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Customer success is changing fast, and the CSMs who thrive will be the ones who speak the language of revenue. In this episode of Unchurned, Josh Schachter sits down in New York with Jon Johnson, former co-host of [Un]churned & Strategic Principal Customer Success Manager at Gainsight, who manages some of the largest global accounts in the industry. Jon shares how he keeps multinational stakeholders aligned, why empathy still matters at the executive level, and why he thinks CSMs need to take ownership of commercial outcomes before the job forces the issue. They also debate whether SaaS will go “headless” in the next 18 months and how AI has changed Jon’s workload and anxiety. The conversation ends with Jon reading from his poetry collection Caterwaul and a lightning round. Timestamps 0:00 - Preview & Intro 0:57 - Jon Johnson returns to [Un]churned & the banter 2:35 - What Jon does at Gainsight 4:55 - Practising empathy and making customers feel valued 9:00 - Josh makes a surprise announcement 9:51 - 15 years in CS: from startups to global enterprise 11:00 - How customer success changes when you're managing thousands of users 13:00 - Why CSMs are moving closer to the executive level 16:30 - The three pillars: commercial, strategic, technical 18:38 - Why CSMs need commercial accountability 23:23 - Will B2B SaaS become headless in the next 18 months? 27:21 - AI, anxiety, and staying proactive 31:42 - Caterwaul: turning anxiety into art 34:28 - Jon reads “Holy Hands” 36:00 - Deconstructing faith and holiness 38:30 - Lightning round What You'll Learn - How AI is pushing CSMs toward more strategic, executive-level work - Why being proactive about AI reduces AI anxiety - Why CSMs should build commercial skills now, before they’re forced to - How to reframe “value” so CSMs can tell the story of their impact - Why enterprise SaaS adoption will move differently from SMB and mid-market - How consumption and outcome-based pricing can give CS a real seat at the table - Whether SaaS will really go headless, and what that means for CS teams --- Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com --- Where to Find the Guest Jon Johnson: https://www.linkedin.com/in/jonwilliamjohnson/ Jon's Music - Wild Coast: https://open.spotify.com/artist/17TwPEUjOWx4BESKVsqrPK?si=8DjlJdq0SWePHS5r-v1FGQ Jon on Substack: https://jonwilliamjohnson.com/ --- Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/ Unchurned Substack: https://unchurned.substack.com/

Is AI still an experiment on your customer success team, or is it delivering results? In this episode of Unchurned, Rod Cherkas, CEO of HelloCCO and author of The Chief Customer Officer Playbook for the AI Era, joins Josh Schachter to talk about what post-sale leaders need to do now. Rod shares findings from his research with nearly 200 post-sale leaders, explains why CFOs are asking for proof of AI's impact, and gives a practical path from scattered pilots to measurable results. The conversation covers governance, change management, and the leadership habits that make AI stick, along with a real example of AI automating a painful handoff process. If you're planning for 2027, this episode gives you a clear way to think about it. What you'll learn - How to connect AI initiatives to the metrics your CFO cares about - Why leader adoption matters more than tool rollouts, and how to model AI use for your team - How to pick 4–5 key metrics and align AI pilots around one or two of them - A simple way to start with a company-grounded AI assistant, without overbuilding the knowledge base - When to buy enterprise AI tools and when (and when not) to build on top of them - How to assign an AI champion on your team and create a practical rollout structure - What the future of customer success roles may look like, and which skills will matter most Timestamps 0:00 - Preview 1:10 - Introduction & Meet Rod Cherkas 3:15 - Why CFOs want measurable AI results 5:20 - Rolling out AI with governance and expectations 6:28 - Why leaders are resisting change 10:20 - Lessons from his time at Marketo for the AI era 12:38 - Frontline innovators who are ahead of the curve 13:45 - Focusing on continous L & D 15:10 - Automating the sales handoff 17:30 - Starting simple with a company-grounded AI assistant 20:10 - Measuring AI impact with key metrics 22:28 - Why change management takes longer than expected 23:37 - Delegating AI vs. leading it yourself 27:35 - Role modeling and making AI part of daily work 30:15 - Build vs. buy: what to build and what to avoid 33:35 - The future of customer success --- Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com --- Where to Find the Guest Rod Cherkas: https://www.linkedin.com/in/rodcherkas/ --- Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/ Unchurned Substack: https://unchurned.substack.com/

