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Interview

The Biggest Marketing Lessons From Season 2 of The CMO Circle

3 minute read
Michelle Hawley avatar
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A look back at Season 2 of The CMO Circle and the biggest lessons CMOs shared about AI, leadership and growth.

The Gist

  • Marketing in the Age of AI. Season two of The CMO Circle revealed that human connection remains marketing’s most valuable differentiator.
  • The Key to AI Success. Multiple guests emphasized that AI success depends on strong foundations, collaboration and intentional leadership — not tools alone.
  • How to Achieve Sustainable Growth. Across budgets, brand sizes and industries, CMOs agreed that real growth comes from doing right by customers and teams.

Season two of The CMO Circle wrapped with a clear throughline: while AI is reshaping marketing at every level, the fundamentals of leadership, trust and collaboration haven’t changed. If anything, they’ve become more important.

Throughout the season, conversations spanned everything from marketing on a shoestring budget to the inner workings of multimillion-dollar customer programs, the evolution of century-old brands and what CMOs should be preparing for next. Despite the range of perspectives, almost all can agree that while technology accelerates strategy, people still define it.

Table of Contents

Human Connection Is Non-Negotiable — Even as AI Scales Marketing

Several guests returned to the same caution: automation and efficiency cannot come at the expense of authentic customer relationships.

One example centered on customer marketing and the risk of mistaking scalability for sustainability. As guest Christine Dart, former Global Head of Marketing at Helpshift, explained, "Sometimes when you have one customer that's really excited to participate with you… it's kind of easy to want to be like, so and so loves doing this. We'll ask them again.” But that approach breaks down quickly. Ask a customer to participate too many times, and they might start to shy away. 

In an era where AI makes it easier to identify, activate and reuse advocates at scale, efficiency can’t replace judgment. Relationships still require restraint, empathy and respect for the human on the other side.

That mindset extends into other areas of AI-driven marketing. As one discussion with Grammarly CMO Lena Waters revealed, “The people who use our product and make the decisions are still human,” and brands must continue to “connect with them and appeal to them on a human level.”

The takeaway: AI should enhance empathy, not replace it. Reagan Attle, CMO at Clio, summed it up: “Our customers need to believe that we care through our actions.”

AI Only Works When the Foundation Is Right

Another major theme of the season was the misconception that AI success starts with tools. Guests consistently pushed back on that idea, emphasizing structure, integration and data readiness.

“If you don't have the right team structure, it doesn't matter if you have all the AI in place,” Paula Mejia, VP of Marketing at Wix, noted. Even with advanced tools, disconnected systems limit value: “If you have all the AI in place, but the different AI tools don't connect to each other… you don't get the most bang for your buck.”

Data quality emerged as another non-negotiable baseline. “The AI only knows what you tell it,” said CMSWire contributor Brian Riback, adding that without foundational data, “you're just driving a three wheel car up the road.”

Collaboration, Not Silos, Builds Enduring Brands

Across conversations about legacy brands, fast-growth companies and AI-first organizations, one constant surfaced: strong brands are built collaboratively. “Great brands don't get built in silos,” Genpact CMO Caitlin Blewett said plainly. 

This sentiment applies not only to internal teams, but also to how brands work with customers, partners and technology. Whether discussing AI adoption or customer engagement, guests stressed that progress requires cross-functional alignment and shared ownership.

Learning Opportunities

The most successful marketing organizations, many agreed, are the ones that treat collaboration as a core operating principle — not a side initiative.

Season 3 Is On the Horizon 

If we learned anything in season two of the CMO Circle, it's that AI may change how marketing gets done, but it doesn't change what great marketing requires. 

Empathy, strong foundations and collaboration all remain the pillars. AI simply raises the stakes.

With season three on the horizon, the conversations are only getting sharper. Check back soon for more insights from marketing leaders navigating what comes next.

About the Author
Michelle Hawley

Michelle Hawley is an experienced journalist who specializes in reporting on the impact of technology on society. As editorial director at Simpler Media Group, she oversees the day-to-day operations of VKTR, covering the world of enterprise AI and managing a network of contributing writers. She's also the host of CMSWire's CMO Circle and co-host of CMSWire's CX Decoded. With an MFA in creative writing and background in both news and marketing, she offers unique insights on the topics of tech disruption, corporate responsibility, changing AI legislation and more. She currently resides in Pennsylvania with her husband and two dogs. Connect with Michelle Hawley:

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