Why CSMs Need Equanimity, Not Positivity ft. Kevin Bailey (Dreamfuel)

Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.Your customer says they’re not renewing. Your heart races, you stop breathing, and the only thing you want is to get off the call. Kevin Bailey, co-founder & CEO of Dreamfuel and a mental performance coach with a master’s in applied neuroscience, says that reaction is physiology, not personality, and that it can be trained.Kevin brings the playbook used by pro athletes and military operators to post-sales leaders. He explains why AI is making leadership more mentally draining by stripping out calm, low-effort work and leaving a day full of rapid, high-stakes decisions. He maps the four states your nervous system cycles through, shows how fight, flight and freeze responses quietly make your decisions for you, and explains why equanimity is the state top performers from Michael Jordan to Navy SEALs train for.Then it gets practical: a 30-breath reset you can do before a tough QBR, how to stay steady during a churn conversation, a one-line reframe that keeps you composed, and the morning rehearsal journaling method Kevin credits with raising his close rate. He also shares the story of losing his biggest customer and why it became the turning point for his company.---What You'll Learn- Why AI is increasing decision fatigue and mental exhaustion for CS and post-sales leaders, not reducing it- The four nervous-system states and how to recognize which one you’re in during a meeting- How a flight response in a tough QBR can lower your thinking power and drain your energy- The 30-breath reset and box breathing techniques for getting centered before high-stakes calls- How to stay calm and compassionate when a customer tells you they’re churning- The “best thing that could have happened” reframe and why it works without being self-deception- How rehearsal journaling uses visualization to shape how you show up each day- How losing a top customer can become a growth catalyst---Timestamps0:00 - Preview & Meet Kevin Bailey1:22 - Overview of DreamFuel3:55 - Kevin’s freeze response at his first startup7:32 - The Greenlight Guru turnaround and a 20% close-rate lift8:39 - The founder roller coaster and equanimity10:47 - Michael Jordan, Tim Grover and the flu game13:00 - How AI is causing decision fatigue15:36 - The science: four nervous-system states17:24 - Flight response in a tough QBR20:20 - Freeze, fawn and focus21:32 - Why equanimity beats every other state23:12 - The 30-breath reset and box breathing25:14 - How long the effect lasts26:18 - Don’t stop breathing on a churn call28:03 - The “best thing that could have happened” reframe29:44 - Does your subconscious buy it?32:35 - Holding form under pressure33:20 - Post-it notes as mindset cues34:30 - How stress affects memory36:57 - Reframing isn’t lying to yourself37:32 - When your biggest customer churns39:43 - Neuroplasticity and rewiring beliefs42:31 - Rehearsal journaling45:17 - Feel it, then use music to amplify it---Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com---Where to Find the GuestKevin Bailey: https://www.linkedin.com/in/kevinjamesbailey/---Where to Find the Hosts: Josh's LinkedIn: https://www.linkedin.com/in/jschachter/Unchurned Substack: https://unchurned.substack.com/

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.Timestamps0:00 - Preview & Intro0:57 - Jon Johnson returns to [Un]churned & the banter2:35 - What Jon does at Gainsight4:55 - Practising empathy and making customers feel valued 9:00 - Josh makes a surprise announcement9:51 - 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, technical18:38 - Why CSMs need commercial accountability 23:23 - Will B2B SaaS become headless in the next 18 months? 27:21 - AI, anxiety, and staying proactive31:42 - Caterwaul: turning anxiety into art 34:28 - Jon reads “Holy Hands” 36:00 - Deconstructing faith and holiness38:30 - Lightning roundWhat 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 GuestJon Johnson: https://www.linkedin.com/in/jonwilliamjohnson/Jon's Music - Wild Coast: https://open.spotify.com/artist/17TwPEUjOWx4BESKVsqrPK?si=8DjlJdq0SWePHS5r-v1FGQJon 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 mostTimestamps0:00 - Preview 1:10 - Introduction & Meet Rod Cherkas3:15 - Why CFOs want measurable AI results5:20 - Rolling out AI with governance and expectations6:28 - Why leaders are resisting change10:20 - Lessons from his time at Marketo for the AI era12:38 - Frontline innovators who are ahead of the curve13:45 - Focusing on continous L & D15:10 - Automating the sales handoff17:30 - Starting simple with a company-grounded AI assistant20:10 - Measuring AI impact with key metrics22:28 - Why change management takes longer than expected23:37 - Delegating AI vs. leading it yourself27:35 - Role modeling and making AI part of daily work30:15 - Build vs. buy: what to build and what to avoid33:35 - 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 GuestRod 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.Chapters00:00 – Intro & Salesforce Renewals at Scale01:36 – Why 400,000 Renewals Is So Complex05:03 – The Attrition Council: From Over 20% to About 8%09:42 – What the Renewals Team Is Doing With AI17:09 – What