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

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

Most CS and sales teams have been told to "be more strategic." Few have been shown how.

Josh Schachter talks with customer discovery expert Bob London about what it actually takes to move a team above the line. Bob gets tactical fast: the inverted-pyramid structure that works for a 30-minute discovery call or a 5-minute QBR opener, the setup and board-level question that disarms and differentiates in the first few minutes, and the competitor question that CS leaders tell him is the best churn-risk signal they have.

He's also honest about the hard part. Methodologies don't adopt themselves, the ROI case rests on catching a handful of surprise churns, and behavior change only shows up if you track it: one-on-ones, keyword tracking, and AI scoring of real call transcripts before and after.

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What You'll Learn
- Why "be more strategic" is a directive without a path, and what to say to your team instead
- How to structure a conversation as an inverted pyramid
- Why "if your renewal were tomorrow, would you renew?" puts customers on the spot and gets you nothing
- The "head turner" follow-up that surfaces the gap between what customers have and what they're curious about
- How to spot the trigger words that make a question feel like it's about the customer's world
- What leaders have to do after the workshop for any of it to take hold
- A realistic way to think about ROI when the outcome is prevented surprise churn
- How AI call scoring can measure conversation quality before and after training

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Timestamps
0:00 - Preview & Intro
1:48 - Meet Bob London
2:28 - Why "be more strategic" is pressure with no path
5:18 - The mindset shift leaders have to make first
7:45 - The inverted pyramid and the board question that changes the conversation
14:52 - Forget "would you renew?" (ask this instead)
20:25 - Why customer-world trigger words work
22:18 - The board bullet point question
23:00 - How to measure ROI on better conversations
27:11 - Bob's path from fired CMO to 3,000 interviews

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Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com

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Where to Find the Guest
Bob London : https://www.linkedin.com/in/boblondon/
Website: https://www.boblondon.co/

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

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

The best executive roles are never posted, so how do you find them?

Andy Mowat, founder & CEO of Whispered and former exec at four unicorns, joins Josh Schachter to pull back the curtain on how senior go-to-market and CS leaders actually land their next role. After navigating between operating roles and founding companies himself, Andy built Whispered so top executives could share unposted roles and interview intel instead of competing in the dark. In this conversation, he shares the playbook. Whether you're quietly looking while in seat or actively on the market, this episode is a masterclass for job hunt.

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What You'll Learn
- Why 80%+ of VP and C-level roles are never posted publicly
- How VC/PE talent partners differ from executive recruiters, and how to get on their radar
- Why you should build relationships with people who already have the job you want
- Why role specificity beats being "open to any job"
- How to use target lists to unlock loose connections in your network
- Why backdooring to mid-level employees works (you don't need the hiring manager)
- How to treat your job search like an outbound sales funnel
- When comp and role level are actually negotiable
- Why thank-you notes still matter more than you think
- What's happening in the CS hiring market
- Why AI-native companies are heading into a churn wave
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Timestamps
0:00 - Preview & Intro
1:28 - Meet Andy Mowat (Founder, Whispered)
5:28 - How A+ candidates search differently
6:52 - Talent partners vs. recruiters and the 340-person Google group
10:15 - Career clarity, target lists & the power of loose connections
15:20 - Find & connect with the people who have the job you want
16:36 - Timing, recency bias, and building real relationships
18:50 - Why senior roles are never posted publicly
22:44 - Monitoring unposted roles with scrapers and AI
23:43 - Why the front door doesn't work
25:40 - No more referral fees
27:53 - Treat your job search like an outbound sales funnel
30:25 - Write thank-you notes
31:31 - The CS job market and the coming AI churn wave
33:03 - Comp negotiation and why half of all comp numbers are flexible
34:45 - Can you level up in this market?

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Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com

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Where to Find the Guest
Andy Mowat (Whispered): https://www.linkedin.com/in/amowat/
Whispered: https://www.whispered.com/

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

In this episode of the [Un]Churned Podcast, Josh Schachter sits down with Jake Saper, General Partner at Emergence Capital, to unpack the firm’s 25 year thesis of being “early experts in emerging business models,” from the on-prem-to-cloud shift that birthed their first investment in Salesforce, to vertical SaaS with Veeva, to what Jake calls AI-Native Services, or AINS.
They also dive into:
What “AI-Native Services” actually means, in Jake’s own words
The real story behind Gainsight’s shift from selling software to selling outcomes
Why the biggest headwind to this transformation is cultural, not technical
“Mirage product market fit,” the #1 mistake Jake sees in AI pitches right now
What Jake actually looks for in founders before he invests
Why tech vendors of the future might look more like insurance carriers than software companies

If you’re building anything in the AI services space, thinking about how AI changes SaaS margins, or just want to understand where venture capital thinks the next generational businesses will come from, this episode is a masterclass in spotting a category before it has a name.
Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at ⁠unchurned.substack.com.⁠
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Timestamps
00:00 – Intro & Backstory
01:37 – What Emergence Capital Focuses On, and How It Started
08:14 – Naming the Category: Why “AI-Native Services” (AINS)
12:42 – The Walk on the Embarcadero: How Gainsight’s Pivot Was Born
17:28 – The Biggest Headwind: It’s Cultural, Not Technical
20:24 – What Jake Looks For as an Investor: Domain Credibility
31:21 – The Hanover Park Story: 150 Fund CFOs
36:38 – Mirage Product Market Fit: The Overplayed Pattern in AINS Pitches
38:48 – The AINS Idea Jake Wants Someone to Build
42:07 – The Mafia, Dump Trucks, and Unexpected AI Competitors
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Where to Find Jake Saper:Jake's LinkedIn:  https://www.linkedin.com/in/jakesaper/
Emergence Capital: https://www.emcap.com/Where to Find Josh Schachter:Josh's LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com

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

What does it take to run 60% of a company?

