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.

---

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

---

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?

---

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

---

Where to Find the Guest

Andy Mowat (Whispered): https://www.linkedin.com/in/amowat/

Whispered: https://www.whispered.com/

---

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.⁠

--

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

--

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.

---

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

---

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)

---

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

---

Where to Find the Guest

Garrett Marker: https://www.linkedin.com/in/gmarker/

---

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.

---

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

---

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

---

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

---

Where to Find the Guest

Mark Vovsi: https://www.linkedin.com/in/vovsi/

---

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.

Simon Farthing, VP of Customer Success at Bloomreach, joins Josh Schachter to discuss what it actually takes to lead a customer success organization in the AI era. Drawing from his experience leading a 100-person CS and services team, Simon shares the lessons he's learned from experimenting with AI tools at scale, building internal tools, rethinking team structure, and preparing for what's next. It's a candid conversation about moving beyond AI hype and turning it into measurable operational impact.

---

What You'll Learn

- Lessons from testing 60+ AI tools across a 100-person CS organization

- How Simon built a personal AI command center in Claude

- A practical framework for build vs. buy vs. build-on-top decisions

- Why AI accuracy becomes non-negotiable at the executive level

- Why "tool migration" is becoming a core professional skill

- How Bloomreach rebalanced CSM compensation around GRR and NRR

- Why Forward Deployed Engineers are emerging and where they fit

---

Timestamps

0:00 - Preview & Intro

1:28 - Meet Simon Farthing, BloomReach overview

2:48 - 60+ AI tools tested, tool proliferation problem

6:00 - Building "Mission Control" in Claude

8:57 - Bottoms-up AI leadership structure

11:00 - The accuracy problem: when AI slides hit the boardroom

13:52 - Tool migration as a critical human skill

15:05 - Build vs. buy vs. build-on-top framework

17:00 - CSM comp redesign

18:33 - The rise of the Forward Deployed Engineer (FDE)

21:10 - Smaller customers and customer marketing, agentic AI

---

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

---

Where to Find the Guest

Simon Farthing: https://www.linkedin.com/in/simon-farthing/

---

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.

She went from treating eating disorders to running a $5M enterprise book at the biggest name in Customer Success and she didn't take no for an answer. Katy Bone, Enterprise CSM at Gainsight joins Josh to share the bathroom-humor pitch email that got her noticed, why vulnerability beats polish on LinkedIn, and the nonprofit born from unimaginable loss that's now reached families in 45 states.

Learn more or support the mission: https://www.blessingsforbarrett.com/

---

What You'll Learn

- How a therapy background translates directly into churn prevention and relationship-building

- The exact outreach tactics Katy used to break into a competitive CS hiring process with a non CS background

- Why vulnerable, human LinkedIn content builds deeper trust with enterprise stakeholders than polished thought-leadership

- How cross-functional collaboration skills transfer from healthcare advocacy to CS

- The story behind Blessings for Barrett and how it's scaled using AI tools

---

Timestamps

0:00 - Preview & Intro

0:48 - Meet Katy Bone, Enterprise CSM at Gainsight

1:27 - What an Enterprise CSM at GainSight actually does

2:15 - The Career Switch

5:02 - The parallel: fighting insurance denials vs. fighting churn

6:28 - Standing out against experienced CS candidates

7:47 - Sending a mock EBR prep before the interview

9:00 - The bathroom reading pitch email

10:28 - The LinkedIn banner that gets replies

12:02 - Learning it's okay to be vulnerable online

14:02 - What vulnerability has taught her about business

15:15 - Barrett's story & Blessings for Barrett

---

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

---

Where to Find the Guest

Katy Bone: https://www.linkedin.com/in/katy-bone-3b6334233/

---

Where to Find the Hosts:

Josh's LinkedIn: https://www.linkedin.com/in/jschachter/

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

AI adoption feels chaotic right now. Saumyo Mukherjee calls it "good chaos."

He's VP of Business Systems at Braze. 24-person team. Supports 2,000 employees. Sits between every GTM function using AI.

This episode covers vibe coding sprawl. Duplicate automations. And a handoff automation that replaced 1.5 days of manual work.

Plus his take on in-app intelligence, token budget and why tool-switching kills CSM productivity.

Real tactics from inside a fast-scaling SaaS company.

---

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

---

What you'll learn

- Why "good chaos" beats no chaos

- How Braze runs quarterly AI hackathons

- The sales-to-services handoff fix that saved days

- Why token costs are the new budget battle

- Why in-app intelligence beats tool-switching

---

Timestamps

0:00 - Preview & Introduction

1:30 - Meet Saumyo Mukherjee, VP of Business Systems at Braze

3:52 - Vibe coding sprawl problem

7:53 - The AI idea box & Sales-to-services handoff fix

11:52 - Balancing freedom and guardrails (Quarterly AI hackathons)

14:32 - Anthropic, token costs, and budget strategy

18:30 - Why in-app intelligence wins

19:45 - Braze's return to Gainsight

---

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

---

Where to Find the Guest

Saumyo Mukherjee: https://www.linkedin.com/in/saumyo/

---

Where to Find Josh:

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

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

Most companies think they're ahead on AI. The data says otherwise. Even the most sophisticated firms are only about 5% of the way down the journey.

