Truth, Not Hype:
How CIOs Can Survive AI Vendors

Enterprise AI vendors and salespeople promise easy implementations and amazingly useful features, yet many buyers never reach that enterprise technology promised land. Instead, high costs, vendor lock-in, and confusion often reign.

We explore solutions to these problems and more, with Kyler Cheatham, co-founder and Chief Performance Officer of The Confluencial, where she advises CIOs and CFOs on enterprise SaaS software purchases.

Key points:

• Plug-and-play AI still needs permissions, integration, clean data, approval rules, security testing, and a process owner before it works.
• Under usage-based pricing, an AI product costs more the more it is used, and buyers are left to define its value themselves.
• Dependence on a vendor is a form of technical debt, Cheatham argues, and few companies account for it that way.
• After a failed go-live, buyers often face change orders and new licenses for the functionality they thought they had already bought.
• Cheatham says due diligence is the buyer’s job alone, and she traces failed technology projects to the leaders who ran them.

Join this interactive session with Kyler Cheatham live on Friday, October 30, 2026, at 1:00 PM ET on CXOTalk. Subscribe for key takeaways from every episode and advance notice of live shows.

Episode Participants

Kyler Cheatham is Chief Performance Officer at The Confluencial, an enterprise technology advisor firm. She calls herself "public enemy #1 of overpriced SaaS solutions that add no value."

Michael Krigsman is a globally recognized analyst, strategic advisor, and industry commentator known for his deep business transformation, innovation, and AI leadership expertise.