSuccess after five years, reveals the three trends that will define CS in 2026—and the second one might surprise you. From the explosion of CS Ops to the "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.
---
Timestamps
0:00 - Preview & Introduction
1:23 - Kristi is back!
2:34 - Why Kristi Left a Perfect Job?
5:20 - What She'll Miss Most
6:50 - Building Unbreakable Trust with Leadership
9:20 - Kristi's Next Chapter
10:35 - Kristi's 2026 Predictions for CS
13:13 - The ERR Apocalypse & The Consolidation Wave
15:45 - The Rebranding of CS Ops Roles
18:15 - Kristi's Vibe Coding Journey
21:30 - Make AI Learning Fun
25:00 - Find and Champion Your AI Champions
26:10 - 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:
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/unchurned
Every major transformation Yvette Hill has led started the same way: with a moment of panic.
Across a 35-year career at IBM, Xerox, Microsoft, and now F5, Yvette Hill, SVP of Customer Success and Global Renewal Sales at F5, has repeatedly observed the same pattern: big deals 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.
---
Timestamps
0:00 - 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 Hill
LinkedIn: https://www.linkedin.com/in/yvette-hill-smith-0374265/
---
Where to Find Jenny:
Ready to churn less and win more? 🏆 Subscribe for a monthly roundup of every episode at gainsight.com/unchurned
Two of SaaS's most influential voices just sounded the same alarm: Cassie Young, General Partner at Primary Ventures, and Kyle Poyar, founder of Growth Unhinged, both published viral articles warning of a "gross retention apocalypse" in AI-powered SaaS.
Cassie's 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.
---
Timestamps
0:00 - Preview & Introduction
1:36 - Meet Cassie Young & Kyle Poyar
3:00 - The Gross Retention Apocalypse & AI Churn Wave
7:25 - ERR vs ARR: The Red Herring - 9 out of 10 Customers Stopped Using
10:00 - Series A's Done on "Vibes"
11:05 - What Investors Are Looking For
14:40 - The Cluely Controversy: Distribution vs Product Quality
16:15 - Why Fast Growth Means Nothing Without Retention Data
21:15 - Customer Success as a Core Operating Philosophy
29:30 Forward Deployed Engineers as Part of Sales Motion
31:40 - Most Overrated Metric
32:08 - Most Underrated Metric
33:10 - SaaS Principles That Will Last 10 Years
35:30 - 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/id1842238102
Where to Find Cassie Young
LinkedIn: 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-renaissance
Kyle'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.
---
Timestamps
0:00 – Preview & Introduction
1:22 – Meet Alexis Hennessy: Partner at Heidrick & Struggles
2:02 – Many CEOs Still Don’t Know What They Want
4:10 – What CEOs Want in a CCO
5:16 – What Great CCO Candidates Do in Interviews
6:15 – Why CCO Hiring Is Surging Again
7:25 – What Sets VP Candidates Apart When They Want to Move Up
9:00 – Are Boards Demanding AI Experience?
10:45 – What the Best CCO Hires Do in Their First Year
12:45 – Personality Traits That Define High-Performing CCOs
13:43 – Agentic AI, Consumption Models & the New Stakes for CCOs
15:23 – Can CCOs Become CEOs?
18:28 – Predictions: The Future of the CCO Role
19:23 – 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.
---
Timestamps
0:00 – Preview
0:58 – Meet Erica Kuhl: EVP at Gainsight & Former Employee #176 at Salesforce
3:39 – What Early Salesforce Adoption Actually Looked Like
6:25 – Teaching Admins Before Admins Existed
9:40 – Why Erica Pitched a Community Before “Community” Was a Thing
11:25 – Building the First Salesforce Community
13:43 – Scaling Without Support
19:30 – How Community Became a Strategic Retention Lever
24:44 – Defining Digital Customer Success
26:35 – Where to Start: Crawl–Walk–Run for Digital CS
30:25 – Why Community Multiplies GRR
31:28 – 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 Lock
Where to Find Josh:
LinkedIn: https://www.linkedin.com/in/jschachter/
---
Resources Mentioned:
* Brian Oblinger’s Community Strategy Academy
* Skilljar
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.
Timestamps
0:00 – Preview & Introduction
0:57 – Meet Colin Slade and the Situation at Cloudbeds
9:25 – Mitigating Team Fears Around AI Replacing Jobs
13:13 – The Stepwise Approach to Implementing AI
19:50 – Scaling Securely: Working with IT, Risk-Taking, and Adoption
24:00 – Roles and Team Structure for Effective AI Operations
33:10 – Documentation as a Hidden Bottleneck
39:45 – Build vs. Buy: Why Cloudbeds Built In-House
42:20 – The Impact and a Culture of Fearless Experimentation
What 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/app
Lovable – 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 success
Timestamps:
0:00 – Preview & Intro
1:02 – Meet Kat Valverde
1:42 – What buyers and sellers say in enterprise AI roundtables
3:11 – The challenge of internal adoption
6:20 – The 15-Minute Rule; a 4-week micro-adoption framework
11:45 – The psychology behind AI adoption
12:18 – 2–3× adoption rates and major cost savings
14:45 – Closing thoughts
Key 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.
