Everyone Else Seems to Have AI Figured Out. Do They? ft. Rod Cherkas (HelloCCO)

If you go by what you see on LinkedIn, it looks like every retention leader is rolling out AI agents and flipping their whole organization on its head overnight. But after speaking with nearly 200 post-sales leaders, Rod Cherkas found a very different reality.

In this episode of [Un]Churned, “215. Your CFO Wants Proof: Is Your AI Paying Off?,” Josh Schachter sits down with Rod, CEO of HelloCCO and author of The Chief Customer Officer Playbook for the AI Era, to separate AI ambition from reality. They dig into what’s holding leaders back, the build-versus-buy debate, how to turn AI investments into measurable results as 2027 approaches, and what the future holds for the CCO and the teams they lead.

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🎯 The [Un]Churned Take: The Clock Is Ticking on Experimental AI Budgets

Remember when getting everyone on your team to use AI felt like a huge deal? You introduced new tools, rallied everyone around them, and maybe even had some good examples to share at your next all-hands. Now, priorities are shifting, and this year’s investments need to prove their value.

In this week’s episode of the [Un]Churned podcast, “215. Your CFO Wants Proof: Is Your AI Paying Off?”, Rod Cherkas, CEO of HelloCCO and author of The Chief Customer Officer Playbook for the AI Era, talks about what he’s learned from talking to almost 200 post-sales leaders about their experiences with AI. As companies look ahead to 2027, he’s seeing expectations start to change.

“I think what CFOs are starting to see is sort of the credit card charges for the Anthropic and OpenAI on their invoices and saying, hey, what are we getting out of that?”

_{Rod Cherkas, CEO of HelloCCO}

In the last few years, companies have spent money on AI tools, training, and pilot programs, often with high but sometimes unclear expectations. Many of these investments have made a real difference. Teams are saving time, automating routine tasks, and discovering new ways to get things done.

But as planning for the next fiscal year begins, expectations are rising. It’s no longer enough to just use AI. Now, companies need to show how these investments are improving the business metrics that matter most.

So You Saved Five Hours. Now What?

Imagine your team brings in an AI assistant that saves each CSM five hours a week. That’s a big productivity boost, especially across the whole company. But how are those five hours actually used?

Are CSMs using that extra time to connect more with customers? Are they spotting churn risks sooner or finding new growth opportunities they might have missed before? Or are they just clearing out their inboxes faster?

Making daily work easier is a win, but saving time doesn’t always create real value. If that extra time doesn’t lead to something important for the business, it’ll get harder to defend the investment.

The same idea applies to adoption. Having 90% of your team using AI might look impressive on a dashboard, but it doesn’t really show if your retention strategy is improving.

“It’s gonna be important for leaders to think about how you drive not just the activity, but initiatives that are changing results in the metrics your company cares about.”

_{Rod Cherkas, CEO of HelloCCO}

Your AI Strategy Is Backwards

Since AI became popular, most people have asked, “How can we use AI?”

Along the way, we’ve made some exciting discoveries, but it’s also encouraged teams to collect use cases like trading cards, experimenting with everything from meeting summaries to automated customer communications without always knowing what success should look like.

Now, as we look toward 2027, it’s time to flip the question. What does your business need to achieve next year? Is it better retention, more growth, or lower costs? Where can AI really help you reach those goals?

“I’m doing work with clients now, as we’re thinking about the 2027 planning process, to think about the four or five most important metrics in your organization. And then how can you align your AI initiatives around one or two of them to actually move the needle.”

^{Rod Cherkas, CEO of HelloCCO}

The most advanced AI project isn’t always the most valuable. Sometimes, simply automating a complicated sales-to-post-sales handoff can improve the customer experience more than a complex tool that no one really uses.

From Experimentation to Expectation

The AI experiments we’ve done so far have set us up for what’s next. We’ve learned what AI can do, how to use it in our operations, and how to test new ideas as they emerge.

But as we look to the future, expectations are growing along with the opportunities. As we plan the next phase of our AI strategies, we need to make sure our investments lead to real results. Not just more productivity, but true impact on the bottom line.

Not every experiment will be a big success, and not every result will show up in your data right away. That’s just part of the process.

Real progress happens when you know your goals and track the impact as you go. Your CFO isn’t looking for another AI assistant demo. They want to see what new opportunities it can create for your business.

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🎧 Listen for These Moments

From rethinking your tech stack to reshaping your team’s roles, retention leaders have some big decisions ahead. Here are a few moments worth tuning in for.

• The unexpected roadblock to AI transformation: Why some of the biggest barriers to AI adoption are coming from leadership, not the front lines, and what executives need to do differently.

• The build-versus-buy reality check: Just because you can build your own AI-powered solution doesn’t mean you should. Rod breaks down the hidden complexities of maintaining homegrown technology.

• The future of the CCO (and the CSM): Will AI shrink retention teams or make their work more valuable? Rod shares his predictions for how roles, responsibilities, and customer relationships will evolve.

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🔎 Where to Find the Speakers

• Rod Cherkas — https://www.linkedin.com/in/rodcherkas/

• Josh Schachter — LinkedIn: https://www.linkedin.com/in/jschachter/

📎 Referenced in This Episode

• The Chief Customer Officer Playbook for the AI Era — Rod Cherkas’s latest book on leading post-sales organizations through AI transformation.

• HelloCCO — Rod’s consulting and advisory business.

• AI Post-Sales Council — The community Rod founded to help post-sales leaders navigate AI adoption and transformation.

• David Karp — Billtrust’s SVP of CS and former [Un]Churned guest (check out his episode here). Referenced for his work automating sales-to-post-sales handoffs with AI.

• Abbas Haider Ali — Atlassian’s CCO and former [Un]Churned guest (check out his episode here). Referenced for his approach to measuring the efficiency and financial impact of AI-powered support.

• Marketo — Discussed as an example of how technology reshaped an entire generation of marketing leaders.

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Wrapping Up

The AI experimentation era gave everyone permission to play, but 2027 is the year someone checks the scoreboard.

See you next week 🧠