Heading to Vegas this May? Join Josh at Pulse 2026 and come say hi—your oversized fluorescent daiquiri is on him. No catch.

Grab your ticket at gainsightpulse.com and use code UNCHURNED for a special rate.

What does the future of CS actually look like? Ghazi Masood, CRO of Replit, has some strong opinions and the growth numbers to back them up.

In one year, Replit went from $2M to $150M in revenue. Now they're targeting $1B. And while most companies are still debating AI strategy, Ghazi is already rebuilding his entire GTM org around it — scaling from 40 to 230 people, scrapping the traditional CSM model, and betting that the next billion software creators won't write a single line of code.

In this episode, Ghazi breaks down how he's building post-sales for the AI era, why he replaced CSMs with "product advocates," and what it looks like when your entire team builds their own tools — including their own version of Clari and a customer health dashboard, both built on Replit itself.

He also shares his take on the future of SaaS, how enterprises are quietly wrapping AI layers on top of Salesforce and Workday, and why Cursor, Claude, and OpenAI aren't keeping him up at night.

If you're in Customer Success, Revenue, or CS Ops, this episode will challenge how you think about your role.

---

Timestamps

0:00 - Preview & Introduction

1:25 - Meet Ghazi Masood & Overview of Replit

4:40 - Building the GTM infrastructure

7:30 - How anyone at Replit can build internal tools

9:00 - Managing chaos when everyone becomes a creator

12:40 - Enterprise security & governance guardrails

15:47 - Are Cursor, Claude & OpenAI real competitors?

18:10 - Usage-based pricing explained

19:17 - Post-sales strategy for non-technical users

23:53 - Hiring 200 people in 12 months

24:40 - The future of SaaS

26:56 - SMBs replacing Workday and Tableau with Replit

30:40 - Lessons from Auth0 and Retool

32:32 - What Ghazi looks for when hiring

---

What You’ll Learn

- What enterprise customers are quietly building on top of their existing SaaS tools — and what it means for vendors

- How SMBs are replacing Workday, Tableau, and traditional CRMs entirely by building on Replit

- How to handle churn when 90% of your users have zero technical background

- The governance and security guardrails that got Replit into financial services and government accounts

- How to structure a GTM catalog library so your team stops duplicating each other's work

- Ghazi's take on whether SaaS is dying — and why the answer is completely different depending on company size

- Why product passion matters more to Ghazi than years of sales experience when hiring

- How Replit thinks about competitive threats from Cursor, Claude Code and OpenAI — and why they're not losing sleep over any of them

---

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.

---

Where to Find Ghazi Masood

LinkedIn: https://www.linkedin.com/in/ghazi-masood-09195a2/

---

Where to Find Josh:

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

Unchurned Substack: https://unchurned.substack.com/

Heading to Vegas this May?

Join Josh at Pulse 2026 and come say hi—your oversized fluorescent daiquiri is on him. No catch.

Grab your ticket at gainsightpulse.com and use code UNCHURNED for a special rate.

CS is going through an identity crisis.

Is it product? Is it relationships? Is it revenue?

According to Cassie Vaughn (RVP of CS at monday.com)… it’s now all three, and AI is forcing it to be so.

In this episode of Unchurned, Cassie breaks down what’s actually changing inside modern CS orgs after scaling from CSM to leading a 100+ person team—and why most companies are still getting it wrong.

You’ll hear why “value” is still more storytelling than science, why health scores can’t be trusted, and why the future CSM won’t just manage customers… they’ll manage agents.

But here’s the twist: as AI automates more of the work, the human side of Customer Success is becoming even more critical. Monday.com is literally doubling down on time spent with customers—while everyone else is trying to scale it away.

Cassie also shares the bold bet they made: turning CSMs into revenue owners with variable comp—and why, in a consumption world, CS might actually be more commercial than sales.