Timestamps
0:00 – Preview & Introduction
1:19 – Meet Mark Roberge: Co-Founder, Stage 2 Capital
2:45 – The Early Days of AI in GTM
6:33 – What’s Slowing Down AI Adoption
8:00 – Why Most AI Startups Are Still Too Iterative
12:00 – The "Agentic" Shift: From Co-Pilots to Autonomous Agents
14:15 – The 4 Phases of AI Go-to-Market Evolution
20:35 – Managing Your Agents: The New CRO Skillset
26:00 – Deciding the ICP: It’s Not CAC
29:35 – How AI Breaks Down Department Silos
35:40 – 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?"
Timestamps
0:00 - Preview & Introduction
1:48 - Meet Jacob & An Overview of Relay.app
4:08 - From Stanford AI Research to Google to Founder
4:57 - AI Agents were 15 Years in the Making
8:30 - It Took 2.5 Years to Get the First Customer
12:35 - What Actually Is Agentic AI?
14:55 - Understanding AI Agents
19:45 - How AI Accesses Information: Context Windows, and RAG
24:11 - The Shift from RAG to MCP
25:51 - Understanding MCP: The Restaurant Analogy
30:04 - 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 Enterprises
42:12 - The Two Limitations of Agents Today
44:31 - We're All Managers Now
46:15 - Where to Stay Current on AI
47:36 - The Value of Hands-On Experience with AI Tools
What 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:
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 & Introduction
1:24 – Meet Chad & Omer
2:10 – Pulse Local Events and Building the CS Community
3:52 – Chad’s Origin Story: Being an Early CS Ambassador
4:55 – From Customer Cheerleading to Value Creation
12:45 – The AI Revolution and the Return of Strategic CSMs
18:31 – How Outcome-Based CS Influences Revenue
23:53 – Defining Success Is a Challenge
25:25 – How AI Analyzes Survey Data to Find Customer Sentiment
28:10 – Customizing Product Updates for Customers
29:25 – Tactical Advice for CSMs
30:35 – 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 Renewals
12:05 - Why CS Is a Financial Business First — The Real Definition of Customer Value
15:19 - CS to CPO: 3 Game-Changing Skills That Make the Transition Possible
17:05 - CS vs. Product: The Emotional Shift No One Talks About
19:51 - PathFactory’s Big Vision — Connecting Content Directly to Revenue (With AI!)
22:28 - Why Websites Are Dying — And What’s Replacing Them
25:35 - Truth, Transparency & Trust: What We Owe Each Other in the AI Era
26:51 - The AI Adoption Problem: Why CS Teams Struggle With Change Management
31:35 - 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 products
2. Why AI-powered engagement signals are replacing time-based customer outreach
3. The importance of building trust in AI-powered insights before teams will adopt them
4. How to aggregate and visualize data from multiple systems to tell a coherent story to stakeholders
5. Why change management is critical when introducing new product features that alter established workflows
6. 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 Automation
5:32 - Sean MacPherson: Aggregating insights from multiple systems
9:48 - Tiffany Taylor: Speed up feedback loops and time-to-value
14:09 - Matt Krebsbach: Prioritization, delivering outcomes and data enablement
18:47 - Charlie Ferraro: Retention, renewals and efficiency
20:35 - From Spidey sense to AI-powered engagement analysis
21:47 - Measuring adoption in agentic products
22:07 - Margo Martin: Stay ahead with real-time defect alerts
25:17 - The value of relationship-level insights
26:10 - Tony Pante: Driving adoption across 2,000 CSMs at SAP
29:35 - Using AI for translation, content creation, and enablement
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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 world
Check out the Key Takeaways & Transcripts: https://www.gainsight.com/presents/series/unchurned/
Where to Find the Guest
Brett'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 & Introduction
1:18 - Meet Chuck & Brett
3:30 - How Brett and Chuck met at Siebel
9:28 - Transition to Salesforce: destruction of Siebel as a goal
14:11 - Changing Nature of Product Marketing in the AI Era
18:00 - Systems of Record vs. Systems of Action
21:13 - Databases as “lossy” representations of reality
29:00 - 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 agents
47:17 - 10x CSMs enabled by AI agents
References:
- Brett Queener's blog: https://queener.substack.com/
How Human-Centric AI Frees CSMs for Strategic Work at BMC
Leading customer success at a global scale is never easy—especially after a company split. For Sofia Barbosa, this meant steering a leaner team while still supporting hundreds of BMC products worldwide. The challenge: deliver more impact with fewer hands. The solution: build Succedo, an AI platform that reimagined how her team worked. The 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 & Introduction
1:40 – Meet Sofia Barbosa (CCO, BMC Software)
3:15 – Sofia’s promotion and the BMC split
6:53 – Why & how Succedo was born
11:30 – The impact of using Succedo
12:55 – Using AI to create value summaries
15:40 – Creating personalized training paths with AI
18:35 – AI for support: prioritization and sentiment analysis
21:18 – Automating statements of work with AI
24:35 – Building “Succedo Forge” and “Succedo Care” teams
27:10 – Managing change and team sentiment around AI
28:45 – Advice for CCOs driving AI transformation
Referenced:
- 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 Hackathon
When everyone was talking about AI but few knew where to start, Disqo took a bold step: they cleared two full days and ran a company-wide AI hackathon. The result? 70 people, 15 teams, and a wave of innovation that’s still driving value today.
