Retention Isn’t Dead. It’s Just Getting Smarter. Brent Krempges, Chief Customer Officer at Gainsight

The Scarcity of Being Human: Catherine Blackmore, Oracle's Group VP of Customer Programs and Employee Success on CS in the Age of Agents

Catherine Blackmore [https://www.linkedin.com/in/catherineblackmore/] has spent nearly two decades building the programs that wrap around technology, from the early days of customer success in 2007 to her current role as Group VP of Customer Programs and Employee Success at Oracle [https://www.oracle.com/]. In this episode she sits down with Justin to unpack what the discipline got right, what it got wrong, and what survives the shift to AI. Catherine makes the case that the high touch model was right all along. It buys a company time to build its moat. But the obsession with the golden record, bridging every data silo, and the red, yellow, green health score was a costly detour, because customers live in their own tools and every account ends up yellow anyway. From there the conversation turns to the question on everyone's mind. If agents can scale the work, what is left for humans? Catherine's answer is that human connection becomes the scarce, valuable thing, and the next generation of CS leaders will manage teams of agents while doing the relational work no agent can fake. She also reframes customer advocacy as the true end state of customer success, the double funnel where your strongest customers become your most believable salespeople. She closes with the career advice she is giving her son as he enters a reshaped workforce. Adaptability beats raw talent, the sum of your experiences equals your existence, and you should always watch the game within the game. What we get into: The high touch model and defending the moat Why the golden record and the red, yellow, green health score never delivered Human connection as the new scarcity model The CSM of the future leading a team of agents Customer advocacy and the double funnel Outcomes over seats and consumption Career advice for the next generation entering an AI-shaped workforce Guest: Catherine Blackmore, Group Vice President of Customer Programs and Employee Success, Oracle

Your Next Role Won't Be Posted, It'll Be Whispered — Andy Mowat

Andy Mowat [https://www.linkedin.com/in/amowat/] has run RevOps at four unicorns, and between every role he's gone out and built something new. His latest is Whispered [https://www.whispered.com/], an AI platform that helps top GTM execs build their careers through shared insights, warm introductions, and access to the roles that never get posted. In this episode, Andy and Justin get into why the entire GTM tech stack is heading for a two-year rebuild, what the move to a data-warehouse-first model means for RevOps teams, and why smaller companies are suddenly more nimble than the enterprise. Andy shares hard-won lessons from scaling Culture Amp, including the speed-to-lead system he built around time-critical leads and the market-maturity question he buried in the win-loss forms. They also dig into whether the fractional exec wave is real, why thoughtful gifting and distinctive events still beat automated outbound, and what it actually feels like to run a proactive job search at the VP level for the first time. A candid conversation between two friends about category strategy, positioning, and building a career in go-to-market when the ground keeps shifting. Buzzsprout Chapter Markers 00:00 — Intro: how Justin and Andy met around Culture Amp  01:40 — Andy's background: RevOps at four unicorns, and why he keeps building  03:30 — Founders as a hiring profile, and the trap of "ambiguous roles"  05:30 — Rebuilding the GTM tech stack: data warehouse first, the semantic layer, and two years of turmoil  07:00 — The give-to-get ratio and why AI-era outbound still comes down to better emails  08:30 — Strategic gifting, distinctive events, and the Wisconsin business school cold open  11:00 — Podcasts as relationship engines, not just content  11:30 — Inside Culture Amp: 180 events a year and the speed-to-lead system  13:00 — The multi-prospect demo experiment, and the market-maturity question that predicts a category's breakout 14:45 — The fractional exec wave: real shift or euphemism for "between jobs" 16:15 — Why early-stage marketing needs people to "grok what you do" before top of funnel  18:00 — What's next for Whispered: the network, the community, and the roles that get whispered

