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-On or You Won't Get It: If you're in a leadership role and not personally using AI tools like Claude Code or Cursor, you're not fully grasping what's happening right now. Pay the $150 for a month. Just do it.
• Enabling Your Team Is a Different Problem: Discovering an AI tool, getting excited about it, then "schlepping it over the fence" to your team isn't enabling them — it's abdicating. Change management still applies. Help them get on the curve.
• Established SaaS Companies Aren't Dead: Brand trust, enterprise security certifications, and multi-year contracts with durable cash flow give companies like Salesforce and Workday real staying power. The question is whether they'll actually act on it.
• Point Solutions Are Most at Risk: CFOs will start asking whether they need a $40K screen recording tool when it can be vibe-coded in an afternoon. Systems of record with billing, forecasting, and compliance dependencies are much harder to rip out.
• The Juice Is Now Worth the Squeeze: AI lets teams do things they always wanted to do but couldn't justify. Jay built an interactive RACI builder and a conversational applicant tracking system — on a weekend, without writing a line of code.
• It's a Context Problem: The real moat isn't the AI model — it's who can pull together all the Slack threads, call transcripts, emails, and product usage data into one accessible place. That's where the advantage lives.
• Skills Democratize Expertise Across the Team: When any CSM can run the product marketing skill and generate a feature guide on their own, you've removed a bottleneck — not a person. Speed compounds when the whole team can move.
• Token Costs Need a Line Item in Your Budget: Some engineering teams are already capping AI spend at $100K per engineer per year.

CHAPTERS

• 00:00 - Intro and technical issues
• 00:09 - Getting hands-on with AI: why leadership can't just delegate it
• 02:48 - The SaaS market landscape: Jason Lemkin's take
• 08:36 - Why established SaaS companies still have real advantages
• 12:09 - Point solutions at risk; systems of record are defensible
• 16:17 - Jeff's product marketing skill in Claude Cowork
• 20:29 - Democratizing documentation: any CSM can now create the guide
• 22:48 - Feeding source code as context; building a chatbot on your own codebase
• 25:28 - QPR, playbook, and onboarding skill ideas
• 27:19 - Managing token costs and what it means for team budgets
• 28:38 - Jay's interactive RACI builder built with Claude Code
• 34:20 - Balboa GPT: client-contextual AI with shared conversation history

About the Show: Chief Customer Officer Podcast is a show about real strategies for customer-led growth in the AI era—from leaders actually executing, not just talking about it.

Your Hosts:

• Jay Nathan – CEO of Balboa Solutions and Co-Founder of ChiefCustomerOfficer.io
• Jeff Breunsbach – Head of Customer Success at Junction and Co-Founder of ChiefCustomerOfficer.io

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 actionable insights.

KEY TAKEAWAYS

• The CS Evolution Framework: Why moving from reactive → proactive → predictive requires fundamentally different thinking (and why proactive is closer to reactive than you might think)
• The 3 Pillars of World-Class Digital CX: Personalized, Predictive, and Digital-First—and how to operationalize each
• Dirty Data Isn't a Blocker: How predictive models can actually help you identify which data matters while learning from what's usable
• The Power of Simply Asking: Why the best renewal signal is giving customers three options—Yes, No, or Undecided—and how to act on each
• Onboarding That Works: The pilot process that cut first-time-to-value from 44 days to 8 days (and the customer feedback that made it possible)
• The Future CS Team Structure: New roles like AI Architect, Knowledge & AI Readiness Specialist, and Business Value Architect
• Monetizing Customer Success: How success packages create recurring revenue while delivering differentiated experiences

ABOUT OUR GUEST

Justin Chappell is the Head of Digital Strategy at OneTrust, where he oversees digital customer experience for 93% of the company's customer base. He's known for keeping things simple and saying what others are thinking.

Connect with Justin on LinkedIn

CHAPTERS

• 01:17 - The Evolution of Customer Success: Reactive to Proactive to Predictive
• 04:11 - What "Predictive" Really Means (And Why It's Different from Proactive)
• 08:44 - Dirty Data Isn't a Blocker: How Predictive Models Actually Work
• 12:09 - The Truth About NPS Response Rates and Vanity Metrics
• 20:49 - Starting from Zero: Implementing AI at OneTrust
• 23:30 - The 3 Pillars of World-Class Digital Customer Experience
• 31:10 - Lessons Learned: Roles, Timing, and Relevance
• 35:39 - Building the Digital Tech Stack: CRM, CSP, and Community
• 42:15 - Customer-Facing AI Agents: The Agentic CSM
• 46:10 - The Future CS Team: AI Architect, BVA & New Roles
• 53:38 - Managing AI Agents Like You'd Manage Your Best CSM
• 59:24 - How AI Changes the CSM Role (Hint: They Can Handle More)

About the Show:

Chief Customer Officer Podcast is a show about real strategies for customer-led growth in the AI era—from leaders actually executing, not just talking about it.

Your Hosts:

• Jay Nathan – CEO of Balboa Solutions and Co-Founder of ChiefCustomerOfficer.io
• Jeff Breunsbach – Head of Customer Success at Junction and Co-Founder of ChiefCustomerOfficer.io

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 effectiveness of AI agents hinges on their understanding of user preferences and business nuances.

The conversation transitions into a broader discussion about the future of enterprise software, highlighting the need for reliable systems that can integrate AI capabilities while maintaining deterministic workflows.

The hosts also explore the implications of AI on job security and enterprise software, countering the prevailing narrative of doom and gloom. They argue that rather than replacing jobs, AI can enhance productivity by automating mundane tasks, allowing teams to focus on customer interactions. The episode wraps up with recommendations for AI-related resources and discussions on the potential for AI to personalize customer experiences, ultimately leading to more tailored and effective service delivery.

Chapters

00:00 Introduction and Weekend AI Experiments

02:37 The Importance of Context in AI

04:51 AI's Impact on Enterprise Software

08:57 Balancing Deterministic Workflows with AI

11:15 Personalization and Customer Experience

16:38 AI in Developer Tools and Integration

21:32 Recommended Resources and Closing Thoughts

About the Show:

Chief Customer Officer Podcast is a show about real strategies for customer-led growth in the AI era—from leaders actually executing, not just talking about it.

Your Hosts:

• Jay Nathan – CEO of Balboa Solutions and Co-Founder of ChiefCustomerOfficer.io
• Jeff Breunsbach – Head of Customer Success at Junction and Co-Founder of ChiefCustomerOfficer.io