The Chief Customer Officer Playbook for the AI Era
A clear, practical path to lead the AI transition, prove results, and future-proof your career.
If you were designing how your organization creates and delivers customer value today, knowing what AI makes possible, what would you build?
Most post-sale organizations are already using AI. They have launched pilots, tested tools, and found early wins. Yet when the conversation turns to what actually changed in retention, expansion, or cost-to-serve, the answer is often unclear. The problem is not the technology. It is the leadership model for applying it.
The Chief Customer Officer Playbook for the AI Era gives customer and post-sale leaders nine practical strategies for moving from scattered experimentation to measurable results. It shows you how to define the right AI agenda, redesign work and customer experiences, build an operating model, lead your team through change, and measure impact on the business metrics your executive team already tracks.
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This Is Not Another AI Book
You do not need another book explaining what AI is.
You do not need another list of tools, prompts, or productivity hacks.
You need a leadership playbook for answering the questions post-sale leaders are facing now:
- Where should AI matter most in our organization?
- How do we connect AI initiatives to business outcomes?
- How do we redesign workflows instead of layering new tools onto old processes?
- How do we move from scattered pilots to a coherent strategy?
- How do we measure impact and prove ROI?
- How do we improve customer outcomes without sacrificing trust and relationships?
The Chief Customer Officer Playbook for the AI Era helps you answer those questions and move from insight to action to results.
What You Will Learn
The book is organized around nine practical strategies, taking you from defining your AI agenda all the way to owning the customer experience your organization delivers.
Define Your AI Agenda
Develop AI Fluency
Build the practical AI knowledge and leadership confidence required to make better decisions, guide your team, and challenge assumptions.
Pilot with Purpose and Scale Fast
Build Your AI Operating Model
Redesign The Work, Not the Tools
Make Using AI the New Standard
Lead Your AI-Enabled Team
Measure AI Impact, Not AI Activity
Own the Customer Experience
Early Praise for
The Chief Customer Officer Playbook for the AI Era
“A must-read for every CCO and post-sale leader navigating this AI transformation. Rod lays out exactly what it takes to move from AI experimentation to results.”
“There’s no shortage of AI hype, but precious little guidance on what to actually do about it as a post-sale leader. This book fills that gap brilliantly.”
From AI Adoption to Redesign
The nine strategies get your team using AI well. The harder question comes next. If you were designing how your organization creates and delivers customer value today, knowing what AI makes possible, what would you build?
Most leadership teams work through that question in three steps.
Start with your AI Strategy on a Page.
Most leaders are working on too many things at once. This gets your AI agenda down to one page: the outcome you own, what is blocking it, and where AI actually helps. The book shows you how to create it or Rod can work with your team to define it.
Then build your Redesign Blueprint.
Then make it real.
What Becomes Possible When You Redesign the Work?
Imagine an onboarding experience that adapts to each customer’s goals, risks, level of expertise, and progress.
Imagine a renewal process that identifies risk, assembles the business case, and prepares the account team before the customer raises a concern.
Imagine Customer Success Managers entering every meeting with a complete view of the customer’s priorities, product usage, commitments, risks, and next-best actions.
This is what redesigning customer value looks like in practice. This book shows you how to get there.
Who The Chief Customer Officer Playbook for the AI Era Is For
This book is written for Chief Customer Officers and the leaders responsible for what happens after the sale, including:
- Customer Success and Account Management leaders
- Professional Services and Implementation leaders
- Customer Support leaders
- Customer Education and Community leaders
- Renewals and expansion leaders
- Customer Experience leaders
- Aspiring post-sale executives
- CEOs, operating partners, and senior executives responsible for customer growth
You do not need to be an AI expert.
You do need to be ready to make decisions, challenge old assumptions, and lead your organization through change.
About the Author
Rod Cherkas has spent his career as a post-sale executive and trusted advisor to CEOs, CCOs, and their customer-facing teams. He worked at several of the world’s most customer-centric companies, including Intuit, RingCentral, Marketo, and Gainsight. He is currently the Founder and CEO of HelloCCO, a strategy consulting firm that partners with innovative companies across diverse industries to develop, execute, and scale strategies for their customer-facing functions.
His work helps companies improve customer retention, increase profitability, drive expansion revenue, and accelerate AI transformation. He is the author of the bestselling books The Chief Customer Officer Playbook and REACH: A Framework for Driving Revenue Growth from Your Existing Customers. His third book, The Chief Customer Officer Playbook for the AI Era, will be published on September 9, 2026. He is also the Chair of the AI in Post-Sale Council.