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/

Six months in, Amanda Moran, is rebuilding customer success from scratch.

She spent eight years at LinkedIn mastering the old playbook: rules, workflows, perfectly timed emails. Now she's VP of Digital Customer Success at Darktrace, a cybersecurity company betting its future on securing AI itself.

But she's stuck on the question keeping every CS leader up at night. Autonomous agents aren't here. You can feel them coming. So what do you build right now, without wasting months on work the agents will replace?

Josh Schachter pushes into the hard parts: the data nobody connects, and why the next cybersecurity battle is the AI you're about to deploy.

This one's for anyone building toward a future that hasn't arrived.

---

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 rules-based outreach is on its way out, and what comes next

- How to build CS today without locking in throwaway automation

- The pooled support model behind 5 people serving 10,000 customers

- Why agentic AI is cybersecurity's next frontier

- The hidden signals in community and learning data

- What CS leaders are all quietly trying to figure out

---

Timestamps

0:00 - Preview & Introduction

1:42 - Meet Amanda Moran & Overview of Darktrace

3:00 - Transitioning from LinkedIn to cybersecurity

4:03 - Building AI-driven email engagement

6:50 - The Digital CS org at Darktrace

9:20 - The pooled model

11:39 - Renewals at Darktrace

12:45 - Securing AI itself: the July launch

14:17 - Internal AI enablement

15:17 - Building CS before the agents take over

17:50 - The data problem

20:10 - The in-between phase nobody has cracked

---

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

---

Where to Find the Guest

Amanda Moran: https://www.linkedin.com/in/amandammoran/

---

Where to Find Josh:

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

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

Most companies think of education as a support function, the real shift is treating it as a go-to-market engine.

In this episode of the UnChurned Podcast, Josh Schachter and Samantha Murray sit down with Yash Tekriwal, Head of Go-to-Market Engineering Ecosystem at Clay, to unpack how he became the company's first-ever GTM Engineer, why Clay rebranded its entire education team, and what it actually takes to build a learning ecosystem people don't just consume, but live inside of.

Yash shares the origin story of the GTM Engineer role, why he believes "education" has become a dirty word in tech, and how Clay is rethinking everything from LMS platforms to certification to attribution.

They also dive into:

- The origin story behind the first-ever "GTM Engineer" title

- Why Clay killed its education team and rebranded to a GTM engineering ecosystem

- Why traditional LMS platforms get learning fundamentally wrong

- The "control the environment, not the process" philosophy of learning

- Why brand affinity and "vibes" matter more than marketing attribution

- Rethinking certification and skill assessment in the age of AI

If you're building a GTM team, leading customer education, or trying to figure out how learning and community actually drive growth, this episode is a masterclass in building an ecosystem instead of a content library.

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

01:03 – Yash's Pre-Clay Career and Failed Startups

05:30 – Why He's More Of A Founder Than When He Was One

06:32 – Becoming Clay's First-Ever GTM Engineer

09:41 – Category Creation and Market Sizing

13:42 – "We Killed The Education Team At Clay"

15:36 – Why Education Became A Dirty Word In Tech

21:08 – Yash's Path From Teacher To GTM Engineer

24:54 – The Build vs. Buy Problem With LMS Platforms

28:09 – Control The Environment, Not The Process

32:37 – Why Attribution Doesn't Matter — It's All Vibes

36:18 – Inside Clay's Six-Pod GTM Ecosystem

42:16 – Yash's One-Year Goal: Rebuilding Certification

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

Where to Find the Guest:

Yash's LinkedIn: https://www.linkedin.com/in/yashtekriwal

Where to Find the Hosts:

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

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

Samantha's LinkedIn: https://www.linkedin.com/in/samantha-murray613/

Most founders treat product-market fit like a feeling. Mark Roberge thinks that's as absurd as calling profit a feeling.

The founding CRO of HubSpot, Harvard Business School lecturer, and Stage 2 Capital co-founder joins Josh to break down his new book, The Science of Scaling. The argument at the center of it - the decision of when and how fast to scale shouldn't be a gut call. It should be gated on retention.

Mark shares the leading indicator of retention (the one metric that predicts churn in a customer's first month), the 5-50-500 playbook a Microsoft leader used to launch new products, why Drift's founder flew across the country to onboard $50/month customers, and what "AI-native sales team" should actually mean in 2026 (with numbers attached).

If you work in Customer Success, this episode makes the case that you own the most strategic metric in the company. All proceeds from Mark's book go to McLean Hospital for mental health care.

