The Chief Customer Officer Podcast

Jay and Jeff go deep on what's actually blocking enterprise AI adoption—and it's not the technology. They cover building a shared organizational brain from call transcripts, why Zapier banned Slack DMs, the $7.5B bet on forward-deployed engineers, and personal AI coaches that are already changing daily habits. KEY TAKEAWAYS Enterprise AI Blockers Are Legal and Cost, Not Tech : The technology is fa...

Jeff and Jay get into the gap between vibe coding your own AI tools and building something your whole team can rely on. From PRD skills to master customer data files to ClickUp's "foundry" model — this episode is about what it actually takes to move from single-player AI to enterprise AI, and why slowing down now might be the fastest path forward. KEY TAKEAWAYS PRDs as AI bumpers : A PRD skill for...

Jay and Jeff are back with a live build episode — two operators comparing notes on what's actually working with AI. From Jay's Agent Command Center at Balboa to Jeff's Linear task ingestion system and a viral VS Code ad hack, this one's packed with real examples. Plus: why the moat in AI is attention, not technology. KEY TAKEAWAYS AI slop is a real leadership problem : Unedited Claude output is hi...

Jay and Jeff kick off the show by getting into the real stuff: managing agent sprawl, why most teams aren't ready for multiplayer AI, and whether tech layoffs actually have anything to do with AI efficiency. Unfiltered and practical. KEY TAKEAWAYS Agent Sprawl Is Everyone's Problem : Agents are spinning up in every tool—Planhat, HubSpot, Gainsight, Claude. Without a team-level agent command center...

Jay and Jeff are joined by Jack Nathan — our "engineering manager" for Uncommon — to share what they've actually shipped in 48 hours using Claude Code. Plus: Gainsight's retention-as-a-service bet, N8N automations surfacing customer quotes in Slack, and why the player-coach is back. KEY TAKEAWAYS Non-engineers can ship now : Jeff (not a developer) built and deployed Uncommon features using Claude...

Jay Nathan flies solo to break down Emergence Capital's AI Native Services Playbook — what it gets right, where it falls short, and what it completely misses. Using a recruiting firm as an end-to-end example, Jay walks through the shift from selling software to delivering outcomes, and why the founders who win in this space won't come from SaaS — they'll come from services. KEY TAKEAWAYS AI Native...

Neil Erickson, Founder and CEO of Owner Enable and former SVP, Global Platforms at Equifax, joins Jay and Jeff to unpack why so many CS and small business leaders feel stuck with AI. The conversation moves from Jeff's live renewal-automation build to context engineering, token economics, and why fundamentals beat shiny objects. KEY TAKEAWAYS Most teams are less mature than they think: Jay's read o...

Jay and Jeff get into the weeds on two of the biggest questions in CS right now: how to build a community that doesn't devolve into spam and consultant pitches, and how the Forward Deployed Engineer role is reshaping who actually sits in front of customers. Plus what Junction is learning about building a product for agents, not just humans. KEY TAKEAWAYS Charge for the community. Paying members se...

Jay and Jeff debrief last week's AI Show & Tell — 150 customer leaders watching four real builds in production. A custom CS platform in Claude Code. A sales reference agent. Renewal workflows that adapt to customer health. Plus the launch of Uncommon, a new community for AI-forward customer leaders: https://www.chiefcustomerofficer.io/uncommon Join us live for AI Demo Day on May 27 at 2pm ET:...

Jay and Jeff swap real examples of building custom AI tools instead of buying software — a $1K brand video that beat $750K agency quotes, a content planner built in 35 minutes, and a renewal digest that surfaces customer context weekly with zero manual effort. Plus: why the CS platform category is stalling, and the difference between a service blueprint and a customer journey. KEY TAKEAWAYS AI col...

Is the CSM role actually dead? Jay and Jeff unpack Chad Hornfeld's viral Avoca post on replacing CSMs with Technical Account Managers and forward-deployed engineers — and what it means for how Jeff is hiring at Junction right now. Plus: Jay's weekend-built HubSpot dashboard, why Claude is winning B2B, and rebuilding onboarding around the patient journey. KEY TAKEAWAYS The CSM role is splitting in...

