EP005: Building Predictive Customer Success with AI w/ Justin Chappell

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