[Un]Churned – The No. 1 Podcast for Customer Retention

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.

Watch Eric Gilpin, President of Go-To-Market at G2, reveal how he’s building the first-ever unified revenue org in a 210,000-product marketplace. In this episode, he takes us behind the scenes of G2’s “zero daylight” alignment strategy and how it led to a game-changing 31% YoY traffic spike. Discover why G2 made the controversial bet to let LLMs scrape their data (and why competitors are now paying the price), how to flip buyer intent into “churn intent” to catch customers before they leave, and how the difference between “freelancers” and “contractors” became worth $600M+ in revenue. This is marketplace strategy 101, told by someone who’s spent 25+ years perfecting it. Essential listening for GTM leaders, CS teams, and anyone building in B2B SaaS.

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Timestamps
0:00 - Preview & introduction
1:28 - Meet Eric Gilpin & overview of G2
6:50 - How Upwork scaled from $30M to $650M in gross sales volume
10:00 - Building G2’s first President of Go-To-Market role
11:13 - Zero daylight: Aligning marketing, BDRs, and all revenue teams
16:42 - Pivoting narrative from “SEO review site” to AEO visibility engine
18:15 - G2’s “Hunter Hunter” post-sales org (60% growth from expansion)
21:00 - The highest-value CS activities (hint: it’s not quarterly review sends)
23:23 - Self-serve + AI automation for the 150,000 SMB products
25:23 - The churn intent
27:28 - Why G2 allowed LLMs to train on their data
31:55 - Nostalgia and denial kill businesses

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What You’ll Learn
- How to eliminate silos by achieving “zero daylight” between marketing, sales, and revenue teams
- The whitespace model G2 uses to find expansion revenue
- How to build a “churn intent” system using buyer signals to catch churn before it happens
- Why allowing LLMs to scrape your data early creates a competitive moat
- The subtle power of reframing to unlock enterprise adoption and market perception
- Why is constantly challenging your own status quo the only defense against disruption

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

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Where to Find Eric Gilpin
LinkedIn: https://www.linkedin.com/in/ericgilpin/

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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.

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.

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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

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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

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

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Where to Find Ghazi Masood
LinkedIn: https://www.linkedin.com/in/ghazi-masood-09195a2/

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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.

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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

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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)

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

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Where to Find Cassie Vaughn
LinkedIn: https://www.linkedin.com/in/cassiebrown/

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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.

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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

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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

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

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Where to Find Christina Meng
LinkedIn: https://www.linkedin.com/in/christina-meng-78858725/

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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.

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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

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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

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

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Where to Find Jo Massie
LinkedIn: https://www.linkedin.com/in/jomassie/

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Where to Find Jenny:
LinkedIn: https://www.linkedin.com/in/jennycalvert/

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Where to Find Josh:
LinkedIn: https://www.linkedin.com/in/jschachter/
Unchurned Substack: https://unchurned.substack.com/