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

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

Summary

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 plans and the necessity of aligning customer success efforts with overall business goals.

Takeaways

AI tools are transforming how we approach customer success. Customer success metrics are often poorly defined across organizations. Gross revenue retention is becoming a critical focus for investors. The structure of customer success teams can impact their effectiveness. Compensation for customer success roles needs to reflect their contributions to revenue. Early-stage companies must prioritize customer success to drive growth. Separation of roles within customer success can lead to better outcomes. Customer success should be a company-wide initiative, not just a team effort. Creating autonomy for customer success teams can enhance performance. Defining clear success plans is essential for customer retention.

Chapters

00:00 Website Redesign and AI Integration

02:50 The Evolution of AI Tools

05:28 Customer Success Metrics and Reporting

08:18 The Role of Customer Success in Revenue Generation

11:09 Compensation Structures in Customer Success

14:06 Strategic Decisions in Customer Success

16:51 Navigating Growth in Early-Stage Companies

26:40 Sales Strategy and Market Share Growth

28:21 Customer Success and Implementation Challenges

30:06 Specialization in Customer Success Roles

32:14 Creating Autonomy and Predictability in Sales

34:51 Understanding Private Equity and Its Impact

37:37 The Importance of Gross Revenue Retention

40:16 The Role of Customer Success in Retention

43:07 Innovative Approaches to Customer Success Plans

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 conversation shifts to a critical debate on organizational structure, specifically the move away from the traditional "Coverage Model" (assigning accounts based on ARR) toward a "Predictive Model" that relies on real-time data signals rather than arbitrary check-ins. Finally, Jay and Jeff geek out on the concept of "Vibe Coding" — using AI to build internal tools and websites without writing a line of code — and discuss why leaders need to get their hands dirty with these tools to truly understand them.

Chapters

00:00 Introduction & Dropping the ".io" 01:07 The Reality of Renewals: Manual Work Before AI 04:49 Why You Should Hire Ops Before Your Next CSM 09:49 The Death of the Coverage Model 13:49 Erroneous Signals vs. Predictive Data 17:44 The Evangelism Role & Fixing QBRs 25:36 The "Stay Conversation": 3 Questions to Retain Your Team 27:42 "Vibe Coding" & Building Software with AI 33:25 How Jeff Built the New Website (Without Code) 42:34 Preview: Sierra AI & Next Week

And we're back...

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 to enhance customer interactions and the balance between workflow and AI capabilities. They also emphasize the significance of understanding customer business contexts and choosing the right tools for effective AI implementation. The episode concludes with thoughts on standardizing AI use across teams and the future directions of AI in customer success.

Chapters

00:00 Introduction to the Chief Customer Officer Podcast 02:58 The Role of AI in Customer Success 05:58 Building a Renewal Function with AI 08:49 Identifying Key Information for Renewals 12:08 Mapping Out the Renewal Process 15:09 Creating Operational Agents for Efficiency 18:10 The Future of AI in Customer Engagement 22:09 Optimizing Workflow with AI Agents 24:18 Personalization in Customer Interactions 26:11 The Importance of Real-Time Data 28:00 Exploring Tools for AI Integration 30:04 Categories of Agentic Tools 35:50 Empowering Business Users with Agent Development 39:04 Real-World Applications of AI in Business

Keywords: renewals, customer success, AI, SaaS, customer experience, chief customer officer, renewal process, agentic tools, customer engagement, technology in business, customer retention