---

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 we scale haphazardly, not scientifically

- A quantitative definition of product-market fit

- How to design a leading indicator of retention

- Real LIR examples from Slack, Harvey, Facebook, and Gainsight

- The three maturity levels of an LIR

- How a Microsoft leader used the 5-50-500 rep model to de-risk new product launches

- How to pick your threshold based on the blitzscale risk in your category

- Why product-market fit and go-to-market fit must be sequenced, not pursued at once

- How to know when to move past founder-led sales

- How to bring unit economics into board meetings

- Why blitzscaling fails more companies than it saves (and why VCs push it anyway)

- The two metrics that define an AI-native sales team in 2026

- Mark's four phases of the AI revolution in go-to-market

---

Timestamps

0:00 - Preview & Intro

1:30 - Meet Mark Roberge

3:07 - The Science of Scaling (All book proceeds go to McLean Hospital)

7:30 - We scale haphazardly, not scientifically

9:06 - Microsoft's 5-50-500 playbook

13:19 - Is product-market fit a feeling?

15:48 - The leading indicator of retention, explained

17:30 - Time to value vs. recurring value

19:42 - Designing your own LIR

24:04 - Why go-to-market fit comes after PMF

26:06 - Pitching this framework to VCs

28:15 - How to know when you have go-to-market fit

31:15 - Bringing the science to larger companies

33:00 - When to move beyond founder-led sales

35:51 - AI and the four phases of the GTM revolution

37:20 - What "AI-native sales team" means in 2026

---

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

---

Where to Find the Guest

Mark Roberge: https://www.linkedin.com/in/markroberge/

The Science of Scaling: https://a.co/d/0boDpDUc

Stage 2 Capital: https://www.stage2.capital/

---

Where to Find the Host:

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

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

Most leaders treat community as a marketing channel. They're leaving the real advantage on the table.

Chris Catania , Head of Community at Esri built community from a love of live music. Lately, he wrote the playbook. In this episode he joins Erica Kuhl, who scaled Salesforce's legendary Trailblazer community, and Josh Schachter to make the case that community isn't a nice-to-have. It's a strategic operating system competitors can't copy.

From Lego's near-bankruptcy turnaround to Marc Benioff, CEO of Salesforce, demanding harsher feedback, this episode reframes what community can do for a business.

---

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 community is a service to every team, not a marketing channel

- The importance of speaking each executive's language

- The "fake flowers vs real flowers" test for authentic community

- Why community-driven companies build an advantage rivals can't catch

- The three E's: enablement, experience, evaluation

- How to set a North Star while delivering ROI in small wins

---

Timestamps

0:00 - Preview & Intro

1:56 - Meet Chris Catania

6:27 - Three founders, one music origin story

10:17 - The Lego turnaround that saved the brand

14:25 - Fake flowers vs real flowers

17:28 - Why nobody likes the word "community"

22:05 - The Marc Benioff feedback story (CEO of Salesforce)

24:24 - Is Voice of the customer underleveraged?

31:47 - Erica ran Salesforce's first Twitter handle

33:22 - Community as a service and the unfair advantage

37:20 — One takeaway: the three E's

---

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

---

Where to Find the Guest

Chris Catania: https://www.linkedin.com/in/christophercatania/

Website: https://chriscatania.co/

---

Where to Find the Hosts:

Erica's LinkedIn: https://www.linkedin.com/in/ericakuhl

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

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

Everyone's racing to "do AI." Almost nobody can say what for.

Brian Evergreen, Forbes AI thought leader, author of Autonomous Transformation, ex-Microsoft, Founder & CEO of The Future Solving Company joins Josh Schachter to flip the playbook.

Start with a problem? That traps you in incrementalism.

Be data-driven? There's no data about the future.

The old industrial-era moves quietly sabotage every AI rollout.

Brian's fix: solve for a future you can feel. Then reverse-engineer it with one question: what would have to be true?

Inside: the reason-tree framework, the JFK moon test, and how to make renewal a panic-level no-brainer your champion fights for. You don't need the CEO's permission to start.

---

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 "start with a problem" caps your upside

- How "data-driven" quietly became unscientific

- Why green scorecards hide a shrinking business

- The JFK test for a visceral vision

- The reason-tree mapping "what would have to be true"

- Whether a revenue number can be a vision

- Helping customers build their own vision

- Starting all this without executive buy-in

---

Timestamps

0:00 - Preview & Introduction

2:00 - Meet Brian Evergreen (Ex-Microsoft)

4:30 - Why the digital-era playbook fails for AI

5:25 - "Start with a problem" is an incrementalism trap

6:00 - How "data-driven" turned unscientific

7:19 - All green scorecards but shrinking market share

8:40 - Netflix solved the same future twice

9:35 - No value vision? Don't invest in AI yet

12:40 - Getting over organizational inertia

15:30 - The reason-tree: "what would have to be true?"

