What It Really Takes to Succeed as a CISO | Guest: Matthew Webster

from Life of a CISO with Dr. Eric Cole · host Dr. Eric Cole

In this episode of Life of a CISO, Dr. Eric Cole sits down with cybersecurity leader Matthew Webster to explore what it really takes to succeed in the modern CISO role. Matthew shares his journey from IT into federal and commercial cybersecurity, the lessons that shaped his leadership approach, and why technical skills alone aren't enough at the executive level. Together, they discuss the importance of communication, influence, and business alignment, how CISOs can navigate compliance and legal challenges, and why building strong relationships with executives and legal teams is critical. This conversation offers practical insights for current and aspiring CISOs on translating cyber risk into business value, earning a seat at the table, and leading with clarity in an increasingly complex security landscape.

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This episode is 33 minutes long.

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This episode was published on January 15, 2026.

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