---

Timestamps

0:00 - Preview & Introduction

1:10 - Cassie’s journey from being a CSM to RVP

4:15 - What’s changed in CS over the last 6 years

6:13 - Why measuring customer value is still broken

9:35 - Why monday.com doubled time with customers

12:37 - The rise of the “agent manager” CSM

14:07 - Scaling CS with AI vs human touch

16:47 - Why CSMs are more commercial than sales

18:10 - Challenges of shifting to revenue ownership

19:30 - Why CSMs should think commercially & not trust health scores

21:50 - Stop being a generalist: career advice

23:26 - AI fluency as the #1 priority for 2026

25:25 - Lightning round: F1, food, and fun

---

What You’ll Learn

* Why has no one cracked customer value measurement

* How to build value narratives that actually land with executives

* What AI should automate—and what should stay human

* Why the future CSM is an “agent manager”

* How monday.com is doubling customer time in an AI era

* Why CSMs should be more commercial than sales

* How to introduce variable comp for Customer Success

* Why health scores are not enough (and what to do instead)

---

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.

---

Where to Find Cassie Vaughn

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

---

Where to Find Josh:

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

Unchurned Substack: https://unchurned.substack.com/

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

Most companies treat AI rollouts like software deployments. But according to Christina Meng (OpenAI), AI adoption isn’t a technology problem — it’s a human transformation challenge.

In this episode of Unchurned, Josh Schachter sits down with Christina, the leader behind the OpenAI Champion Program, to explore how OpenAI empowers the people inside organizations who are driving AI adoption from within: champions.

Christina explains how OpenAI structures its champion ecosystem with executive champions, champion leads, and internal champions, and how these groups work together to drive real AI transformation across enterprise organizations.

She also shares how she built the OpenAI Champion Program from the ground up, why many companies struggle to sustain AI usage after the initial hype, and why customer success teams need to rethink how they measure adoption.

Finally, they discuss how champion communities can become one of the most powerful engines for product adoption, customer engagement, and long-term growth in SaaS.

---

Timestamps

0:00 - Preview & Introduction

1:30 - Meet Christina Meng (OpenAI)

3:05 - Christina’s Experience at Slack

4:50 - What a Champion Program actually is

7:27 - How Slack ran a 4,000-member champion community

10:00 - Who the champions are at Slack & OpenAI

11:40 - The 3 types of champions (executive, lead, internal)

12:50 - Executive champion engagement strategies

19:58 - How champion roundtables work

27:50 - What internal champions actually do

30:00 - Christina’s background and musical theatre

31:00 - A week in the life of a champion program leader

32:10 - Working with CS & product teams at OpenAI

34:20 - Measuring champion program success

37:20 - Why companies need customer education & champion programs

40:25 - How Christina uses AI and Codex in her workflow

---

What You’ll Learn

* What champion programs actually are and why they matter for SaaS companies

* The difference between customer advocates and customer champions

* How OpenAI structures its Champion Network across enterprise customers

* The 3 types of champions driving AI adoption in organizations

* Why AI adoption fails when treated as a simple tech rollout

* How companies are building internal AI champion networks

* How OpenAI gathers product feedback from champions

* How to measure activation and sustained product adoption

---

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.

---

Where to Find Christina Meng

LinkedIn: https://www.linkedin.com/in/christina-meng-78858725/

---

Where to Find Josh:

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

Unchurned Substack: https://unchurned.substack.com/

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

What does it actually take to move from human-first customer success to digital-first at scale?

In this episode of Unchurned, host Jenny Calvert sits down with Jo Massie, COO at Slido, to unpack how her team is transforming customer experience using AI, community-led support, and product-led growth.

Jo shares how Slido’s lean team manages marketing, customer success, and most of sales under one customer organization—and how aligning these functions unlocks faster execution, stronger feedback loops, and better customer outcomes.

They dive into how Slido is using AI chatbots to deflect 70% of support tickets, how their community became the center of their digital hub, and how experimentation and MVP thinking are key to surviving rapid AI innovation.

Jo also explains how Slido evolved after being acquired by Cisco, adapting from startup speed to enterprise scale while maintaining agility and experimentation.

If you're building digital-first customer success, PLG motions, or AI-enabled support, this episode is packed with practical insights.