18:25 - Can a vision be a number? (Replit's $1B ARR vision)

19:50 - Why most "strategy" is just a SWOT board

21:15 - You don't need the CEO's permission

---

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

---

Where to Find the Guest

Brian Evergreen: https://www.linkedin.com/in/brianevergreen/

Brian's Substack: https://newsletter.brianevergreen.com/

---

Where to Find Josh:

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

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

No one celebrates a new ERP. No champagne. Just groans.

Jean de Villiers, Chief Customer Officer at Unit4, wants to flip that script.

Jean shares they have kept customers for 20+ years in an industry built on dread. Secret? He runs customer success like a business, not a cost center. He cut the safe middle option. He's betting big on AI agents. And he trains his whole team to have the uncomfortable conversations most people avoid.

In this episode of Unchurned, Jean sits down with host Josh Schachter to unpack the playbook: why 45% of what customers pay for goes unused, how high-touch service drives a 50-point gap in customer promotion, and what it really takes to make people love the software they're supposed to hate.

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

---

What You'll Learn

- Why Unit4 runs CS as a profit center, not a cost

- How to hit 30% contribution margin to EBITDA in post-sales

- Why Unit4 cut mid-touch and kept only high and digital

- Packaging every service into a self-serve catalog

- Building an agentic digital CSM that feels high-touch

- The 50-point NPS gap between high-touch and self-serve

- Why 45% consumption is ERP's dirty secret

- Training non-sellers on the Challenger Sale method

- How AI plus human domain expertise wins together

---

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

---

Timestamps

0:00 - Preview and Introduction

1:44 - Meet Jean de Villiers

2:45 - What Unit4 does and its four verticals

4:32 - Customers who stay 20+ years

6:32 - The org structure of post-sales

7:32 - Running CS as a profit center under PE

8:50 - Why they cut mid-touch

9:45 - Packaging services into a catalog

12:20 - The agentic digital CSM vision

13:53 - Success For You: the high-touch subscription

18:12 - Sunsetting on-premise product, migrating to cloud & Ava

21:50 - The 45% consumption problem

23:57 - The 50-point NPS difference

25:30 - Challenger Sale training for everyone

31:40 - Wrap-up

---

Where to Find the Guest

Jean de Villiers (Unit4): https://www.linkedin.com/in/jeandevilliers/

---

Where to Find Josh:

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

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

Two hands. A free Slack channel. A spreadsheet. That was the entire toolkit when AWS asked Jason Dunn to build a developer community.

Jason Dunn spent five years on building something people actually want to belong to. He grew a developer community into thousands of members spread across more than a hundred countries, working with far less budget and tooling than you'd expect.

This conversation digs into what separates a living community from a glorified contact list. Why your earliest members carry so much weight. When to keep the door open and when to guard it. How to prove value when your best wins resist a dashboard. Why technical people walk the second something smells like a pitch. And how one small, slightly absurd reward became a badge people chased for months. A Real talk on getting people to show up for each other.

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

---

What You'll Learn

- Why the first members you pick set the tone forever

- The day-zero choice: community for everyone or for someone

- How to measure community when it's basically a vibe

- The trick to getting members to report their own wins

- Gamification with a lowercase G (and why it works)

- The golden jacket story and pent-up demand

- Why developers reject sales and marketing pipelines

- Scrappy tools beat fancy platforms every time

- The AI warning every new community manager needs

---

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

---

Timestamps

0:00 - Preview and Meet Jason Dunn

2:22 - What community meant at AWS in 2019

3:45 - The day-zero decision every builder faces

5:05 - From 200 invited seeds to 3,600 members

6:39 - Keeping the gates too open, too early

9:12 - Defining high-value member activity

11:23 - Measuring & reporting up: output, reach, and Dev.to

14:53 - The Content Reporting Tool (CRT)

16:02 - The real motivation behind self-reporting

18:24 - The Golden Jacket origin story & 130 jackets in one quarter

21:28 - The AWS Community toolkit

23:42 - Advice for new community managers

51:00 — Don't fall in love with the tools

53:00 — Humanity connecting with humanity

---

Where to Find the Guest

Jason Dunn: https://www.linkedin.com/in/jasonrobertdunn/

---

Where to Find Josh:

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

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