Most companies treat renewals as a sales function. The real shift is treating retention as a job for the whole company. In this episode of the [Un]Churned Podcast, Josh Schachter sits down with Mike Marguglio, EVP of Global Renewals at Salesforce, to unpack how his team manages almost 400,000 renewals a year, how Salesforce brought attrition from over 20% to about 8%, and what AI agents are actually doing in renewals today. Mike shares how a renewals agent turned hours of contract research into an executive view, what hasn’t worked with AI, and how the shift from licenses to consumption is changing the renewal playbook. They also dive into: - How the attrition council aligns senior leaders across the company on retention - Why “a dollar of existing business is just as important as a dollar new business” - How a renewals agent, Ask Renewals, and a long-tail agent are changing the job - What hasn’t worked with AI: incomplete summaries, distrust, and low adoption - How pricing is shifting from licenses to consumption and human-plus-agent models - Why Mike wants renewal to be “a non-event” If you’re leading renewals, building a customer success team, or trying to figure out how AI agents fit into retention, this episode shows how Salesforce runs renewals at scale. Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com. Chapters 00:00 – Intro & Salesforce Renewals at Scale 01:36 – Why 400,000 Renewals Is So Complex 05:03 – The Attrition Council: From Over 20% to About 8% 09:42 – What the Renewals Team Is Doing With AI 17:09 – What AI Caught That Humans Missed 20:28 – How Pricing Changes the Renewal Playbook 22:06 – What Hasn’t Worked With AI 26:05 – AI Adoption and the One-Year Forecast 29:00 – Automating the Long Tail 35:27 – Advice for People Starting Out in Renewals Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com Where to Find the Guest: Mike’s LinkedIn: https://www.linkedin.com/in/michael-marguglio-209895/ 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. Can a nine-year-old SaaS company reinvent itself as an AI-native services business before the market leaves it behind? On this episode of Unchurned, Josh Schachter, SVP of Strategy and Go-to-Market Development at Gainsight, sits down with AJ Bruno, Co-Founder and CEO of QuotaPath. AJ started QuotaPath after years of reps asking why they couldn't get paid correctly. Today the company serves more than 1,000 customers and over 50,000 reps. Now it's making its biggest bet yet: running commissions for customers instead of selling them software seats, and eventually pricing on outcomes like improved GRR and lower cost of sale. AJ and Josh compare notes on how Gainsight and QuotaPath are both moving to AI-native services. They discuss why trust is the real barrier, how to prove causality when many factors drive revenue, why buyers resist outcome-based pricing, and what it's like to build a startup inside your own startup while still hitting plan for the board. AJ is candid about the stakes: if QuotaPath doesn't make this move, it becomes another forgotten SaaS tool. --- What You'll Learn - Why so many companies deliberately keep comp plans confusing, and what that costs them - Why product-led growth failed for a sensitive category like commissions - How QuotaPath is moving from seat-based SaaS to AI-native services - What "selling outcomes" actually means, and how incentives can move metrics like GRR - Why outcome-based pricing is a hard sell, and how a crawl-walk-run approach reduces risk - How Gainsight is applying the same model to end-to-end renewals - What it takes to rediscover product-market fit inside a mature company --- Timestamps 0:00 - Preview & Meet AJ Bruno 3:35 - What is QuotaPath? The compensation & commissions problem 5:15 - Why companies keep comp plans confusing 6:20 - Why product-led growth didn't work for comp 8:20 - 10 years in: founder envy and wild pivots 10:34 - The return of hustle culture and in-office startups 13:00 - The pivot: from SaaS seats to AI-native services 16:48 - Selling outcomes: incentives that move GRR 19:19 - What QuotaPath actually runs for customers 21:53 - Why nobody wants to pay for outcomes 23:20 - Building a startup within a startup 25:15 - AI-native services unite --- Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com --- Where to Find the Guest AJ Bruno: https://www.linkedin.com/in/ajbruno3/ --- 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 future of customer renewals is here. And it's AI-native. Josh Schachter sits down with Grant Clarke, EVP & GM of Gainsight Atlas, to explore how AI agents combined with human renewal managers are transforming the renewal landscape. Grant, a 15-year veteran of renewal operations at ServiceSource, explains how Atlas manages entire renewal books through an outcome-based model—not software licensing. Discover why deploying AI agents in renewals is harder than it looks, how Gainsight is pioneering a new category called AI Native Services (AINS), and why the long tail of customers just became manageable. Plus: the surprising story behind Grant's 15 beehives outside Nashville. --- What You'll Learn - How AI agents are transforming customer renewals at scale - Why deploying AI agents in renewals is fundamentally hard - The margin economics that make productizing AI agents profitable - Why the long tail of customers is now economically viable to serve - How combining AI + human renewal managers creates better customer outcomes --- Timestamps 0:00 - Preview & Meet Grant Clarke 2:00 - What is Atlas? 4:50 - Grant's Background: ServiceSource & Dropbox 11:05 - How Atlas onboards a new customer 13:04 - Data hygiene: "The D word" 14:21 - The ideal customer profile for Atlas 16:20 A day in the life: the Atlas cockpit 17:55 - When the agent hands off to a human 19:05 - The learning loop: forward deployed engineers & 2-week sprints 20:10 - The business model: avoiding the pure-services trap 22:04 - Mirage PMF: go fast, go slow, go fast again 23:35 - What's next for Atlas: Agentic judgment and renewal edge cases 26:40 - Can AINS hit 70% gross margins? 26:35 The renewal action inventory: 10–25 actions per renewal 28:38 From 20% to 55% agent-led actions: margin accretion 29:43 Grant's 15 beehives outside Nashville 32:39 Wrap-up --- Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com --- Where to Find the Guest Grant Clarke: https://www.linkedin.com/in/grantclarke/ --- Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/ Unchurned Substack: https://unchurned.substack.com/