---

Timestamps

0:00 - Preview & Introduction

0:41 - Meet Jo Massie & Jo's Role at Slido

2:21 - Breaking down silos with a digital team

4:00 - How AI chatbots reduced support escalations

5:48 - Using AI to scale the customer voice program

7:20 - Community-first support strategy

9:50 - Hiring for diversity of thinking vs specialization

11:30 - Slido’s acquisition by Cisco and the enterprise shift

13:05 - The pace of AI innovation and what excites Jo most

14:36 - Digital teams running weekly sprints for speed

16:43 - Advice for companies starting digital-first strategies

---

What You’ll Learn

* How Slido transitioned from human-first to digital-first customer success

* Why the community is becoming the new support channel

* How AI chatbots reduced support escalations to just 30% of tickets

* The role of AI in customer voice programs

* Lessons from scaling inside Cisco after Slido’s acquisition

---

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.

---

Where to Find Jo Massie

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

---

Where to Find Jenny:

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

---

Where to Find Josh:

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

Unchurned Substack: https://unchurned.substack.com/

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

Customer Success is changing fast, and many CS leaders are realizing that staying visible to customers between meetings is becoming essential.

In this episode of Unchurned, host Josh Schachter sits down with social selling expert Darren McKee to explore how LinkedIn can become a powerful engine for building relationships, staying top of mind with customers, and driving revenue growth.

Darren shares how he went from traditional sales to building a massive LinkedIn following through consistent posting and authentic storytelling — and how companies can turn employees into a distributed marketing and relationship engine.

The conversation dives into why CS leaders must become teachers in their industry, how social presence builds customer trust, and why authentic content often drives more business than traditional outreach.

If you're in Customer Success, Sales, or GTM leadership, this episode will give you a practical playbook for building relationships and staying relevant in an increasingly digital world.

---

Timestamps

0:00 - Preview & Introduction

1:23 - Meet Darren McKee

3:40 - Growing a LinkedIn audience through daily posting

7:00 - Why CS leaders should be active on LinkedIn

9:23 - Why human connection matters more than ever online

11:00 - How social selling drives real revenue (for startups & even billion-dollar companies)

16:00 - The 4 pillars of LinkedIn content (with examples)

28:21 - The Power of “Dwell Time”

29:30 - Authentic posts vs polished marketing posts

34:05 - Should employees be paid for posting on LinkedIn?

38:12 - The 5-3-1 LinkedIn engagement framework

---

What You’ll Learn

• Why Customer Success leaders should be active on LinkedIn

• How social visibility can help drive retention, expansion, and stronger relationships

• Why authentic storytelling outperforms polished marketing posts

• Darren McKee’s 5-3-1 daily engagement framework for building relationships on LinkedIn

• How companies can turn employees into a distributed marketing and relationship engine

• How to engage customers online between QBRs and formal meetings to stay relevant

---

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.

---

Where to Find Darren McKee

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

---

Where to Find Josh:

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

Unchurned Substack: https://unchurned.substack.com/

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

In this episode of Unchurned, Jenny Calvert sits down with Carsten Schütz, VP & Global Head of Scaled CS at SAP, to talk about how modern CS teams must evolve to serve thousands of customers without losing the human touch.

Carsten shares how his journey from startup CSM to SAP executive reshaped his thinking about scale, specialization, and the real role of AI in customer success.

The conversation dives deep into why the traditional “hire more CSMs” model doesn’t work anymore, how AI agents can support the long tail of customers, and why product usage data—not just sentiment—is the future of customer health.

One of the biggest takeaways: AI isn’t replacing customer success. It’s enabling teams to finally support the majority of customers who currently receive little to no human interaction.

---

Timestamps

0:00 - Preview & Introduction

0:55 - Meet Carsten Schütz

4:25 - The real answer to the generalist vs specialist debate

6:20 - What customers actually want from their CSMs

7:57 - What makes a truly valuable QBR

9:18 - Why AI is essential for the 80% of customers at scale

11:08 - The importance of keeping the human touch

12:02 - Using AI to drive adoption, detect risk, and churn prevention

13:55 - Why product usage data is critical for customer health

16:28 - What CS leaders should look for when hiring today

19:04 - How AI is changing how younger professionals work

20:55 - “This is the worst AI will ever be.”