You Can't Read the Label from Inside the Bottle

Justin sits down with Nils Vinje [https://www.linkedin.com/in/nilsvinje/], business growth guide and longtime customer success leader, to talk about the single biggest thing holding most growing companies back: everything still depends on the CEO. Nils spent the early part of his career on the leading edge of the customer success movement — convincing his first employer to ditch the "account manager" title back in 2011 — and has since coached hundreds of CS and CX leaders through the challenge of making their function legible to the rest of the organization. These days he works with CEOs and their leadership teams using the Pinnacle system, a five-principle framework built around people, purpose, playbooks, performance, and profit. In this conversation, Nils and Justin get into what running a CX org teaches you about leadership that no other function can, how to read the label from outside the bottle, and why the hardest decisions in any company are usually the ones everyone already knows need to be made. He also shares what he'd ask anyone standing at a crossroads in their career — and why the answer has nothing to do with money. Chapters [00:00] Intro and What Nils Does Now  [01:42] What Leading a CX Org Teaches You About Leadership  [03:30] The Single Biggest Challenge Every CS Leader Faces  [05:01] Who Nils Works With and When to Bring in Outside Help  [07:08] The Pinnacle System — Five Principles for a Well-Oiled Machine  [09:38] Delivering Hard Truths with Grace  [11:00] The People Problem Most CEOs Won't Solve  [13:08] Why Being Inside the Bottle Kills Objectivity  [14:29] The First Question Nils Asks Anyone at a Career Crossroads  [16:25] What's Next for Nils and the Growth Bottleneck Blueprint  [18:34] Never Stop Adding Value

From Cisco to IBM: How Professional Services Became the Most Important Role in Enterprise Tech w/ Sanjay Pal, WW VP of Software Professional Services at IBM

Justin [https://www.linkedin.com/in/justinlvandehey/] sits down with Sanjay Pal [https://www.linkedin.com/in/sanjaypal12/], Worldwide VP of Professional Services at IBM, to explore what it really takes to lead services at global scale and why the role is more strategically important now than ever before. Sanjay draws on his journey from Cisco to Accenture to IBM to break down what has fundamentally changed about services delivery in the AI era, and what has stayed the same. He shares how IBM thinks about standardizing delivery across 16 global markets without sacrificing client experience, why the forward-deployed engineer model is gaining momentum, and how professional services leaders need to evolve from deployment executors into trusted business advisors. He also shares a personal story about his father, who wrote 52 books with pen, paper, and a stack of research clippings, and what that means for what's possible now. Chapters [00:00] Intro and Sanjay's Path to IBM [02:33] What's Changed in Services, and What Hasn't [05:00] How AI Amplifies Delivery Without Replacing Judgment [08:01] Standardization vs. Customization at Global Scale [10:38] The Evolving Role of the Services Leader [12:44] Forward-Deployed Engineers and Leading with Services [15:02] Breaking Down Silos Across Pre-Sales, Implementation, and Post-Sales [16:05] What's Top of Mind Heading into 2026

From 265 Million Users to Enterprise Gold Standard: How Canva Scales GTM Without Losing Its Soul

Justin sits down with Jessica Chiew [https://www.linkedin.com/in/jessicachiew/], Global Head of GTM Strategy and Operations at Canva [https://www.canva.com/], to unpack what it really takes to evolve from a beloved PLG product into a full-fledged enterprise sales machine without breaking what made it great. Jessica shares how Canva navigates the complexity of multiple handoffs across a PLG-to-SLG journey, why time to value is everyone's job (not just CS), and how she's thinking about marrying product usage data, CRM structure, and conversational intelligence into something actually actionable.  Plus, both Justin and Jessica geek out on the AI and vibe coding moment we're all living through and why it changes everything for revenue teams. Chapters [00:00] Intro & Jessica's Path to Canva Justin welcomes Jessica and she traces her journey from Melbourne to San Francisco, through Asana, and into Canva's B2B buildout. [02:57] Who Owns Onboarding and Time to Value? Jessica breaks down Canva's take on ownership across PLG and enterprise motions — and why success in the first hundred days is a team sport, not a CS problem. [05:57] Moving Upmarket: What Changes (and What Doesn't) From solo users with credit cards to C-suite transformations with change management — how Canva's onboarding approach shifts dramatically as deal size grows. [09:40] Using PLG Signals in an Enterprise World The Asana flashback: how rich end-user data and human relationship context can finally live in the same place, and what that unlocks for enterprise sellers. [11:47] The Tech Stack Behind the Motion CRM alone isn't enough. Jessica walks through how Canva combines structured CRM data, product usage signals, and a full conversational intelligence database to build a real picture of account health. [14:00] AI, Agents, and the Vibe Coding Moment Justin shares his own revelation using AI agents for GTM workflows, and Jessica drops that she recently vibe coded a weekly forecast interface. Neither of them is going back. [16:21] What's Ahead for Canva GTM in 2026 Canva Create in LA, platform updates Jessica can't fully share yet, and the team's focus on becoming the gold standard for enterprise go-to-market.