In this episode, David Karp, Chief Customer Officer at Disqo, shares the inside story of how 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 & Introduction
1:56 – Meet David Karp, CCO of Disqo
2:50 – Disqo’s AI Journey: Where It All Began
4:00 – Seeding Ideas: Building the Hackathon Foundation
7:09 – The Secret Sauce: Rules, Constraints & Incentives
11:40 – Behind the Scenes: Planning Hackathon Logistics
16:22 – Scoring, Evaluation & The Prize That Motivated Teams
19:19 – How Disqo Ran an Internal CS Hackathon
21:35 – Keeping Momentum Alive After the Event
23:28 – Outcomes: The Lasting Impact of the Hackathon
24:00 – Key Lessons for CS Leaders & SaaS Executives
The Secret Workflow Letting LeeRon Manage 100 Accounts With a 2-Person Team
When 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 Yahalomi
LinkedIn - 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 - Preview
1:32 - Meet LeeRon Yahalomi & Learn about Aligned's mission
3:31 - The thrill of working in early-stage startups
4:55 - Why AI became the only path to growth
11:00 - Will AI replace jobs in CS?
13:20 - AE to CS Handoff Agent
17:55 - Meeting Preparation Agent
20:57 - Communication Coaching Agent
23:20 - Orchestration CS with Agent
26:26 - Prioritising learning AI
28:28 - 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 AI
Kalpana Krishna Kumar, an Enterprise CSM at Gainsight, and Brady Bloom, 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 - Preview
1:00 - Meet Brady & Kalpana
3:35 - First steps with AI
8:24 - Grassroots AI education at Gainsight
10:50 - Scaling book of business by 40%
17:13 - Why AI gives CSMs peace of mind
19:01 - Find a meeting recording tool
24:34 - Predicting the future of CS
25:05 - Building personal AI agents & say goodbye to busy work
35:03 - Closing reflections
Referenced:
- 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 - Preview
0:48 - Meet Jeff & Teresa
2:40 - The Impact of AI on Business Innovation
5:00 - Fostering an AI-Driven Culture to Elevate Workforce Value
16:10 - How AI Enables Rapid Prototyping
19:40 - Balancing Human and AI Workflows
21:50 - Quality Assurance and Customer Experience at Scale
27:50 - Internal “Agent Assist” Solutions
35:07 - Dynamics in Adopting AI Solutions
______________________
👉 Follow the podcast
Subscribe: https://www.youtube.com/@Gainsight
Apple Podcast: https://apple.co/3dfWXmD
Spotify: https://spoti.fi/3KD3Ehl
👉 Explore more episodes, takeaways & transcripts: https://gainsight.com/unchurned
👉 Connect with the guests
Jeffrey 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 host
Josh Schachter: https://www.linkedin.com/in/jschachter/
______________________
[Un]Churned is presented by Gainsight
About Gainsight
Gainsight 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.
Timestamps
0:00 - Welcome & The Big Announcement
2:25 - Why Nick Is Stepping Down
3:54 - Lessons from Private Equity & Building a Lasting Company
6:23 - Chuck on becoming the NEW CEO
7:10 - How Nick & Chuck First Met (Stanford Days & Startup Stories)
16:25 - Why Chuck Was the Obvious Choice for CEO
21:12 - CEO Transitions as Turning Points
25:40 - Human-First Leadership & Gainsight’s Mission
28:20 - 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 Gainsight
38:52 - 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/@Gainsight
Apple Podcast: https://apple.co/3dfWXmD
Spotify: https://spoti.fi/3KD3Ehl
👉 Connect with the guests
Chuck Ganapathi: https://www.linkedin.com/in/chuckganapathi
Nick Mehta: https://www.linkedin.com/in/nickmehta/
👉 Connect with host
Josh 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 Gainsight
Gainsight 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.
Timestamps
0:00 - Preview
0:45 - Josh is married/is getting married
4:30 - Upcoming summer break for the podcast
5:05 - Leadership Loss and Reflections at Planhat
8:07 - Kristi is learning & experimenting with AI
13:55 - Scaling Personal Expertise with AI
18:40 - Encouragement to Engage with AI
___________________________
👉 Follow the podcast
Youtube: https://www.youtube.com/@updateai9697
Apple Podcast: https://apple.co/3dfWXmD
Spotify: https://spoti.fi/3KD3Ehl
👉 Connect with hosts
Jon Johnson: https://www.linkedin.com/in/jonwilliamjohnson/
Kristi Faltorusso: https://www.linkedin.com/in/kristiserrano/
Josh Schachter: https://www.linkedin.com/in/jschachter/
👉 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 UpdateAI
About UpdateAI
At 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.