Garrett Marker, Chief Revenue Officer at Brex, oversees about 700 people across sales, customer success, RevOps, partnerships, enablement, and support - and this year, his goal was to aggressively scale a sales team that industry data recently ranked the third-fastest growing in tech, without letting rep performance slip. It hasn't all gone to plan. Garrett is refreshingly candid with host Josh Schachter, grading the scaling effort a "B" - what held up, what broke, and how his team turned around a slumping segment in dramatic fashion. Along the way, he explains why the battle cards that used to last a quarter now go stale in about a week, why Brex bet on human SDRs while the market rushed toward AI ones, and why the hardest part of AI products isn't selling them at all.
It's a look inside the operating decisions of a CRO whose remit spans the entire customer lifecycle - from first touch through renewal and expansion.


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What You'll Learn
- How a struggling Brex segment did two months' worth of revenue in eight days and the AI-assisted diagnosis behind the course correction
- Why battle cards that used to last a quarter are now stale within about a week
- How AI role plays and automated call scoring turned weeks or months of rep ramp into hours or days
- Garrett's build-vs-buy rule
- What Brex's internally built "narrative platform" does that seller-productivity tools don't (mapping the full buyer's journey across sales, CS, and support)
- The question Garrett asked at the end of every demo as a seller and the rep whose career it transformed in three months
- How the TAP program works
- Why adoption, not sales, is the bottleneck for AI products
- How a shift in CS conversations (not product changes) grew book-closing adoption 20% in twelve months
- What Garrett believes it will take to increase NRR by 30 points in the next couple of years

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Timestamps
0:00 - Preview & Intro
1:52 - Meet Garrett Marker (CRO, Brex)
4:03 - Why founders buy like consumers
5:28 - Scaling the third-fastest-growing sales team in tech
7:28 - Solving today's AND tomorrow's problems
9:25 - 2 months of revenue in 8 days after a segment course correction
11:22 - How AI made competitive diagnosis faster
14:37 - Rebuilding enablement around AI and ramping reps in days
17:27 - How Brex decides build vs. buy
18:35 - Mapping the full buyer's journey across sales, CS, and support
21:38 - Success plans and buyer psychology
25:56 - Why won't you move forward?
27:53 - How SDRs earn on-the-spot promotions to AE
32:52 - Post-sale priorities: cracking AI product adoption at scale
35:11 - Why CS teams must understand the whole tech stack, not just their product (+20% book-closing adoption)

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Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com

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Where to Find the Guest
Garrett Marker: https://www.linkedin.com/in/gmarker/

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

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

Proofpoint had no named accounts. No digital motion. No success plans. Two years later, they've got an AI assistant wired into every customer's data, and an early warning system that catches churn risk a year out.
Mark Vovsi, Senior Director, CS Operations - GTM Automation & AI at Proofpoint went from building the CS foundation at Proofpoint to reinventing his own job around AL. This episode isn't a highlight reel. It's Mark walking through what actually got built, in what order, and why. In addition to the debate every CS leader is about to have about where AI-driven insights should even live.

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What You'll Learn
• Why Proofpoint's CS org started with zero named accounts and what it took to fix it
• The 4-stage AI maturity curve: generic AI → connected assistants → automation → predictive risk
• How role-based AI assistants get wired into customer 360 data (and why generic ChatGPT falls short)
• How Proofpoint auto-generates and auto-refreshes success plans for every customer, every quarter
• What an Al-powered early warning system for churn actually looks like under the hood
• The headless vs. cockpit debate: should CS insights live in the CSP, Slack/Teams, or Claude/MCP?
• Why data hygiene (not AI) is still the real blocker for most CS orgs
• How the CSM role is about to change: wider coverage ratios and "jack of all trades" expectations
• What Mark looks for when hiring for Al-era CS ops roles

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Timestamps
0:00 - Preview & Intro
2:00 - Meet Mark Vovsi (Proofpoint)
2:38 - Building CS from scratch at Proofpoint
3:52 - Overview of Proofpoint & It's CS org
5:28 - Fixing the data before fixing anything else
5:58 - What actually worked: top-down alignment + early adopters
6:28 - The shift to Al: from CS Ops to AI/GTM strategy
8:52 - Proofpoint's AI maturity model, stage by stage
9:30 - Role-based AI assistants wired into customer 360 data
10:50 - Auto-generating success plans at scale
13:50 - Building an early warning system for churn risk
15:00 - Headless AI vs. the CSP cockpit: where should insights live?
18:24 - The 12-month vision: catching risk a year out
20:00 - How the CSM role and CS hiring is about to change

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Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com

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Where to Find the Guest
Mark Vovsi: https://www.linkedin.com/in/vovsi/

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