21:48 - Q4 renewal strategy and human connection

23:33 - Why in-person conferences still matter

---

What You’ll Learn

* Why 80% of customers require a scalable CS strategy

* Why the generalist vs specialist debate is the wrong question

* How product usage data reveals hidden churn risks

* Why CS teams must think beyond 1-to-1 engagement

* How to scale digital engagement without losing human connection

* Why the future of CS is human-first, AI-powered

---

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.

---

Where to Find Carsten Schütz

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

---

Where to Find Jenny:

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

---

Where to Find Josh:

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

Unchurned Substack: https://unchurned.substack.com/

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

Customer Success doesn’t become mission-critical because you say it is.

It becomes mission-critical when it owns revenue.

In this episode of Unchurned, Josh Schachter sits down with Manish Chawla, CCO at PowerSchool, to talk about what it actually takes to make CS essential — to customers and to the company.

Manish doesn’t come from traditional CS. He’s been a CRO. A GM. He learned that the only truth that matters is what the customer believes.

Now he’s applying that lens to CS.

At PowerSchool, CSMs don’t just manage relationships. They carry GRR and expansion targets. AI isn’t a premium add-on — it’s table stakes. And cost-to-serve must go down while customer experience goes up.

This isn’t theory. It’s operational.

If Customer Success isn’t tied directly to profit, it risks becoming optional. And optional doesn’t survive.

This episode is for operators who want CS at the revenue table — not watching from the sidelines.

---

Timestamps

0:00 - Preview & Introduction

1:25 - Meet Manish Chawla & Overview of PowerSchool

3:35 - From consulting to CRO to CCO

6:13 - Why execution matters more than strategy

8:35 - Bringing a commercial mindset to Customer Success

10:52 - Should CSMs carry revenue? (GRR & expansion targets)

16:20 - Making CS mission-critical inside the company

17:42 - Cost-to-serve: Driving efficiency without hurting CX

18:50 - Scaling through digital CS. partner & ecosystems

21:25 - Designing CS for K-12 and vertical SaaS

28:30 - AI is table stakes (and customers won’t pay extra)

30:51 - Using AI internally to increase productivity

32:25 - Building a CS engineering team

35:45 - Becoming essential to customers

---

What You’ll Learn

* Why CSMs carry GRR and expansion targets — not just NPS

* Why AI is table stakes (and why customers won’t pay extra for it)

* How to lower cost-to-serve without lowering experience

* How to tie CS directly to the CEO’s revenue equation

* Why vertical SaaS demands deep domain fluency in CS hiring

* How to position the CSM as the COO to the AE’s CEO

---

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.

---

Where to Find the Guests

Manish's LinkedIn: https://www.linkedin.com/in/manishchawla1/

---

Where to Find Josh:

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

Unchurned Substack: https://unchurned.substack.com/

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

Is the future CSM a generalist empowered by specialist AI agents?

Live from Pulse Europe, Eleanora White, Global Head of CS & Solutions Architects at Supermetrics, joins Jenny Calvert to break down how her team is operationalizing Agentic AI inside customer success.

From internal AI agents that reduce friction…

To customer-facing automation at scale…

To autonomous agents that challenge and pressure-test insights…

Supermetrics is building a 3-phase AI roadmap that reshapes how CSMs work — without replacing the human relationship.

If you’re working on AI adoption or retention strategy — this episode is your blueprint.

