The CEO’s AI Dilemma

An Authentic Growth® Webinar Event

About This Webinar

If you’re a CEO right now, you’re probably holding two things at once: genuine excitement about what AI could do for your business, and the weight of knowing you’re supposed to be the one leading the charge. You’re not alone.

Every CEO we know is navigating some version of the same tension. The pressure to adopt AI is real — but so is the confusion about where to start. Should you invest in enterprise AI licenses? Wait for your existing platforms to catch up? Build something custom? And when exactly are you supposed to figure all this out on top of the job you already have?

This isn’t a webinar with tidy answers. It’s a peer-to-peer conversation between four CEOs — leading very different businesses — who are all in the middle of it right now. They’ll share what’s keeping them up at night, where they’re placing our bets, what they’ve learned so far, and what they’re still figuring out.

The first installment of this series was about how experienced marketing leaders are guiding AI innovation on the ground. This one is about the view from the CEO’s chair — where the excitement is real, the stakes are high, and the to-do list never stops growing.

What We’ll Discuss

  • The emotional reality of leading through AI — the excitement, the overwhelm, the fear of falling behind, and how CEOs are managing all of it at once.
  • The “where do I even start?” question — how each CEO approached (or is approaching) the first real AI decisions in their business.
  • Buy, build, or wait? — the technology investment dilemma: enterprise AI licenses, platform-native AI, custom solutions, or some combination — and how these CEOs are thinking through the trade-offs.
  • Leading the change when you’re still learning yourself — how to bring your leadership team along on the AI journey when you don’t have all the answers yet.
  • What’s on the roadmap — where each CEO is placing their bets for the next 12 months and what experiments are underway.
  • Finding the time — the honest conversation about how CEOs who already work 60-hour weeks are carving out space to learn, think, and lead through AI on top of everything else.

This webinar is for CEOs, founders, and senior leaders who are in the thick of it — running a growing business while trying to figure out what AI means for their company, their team, and their own role as a leader. If you’ve felt the pull between wanting to move fast and not knowing which direction to move, you’ll find yourself in this conversation.

Webinar Details

May 6, 2026
12:00 – 1:00 PM CST

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