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Why I’m Creating the AI in Post-Sale Council

Why I’m Creating the AI in Post-Sale Council

Over the past year I’ve had dozens of conversations with post-sale leaders about AI from different companies, industries, and levels of maturity. But the questions are remarkably consistent:

  • Who should own AI in post-sale?
  • How do we move from experimentation to measurable outcomes?
  • How do we upskill teams without creating fear or fatigue?
  • What should we be telling our executive teams and boards?
  • How do we make decisions when the technology is evolving faster than our operating models?

What’s become clear is this: AI in post-sale is not a problem leaders should be solving alone.

The Purpose Behind the AI in Post-Sale Council

AI isn’t just introducing new tools into Customer Success and post-sale organizations. It’s forcing decisions about ownership, workflows, governance, talent, measurement, and trust at a pace most leaders have never experienced before.

And while there’s no shortage of AI content, there is a shortage of practical, peer-level guidance specifically for post-sale leaders. That gap is why I’m creating the AI in Post-Sale Council.

The Gap I Keep Seeing in AI Adoption

Most post-sale teams are doing the right thing. They’re experimenting with AI tools, finding productivity gains, and learning what’s possible. But as executive expectations rise, tension is growing:

  • Experimentation is easy to start, hard to operationalize
  • Productivity gains are real, but difficult to translate into retention or expansion outcomes
  • Responsibility for AI is shared, but accountability for results is unclear
  • Leaders are being asked to defend impact before they’ve had the chance to shape direction

This creates a quiet isolation.

Leaders know AI matters and that they need to move forward intentionally. But they’re often making structural decisions in a vacuum, without visibility into how peers are approaching the same challenges.

Why a Council, Not Another Framework or Event

I didn’t want to create another report, conference, or tool-centric community. What’s missing is a peer-led space where post-sale executives can work through hard leadership questions together, not as finished experts, but as practitioners navigating change in real time.

A place to:

  • Compare approaches to AI ownership and governance
  • Share what’s working and what isn’t
  • Talk candidly about workforce impact and change management
  • Develop shared language and emerging best practices
  • Learn without pressure to “have it all figured out”

AI in post-sale is a leadership and operating model challenge, not just a technology one.

What the AI in Post-Sale Council Is Designed to Be

The AI in Post-Sale Council is a peer forum for senior post-sale leaders navigating the long-term structural impact of AI. It is:

  • Focused on operating model evolution
  • Built around real-world implementation
  • Grounded in shared research and practical application

It is not:

  • A vendor showcase
  • A product evaluation group
  • A hype-driven AI community

The goal is simple: help post-sale leaders make better AI decisions with more confidence and less risk.

Why Now?

AI adoption in Customer Success is still early. But expectations are accelerating quickly. The decisions leaders make now about:

  • AI ownership
  • Workflow redesign
  • Measurement alignment
  • Enablement and fluency

…will shape how post-sale organizations operate for the next decade. The profession will move faster and more responsibly if leaders work through this together rather than independently reinventing solutions.

What Happens Next

The AI in Post-Sale Council is launching gradually alongside ongoing benchmark research, webinars, and industry discussions. Early participation is invitation-based and focused on contribution and shared learning, not scale.

If you’re a senior post-sale leader wrestling with AI strategy, operating model design, or maturity progression, I’d encourage you to join the conversation. Learn more about the AI in Post-Sale Council and request information here. 

AI in post-sale is too important, and too complex, to navigate alone. Until that decision is made, teams will continue to make progress that feels real but remains difficult to translate into results that matter.

👉 Curious how AI can amplify your customer success outcomes? Contact me or schedule a strategy session.

Rod Cherkas

Rod Cherkas is a well-respected consultant, advisor, author, and speaker. He has been a post-sale executive at several of the world’s most customer-centric companies including Intuit, RingCentral, Marketo and Gainsight. He is 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 clients rave about their “repeatable results with Rod”.

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