---

Timestamps

0:00 - Preview & Introduction

0:40 - Meet Eleanora White

1:10 - AI as a Team Member

3:39 - Supermetrics’ 3-Phase AI Strategy

5:38 - Removing Friction with Internal AI

6:49 - The Future CSM Profile

9:00 - Hitting GRR Targets in Q4

11:03 - The “Stay-Alive” Retention Strategy

13:15 - Win-Back Metrics & LTV

14:27 - What’s Next for 2026

---

What You’ll Learn

* Why the best CSMs will become AI-powered generalists

* How to structure CS teams in the agentic era

* How Agentic AI can serve CSMs internally before customers

* The “stay-alive contract” retention strategy to increase long-term LTV

* How to win customers back without hurting GRR

* Why discovery is the most underrated CSM skill

---

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.

---

Where to Find the Guests

Eleanora's LinkedIn: https://www.linkedin.com/in/eleanora-white/

---

Where to Find Jenny:

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

---

Where to Find Josh:

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

Unchurned Substack: https://unchurned.substack.com/

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

Is community in B2B SaaS a cost center — or a growth engine hiding in plain sight?

In this episode of Unchurned, Josh Schachter sits down with Jon Wishart and community strategist Brian Oblinger to break down what community really means beyond vanity metrics and buzzwords.

They explore how community drives retention (GRR), expansion, and customer success — and why most companies are measuring it wrong. Plus, they unpack how AI is reshaping search, traffic, and discoverability, and why declining pageviews don’t mean declining value.

If you’re building, scaling, or rethinking your community strategy, this episode will change how you think about impact — and the future of customer connection.

---

Timestamps

0:00 - Preview & Introduction

1:45 - Meet Jon Wishart & Brian Oblinger

7:56 - What community in B2B SaaS actually is

9:00 - The “eras” of community ownership (Support → CS → Marketing → Product)

12:30 - Is community a cost center? And measuring impact

18:15 - The CFO conversation: investment vs expense

19:35 - AI, traffic declines, and community panic

21:30 - Why AI isn’t killing community

26:42 - The shift from “How do I?” to “How do we?”

30:40 - How community impacts feature development strategy

33:13 - Starting from zero: advice for new community builders

---

What You’ll Learn

* The core definition of community in B2B SaaS (without the fluff)

* How community drives retention, expansion, and lower support costs

* Why operational metrics (posts, members, pageviews) are outdated

* How to measure community’s business impact using cohort analysis

* What AI is really doing to search traffic and discoverability

* Why declining traffic doesn’t mean declining value

* How to future-proof your community strategy

* The fundamentals every new community leader must get right

---

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.

---

Where to Find the Guests

Brian's LinkedIn: https://www.linkedin.com/in/jon-wishart/

Jon's LinkedIn: https://www.linkedin.com/in/jon-wishart/

---

Where to Find Josh:

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

Unchurned Substack: https://unchurned.substack.com/

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

18 months ago, venture capitalist Brett Queener made a bold prediction: 75% of customer-facing software companies would disappear. Now he’s back—with receipts.

On this episode of Unchurned, Brett explains why traditional SaaS moats have collapsed, why “system of record” is no longer defensible, and why we’ve entered a new era of agentic software—where you don’t buy tools anymore… You hire them.

Brett introduces what he calls the Judgment Layer—the only remaining defensible advantage in AI-powered products. In a world where agents can build, code, write, and self-organize, your job shifts from operator to manager. And your product’s job shifts from workflow engine to embedded judgment engine.

If you build, invest in, or buy software, this episode is required listening.

---

Timestamps

0:00 - Preview & Introduction

2:15 - From GPT moment to Agents

4:02 - Survival in the AI era

6:50 - Meet Brett

8:00 - Why SaaS moats disappeared

10:40 - The Judgment Layer explained & Feedback loops

13:58 - Hiring software vs. buying software

---

What You’ll Learn

* Why most SaaS companies are now replaceable

* Why embedded judgment is more valuable than workflow automation

* The new decision framework for buy vs. build

* Why the humanities may outperform pure STEM in the AI era

* What founders must build to remain defensible

---

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.

---

Where to Find Brett Queener

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

Substack Article: https://queener.substack.com/p/in-the-end-it-may-just-be-judgement

Bonfire Ventures: https://www.bonfirevc.com/

---

Where to Find Josh:

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

Unchurned Substack: https://unchurned.substack.com/