Jay Nathan goes solo to share what his team at Balboa is actually building—a call intelligence system, Claude-powered skills, and a company operating system called Balboa OS. He also shares the top themes from 90 days of SaaS conversations: broken CSM ratios, the AI sidekick-to-agent gap, messy data, and why onboarding is still the highest-leverage retention moment. KEY TAKEAWAYS - Call Intelligen...

Aurelia Pollet, VP of Customer Experience at CarParts.com , led a small team that built a fully custom AI chatbot and ticketing system from scratch in three months. She shares how they did it, what went wrong when their AI agent Harper made promises it couldn't keep, and why the real value of AI isn't cost-cutting — it's creativity that was never possible before. KEY TAKEAWAYS Build vs. buy is a r...

Jay Nathan and Jeff Breunsbach break down what 50+ CS leaders are actually doing with AI — and what most teams are still getting wrong. Jeff shares fresh takeaways from a Planhat-organized event in Boston, and Jay goes deep on the Claude skills his team has built to scale coaching, standardize deliverables, and rethink how prep calls even work. No hype, just real strategies in the field. KEY TAKEA...

Jay Nathan and Jeff Breunsbach get into the foundational data problem most SaaS teams are ignoring — and why it's about to become a crisis. If your data is siloed, your AI agents will be siloed too. Plus: Jay introduces "Company as Code," a markdown-in-GitHub system for building personalized outreach and landing pages at scale — and why the same playbook applies directly to customer success. KEY T...

Jay and Jeff are back with another hosts-only episode — and Jay builds an AI vulnerability matrix live on the call. They cover how to stand out as an AI-first job candidate, the three biggest AI go-to-market mistakes leaders are making right now, and the heated debate over whether the CSM role is really being replaced or just transformed. KEY TAKEAWAYS Prove you're AI-first before the interview :...

No guest this week — just Jay and Jeff getting into the weeds on what they're actually building with AI right now. From Block's layoffs (and why AI is mostly "air cover" for over-hiring) to MCPs, deal staging from call transcripts, and creating hundreds of renewal records in a single afternoon — this one is all about practitioners doing the work, not just talking about it. KEY TAKEAWAYS AI layoffs...

Jon Olson , Chief Legal Officer at Blackbaud, joins Jay and Jeff to flip the script on what legal teams are actually for. Jon argues that the law department's job isn't to say no — it's to pave the road so the business can move fast. Then the conversation turns to AI: how Blackbaud built an AI council to accelerate adoption, why law is uniquely suited for disruption by LLMs, and what it looks like...

Jay and Jeff are back — and this week it's just the two of them. No guest, no slides. Just a real conversation about what they've each been building with Claude Code and Claude Cowork over the past few weeks, and what it's revealing about the future of software, teams, and CS. Plus a take on Jason Lemkin's SaaS doom post — and why they're not totally buying the narrative. KEY TAKEAWAYS Get Hands-O...

What does world-class digital customer experience actually look like? In this episode, Justin Chappell, Head of Digital Strategy at OneTrust, breaks down the evolution of customer success from reactive firefighting to predictive, AI-powered engagement. Whether you're building your first digital CS motion or looking to integrate AI agents into your customer journey, this conversation offers actiona...

In this episode, Jeff and Jay discuss the evolving landscape of customer success, the integration of AI tools, and the importance of gross revenue retention. They explore the metrics that define customer success roles, the challenges faced by early-stage companies, and the need for clear compensation structures. The conversation highlights the significance of creating effective customer success pl...

In this episode of The Chief Customer Officer Podcast, Jeff Breunsbach and Jay Nathan delve into the evolving role of AI in branding and customer experience. Jay shares his recent experiences using AI tools like Claude and ChatGPT to refine branding strategies for his companies, Balboa and Greenshoot Innovation. They discuss the importance of context in enterprise AI applications, emphasizing that...

The death of the coverage model... In this episode of the Chief Customer Officer Podcast, Jay Nathan and Jeff Breunsbach peel back the layers on the practical application of AI in Customer Success. They start with a reality check: before you can build sophisticated AI agents, you often have to do the manual "grunt work" first — like physically reviewing contracts to clean up renewal data. The conv...

In this episode of the Chief Customer Officer Podcast, Jay Nathan and Jeff Breunsbach discuss the evolving landscape of customer success, particularly focusing on the impact of AI. They explore the importance of building a robust renewal function, identifying key information for renewals, and the necessity of mapping out processes. The conversation delves into the development of granular AI agents...