AI vendors promise easy implementations and charge more the more their products are used, which leaves buyers with costs they cannot predict and contracts that are hard to leave.
Join me for a live, interactive discussion where buyer’s advocate Kyler Cheatham explains how CIOs and CFOs can test vendor claims before they sign.
Software prices keep rising at renewal: 79% of IT leaders encountered price increases at SaaS renewal in the past 12 months, according to Zylo’s 2026 SaaS Management Index. AI products add a new problem, because their price grows with every use.
In Episode 935, I talk with Kyler Cheatham, co-founder and Chief Performance Officer of The Confluencial, about how buyers can separate AI vendor hype from reality, what belongs in an AI contract, and what leaders must own after they sign.
At The Confluencial, an enterprise technology advisory firm, Cheatham advises CIOs and CFOs on enterprise software purchases. She also makes short videos that act out how enterprise software is sold, and her most-watched videos have passed one million views on TikTok. This is her first CXOTalk appearance.
What Kyler will discuss:
- How enterprise buyers can separate AI vendor hype from reality
- What it takes to make AI work inside a company’s existing systems
- The effect of usage-based pricing on what buyers pay
- What CIOs and CFOs should insist on in an AI contract
- When to stop funding a stalled project and walk away
- Advice for CIOs and CFOs before their next AI contract or renewal
Join this interactive session with Kyler Cheatham live on Friday, October 30, 2026, at 1:00 PM ET on CXOTalk.
The conversation is live, and your questions are part of it. Ask Kyler anything in the LinkedIn Live chat, or on X with the hashtag #cxotalk and @mkrigsman, and I will bring your questions into the discussion.
JOIN LIVE AND PARTICIPATE
Friday, October 30
10am PT / 1pm ET
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EPISODE PARTICIPANTS
Kyler Cheatham is Chief Performance Officer at The Confluencial, an enterprise technology advisory 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 expertise in business transformation, innovation, and AI leadership.
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UPCOMING LIVE SCHEDULE
See www.cxotalk.com for the latest updates to our live programming schedule.
Oct 30: Kyler Cheatham, Chief Performance Officer, The Confluencial
Nov 6: China Widener, Vice Chair, Deloitte
Nov 13: Hari Gopalkrishnan, Chief Technology & Information Officer, Bank of America
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Recent Editions
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- Occidental’s Chief AI Officer: AI at Scale in the Physical World Sep 15, 2026
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