AI Caught That Humans Missed20:28 – How Pricing Changes the Renewal Playbook22:06 – What Hasn’t Worked With AI26:05 – AI Adoption and the One-Year Forecast29:00 – Automating the Long Tail35:27 – Advice for People Starting Out in RenewalsJosh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.comWhere 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---Timestamps0:00 - Preview & Meet AJ Bruno3:35 - What is QuotaPath? The compensation & commissions problem5:15 - Why companies keep comp plans confusing6:20 - Why product-led growth didn't work for comp8:20 - 10 years in: founder envy and wild pivots10:34 - The return of hustle culture and in-office startups13:00 - The pivot: from SaaS seats to AI-native services16:48 - Selling outcomes: incentives that move GRR19:19 - What QuotaPath actually runs for customers21:53 - Why nobody wants to pay for outcomes23:20 - Building a startup within a startup25:15 - 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 GuestAJ 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---Timestamps0:00 - Preview & Meet Grant Clarke2:00 - What is Atlas?4:50 - Grant's Background: ServiceSource & Dropbox11:05 - How Atlas onboards a new customer13:04 - Data hygiene: "The D word"14:21 - The ideal customer profile for Atlas16:20 A day in the life: the Atlas cockpit17:55 - When the agent hands off to a human19:05 - The learning loop: forward deployed engineers & 2-week sprints20:10 - The business model: avoiding the pure-services trap22:04 - Mirage PMF: go fast, go slow, go fast again23:35 - What's next for Atlas: Agentic judgment and renewal edge cases26:40 - Can AINS hit 70% gross margins?26:35 The renewal action inventory: 10–25 actions per renewal28:38 From 20% to 55% agent-led actions: margin accretion29:43 Grant's 15 beehives outside Nashville32:39 Wrap-up---Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com---Where to Find the GuestGrant 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 customerHow workshops (some with 180+ attendees) replace one-to-many trainingsProving ROI in a consumption-based pricing model, credit by creditWhy CS teams are absorbing commercial ownership and what that's taught them about creative expansion leversNotion's internal multi-agent feature-request pipeline, and why they see AI as abundance, not scarcityIf 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.Chapters00:00 – Intro & Guest Backgrounds01:36 – What Is Notion?04:25 – From Customer Success to Outcomes Architecture08:51 – Ariel's Book: Deep Discovery & the Workshop Format15:10 – The AI Maturity Model21:37 – From Success Plans to AI Transformation Plans23:14 – Benchmarking, ROI & Proving Value in Consumption-Based Pricing28:01 – Becoming Strategic Partners: CS Owns Commercials32:50 – Lessons From Owning Renewals & Hiring for Curiosity37:30 – The Feature Request Pipeline & AI as AbundanceJosh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.comWhere 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---Timestamps0:00 - Preview & Intro0:58 - Meet Rebecca Nerad (VP of CS, Advantive)1:22 - 17 acquisitions in four years3:52 - Playbook for post-merger customer success5:12 - Handshake deals and undocumented contracts6:51 - What acquired companies do better7:46 - Running CS post-sales motion 11:15 - Staffing CSMs by industry, not product13:41 - Hiring for curiosity and EQ 14:28 - How you actually coach empathy17:48 - Taking an agentic AI course as a VP18:55 - Building an objection-handling agent22:05 - The AI measurement problem24:00 - Time to response as the real lever25:32 - At-risk tickets, save plays, and QBRs28:24 - Grading the long-tail segment29:19 - AI adoption as the CS opportunity30:23 - 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 GuestRebecca 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---Timestamps0:00 - Preview & Intro1:48 - Meet Bob London 2:28 - Why "be more strategic" is pressure with no path5:18 - The mindset shift leaders have to make first7:45 - The inverted pyramid and the board question that changes the conversation14:52 - Forget "would you renew?" (ask this instead)20:25 - Why customer-world trigger words work22:18 - The board bullet point question23:00 - How to measure ROI on better conversations27:11 - 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 GuestBob 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---Timestamps0:00 - Preview & Intro1:28 - Meet Andy Mowat (Founder, Whispered)5:28 - How A+ candidates search differently6:52 - Talent partners vs. recruiters and the 340-person Google group10:15 - Career clarity, target lists & the power of loose connections15:20 - Find & connect with the people who have the job you want16:36 - Timing, recency bias, and building real relationships18:50 - Why senior roles are never posted publicly22:44 - Monitoring unposted roles with scrapers and AI23:43 - Why the front door doesn't work25:40 - No more referral fees27:53 - Treat your job search like an outbound sales funnel30:25 - Write thank-you notes31:31 - The CS job market and the coming AI churn wave33:03 - Comp negotiation and why half of all comp numbers are flexible34:45 - 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 GuestAndy 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/