In this episode of the [Un]Churned Podcast, Josh Schachter sits down with Matthew Kropp, Managing Director, Senior Partner, and Chief AI Officer at BCG, who's advised roughly 400 companies' boards and executive teams on AI strategy since ChatGPT launched. They unpack why most AI adoption stalls out at "1,000 chatbots and no value," the real psychological reasons people resist using these tools, and why the smartest company isn't the one winning anymore, it's the one using AI the most.

Matthew also opens up about Jessica, his personal experiment building a fully AI-run company, no human employees, agents making the decisions, himself acting only as "the governor."

They also dive into:

- Why 80% of engineers use AI tools, but only 5% actually use them to write code

- The four real reasons people don't adopt AI, and why "identity threat" is the biggest one

- Why using AI more, and more productively, is becoming the new competitive edge

- Why AI-native companies have a growing allergy to middle management

- Whether consulting itself is under threat, and why demand for advice isn't going anywhere while the work itself changes

If you're leading AI adoption inside your company, worried about what AI means for your role, or just want a clear-eyed look at what's actually working right now, this episode is worth your full attention.

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

Chapters

00:00 – Intro & Backstory

03:33 – Biggest Shifts In How Executives Think About AI

08:32 – The Four Reasons Companies Don't Adopt AI

16:20 – Marketing, Sales & Insurance's AI Transformation

18:59 – Token-Based Competition & "Token Maxing"

23:28 – Inside BCG's 3,000-Person Engineering Org

28:42 – AI Brain Fry: The Psychological Cost

30:59 – What Happens To Middle Management

33:17 – Is Consulting Under Threat?

39:21 – Building Jessica: A Zero-Human Company

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

Where to Find the Guest:

Matthew's Linkedin : https://www.linkedin.com/in/matt-kropp/

Where to Find the Host:

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.

He built the dashboards. Now he's questioning if they'll even exist in two years.

Ziv Peled just added "Chief AI Officer" on top of Chief Customer Officer to his title at AppsFlyer. In this episode, he breaks down what that actually means: not a figurehead role, but hands-on rebuilding of workflows, architecture decisions, and the mindset of an entire org. Josh and Ziv chat about how AppsFlyer built their own $20/month AI pipeline on top of Gong instead of replacing it, why "build vs. buy" isn't the binary everyone thinks, what happens to your AI costs, and why "50x ROI" claims are mostly noise; plus the line that stopped the whole conversation: "When is the last dashboard?"

---

What You'll Learn

- What a Chief AI Officer actually does day-to-day

- Why AppsFlyer upsold into Gong instead of churning

- Why most AI ROI metrics ("10x, 50x") don't hold up

- What's changing with AI vendor pricing/consumption limits

- How to think about AI security risk without a rulebook to follow yet

---

Timestamps

0:00 - Preview & Intro

1:30 - Meet Ziv Peled, CAIO at AppsFlyer

4:40 - How the CAIO role came to be

6:50 - Build vs. buy: Salesforce, Gong, and AppsFlyer's own MCP

9:25 - Why AppsFlyer isn't churning off Gong (they upsold)

12:20 - What is Mythos? (and the quantum computing tangent)

13:50 - The 90-minute video, 2-minute AI analysis story

14:42 - How AI is changing competitive advantage

16:10 - What it actually takes to become an AI-native company

19:33 - Rapid fire: adoption, measurement, expense, security

---

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

---

Where to Find the Guest

Ziv Peled: https://www.linkedin.com/in/zivpeled

---

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.

Deltek's CCO Margo Martin and newly-appointed VP Customer Strategy & Services at Deltek Jason Goldsmith reveal how Claude turned three siloed post-sale teams into one AI-first machine and why they built a brand new executive role just to keep up.

Deltek didn't just adopt AI. They restructured around it. After Claude and Claude Code cut documentation timelines by 80% and dev cycles by 50-60%, CCO Margo Martin realized her three post-sale orgs (implementation, CS, and support) were quietly duplicating AI work. Her fix? A brand-new "AI convergence" role . And she picked an internal boomerang employee to run it.

In this episode, you'll hear exactly how they built the business case, picked the right leader, and what's next on the roadmap.

---

What You'll Learn

- The tradeoff between touchless implementation and long-term customer stickiness

- How Claude Code cut custom implementation timelines by 50-60%

- Why Deltek reduced customer documentation & training time by 80%

- How to spot "AI silos" forming across your org before they cost you

- What it takes to build (and pitch) a brand-new AI strategy role internally

- Deltek's build-vs-buy framework for AI tools

- How CX leaders are using personal AI "chiefs of staff" day-to-day

- Why Deltek is rebuilding its entire customer journey around AI

- How to balance automation speed with customer stickiness

---

Timestamps

0:00 - Preview & Intro

1:50 - Meet Margo Martin & Jason Goldsmith (Deltek)

2:45 - What Deltek does & org structure

6:40 - How Claude Code changed everything

10:23 - Duplicate AI efforts & the new VP of AI strategy role

14:45 - Why Jason was the pick

19:10 - Jason's 30/60/90 day plan

24:10 - Predicting the first team to join Jason's org

26:45 - Personal AI chiefs of staff

28:28 - Build vs. buy: Deltek's AI tooling philosophy

32:56 - KPIs and metrics for AI transformation

---

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

---

Where to Find the Guest

Margo Martin: https://www.linkedin.com/in/margomartin-/

Jason Goldsmith: https://www.linkedin.com/in/jwgoldsmith/

---

Where to Find the Hosts:

Josh's LinkedIn: https://www.linkedin.com/in/jschachter/

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