Most companies think of customer success as a support function that ships software. The real shift is treating it as a co-build practice that ships outcomes. In this episode of the [Un]Churned Podcast, Josh Schachter sits down with Christina Parra, Ariel Risman, and Kellie Woodin, three members of Notion's Outcomes Architecture team, to unpack how Notion rebuilt its entire customer success motion around AI, workshops, and shared commercial ownership. Christina, Ariel, and Kellie share how their roles evolved from traditional CSM to "Outcomes Architect," why they stopped selling software and started selling work, and how an AI maturity model now shapes everything from onboarding workshops to renewal conversations. They also dive into: The shift from customer success manager to outcomes architect and what it actually means to "co-build" with a customer How workshops (some with 180+ attendees) replace one-to-many trainings Proving ROI in a consumption-based pricing model, credit by credit Why CS teams are absorbing commercial ownership and what that's taught them about creative expansion levers Notion's internal multi-agent feature-request pipeline, and why they see AI as abundance, not scarcity If you're rethinking what customer success looks like in an agentic AI world, or figuring out how to prove ROI on usage-based pricing, this episode is a blueprint for turning your CS team into co-build architects. Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com. Chapters 00:00 – Intro & Guest Backgrounds 01:36 – What Is Notion? 04:25 – From Customer Success to Outcomes Architecture 08:51 – Ariel's Book: Deep Discovery & the Workshop Format 15:10 – The AI Maturity Model 21:37 – From Success Plans to AI Transformation Plans 23:14 – Benchmarking, ROI & Proving Value in Consumption-Based Pricing 28:01 – Becoming Strategic Partners: CS Owns Commercials 32:50 – Lessons From Owning Renewals & Hiring for Curiosity 37:30 – The Feature Request Pipeline & AI as Abundance Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com Where to Find the Guests: Christina Parra's LinkedIn: https://www.linkedin.com/in/christina-wills/ Ariel Risman's LinkedIn: https://www.linkedin.com/in/ariel-risman/ Kellie Woodin's LinkedIn: https://www.linkedin.com/in/kelliewoodin/ Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/ [Un]churned 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. Rebecca Nerad, VP of Customer Success at Advantive, owns retention across four lines of business built from 17 acquisitions in four years. She joins Josh to break down what post-merger integration looks like from the post-sales seat:sitting in on diligence before deals close, inheriting handshake contracts nobody documented, and owning the renewal number for customers she's only just met. Plus the objection-handling agent she built on months of renewal desk recordings, and her candid take on why she still can't measure what it's worth. --- What You'll Learn - How to structure a CS org that spans across multiple lines of business - How to not lose customer knowledge from acquired companies - Hiring & coaching for empathy - The internal objection-handling agent built from renewal negotiation history - Why time to response may be the retention metric AI actually moves - The customization trap AI reintroduces --- Timestamps 0:00 - Preview & Intro 0:58 - Meet Rebecca Nerad (VP of CS, Advantive) 1:22 - 17 acquisitions in four years 3:52 - Playbook for post-merger customer success 5:12 - Handshake deals and undocumented contracts 6:51 - What acquired companies do better 7:46 - Running CS post-sales motion 11:15 - Staffing CSMs by industry, not product 13:41 - Hiring for curiosity and EQ 14:28 - How you actually coach empathy 17:48 - Taking an agentic AI course as a VP 18:55 - Building an objection-handling agent 22:05 - The AI measurement problem 24:00 - Time to response as the real lever 25:32 - At-risk tickets, save plays, and QBRs 28:24 - Grading the long-tail segment 29:19 - AI adoption as the CS opportunity 30:23 - The dashboard-at-scale trap --- Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com --- Where to Find the Guest Rebecca Nerad (Advantive): https://www.linkedin.com/in/rebeccanerad --- 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. 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. --- 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 --- 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 --- Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com --- Where to Find the Guest Bob London : https://www.linkedin.com/in/boblondon/ Website: https://www.boblondon.co/ --- 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. --- 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 wordsThe real story behind Gainsight’s shift from selling software to selling outcomesWhy the biggest headwind to this transformation is cultural, not technical“Mirage product market fit,” the #1 mistake Jake sees in AI pitches right nowWhat Jake actually looks for in founders before he investsWhy 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/