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:

LinkedIn: https://www.linkedin.com/in/jennycalvert/

Ready to churn less and win more? 🏆 Subscribe for a monthly roundup of every episode at ⁠⁠gainsight.com/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:

* 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.

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:

- 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 & 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/