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Scott Smeester

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Founder at CIO Mastermind

Scott Smeester is the founder of CIO Mastermind, which helps CIOs and senior technology leaders with executive alignment, decision-making, and turning technology investment into business value. He started his first technology company in 1995 and has spent the decades since building companies and translating between the executive suite and the IT organization. https://www.ciomastermind.com/

Leadership
Enterprise AI
Security, Governance, & Risk
Orchestration & Agentic AI

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Scott Smeester

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Leadership
September 15, 2026

Your Most Expensive Knowledge Gap Is Not The Board's

Scott Smeester argues the costly AI knowledge gap lives between CEO and CIO, not CEO and board, and briefings won't solve it.

Leadership
August 4, 2026

The Real Cost of Not Canceling Anything

Scott Smeester argues roadmap inflation isn't a prioritization problem. It's a missing decision, and CIOs need a kill list to fix it.

Enterprise AI
July 14, 2026

When The AI Bill Lands On The CFO's Desk, CIOs Need To Be Ready

The AI bill is coming for everyone. CIO Mastermind founder Scott Smeester explains how technology leaders can avoid getting caught flat-footed.

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