Charles Henderson, Coalfire

In this #BlackHatUSA 2025 segment, theCUBE’s Jackie McGuire sits down with Charles Henderson, EVP of Division Hex at Coalfire, to discuss the launch of this newly formed security unit and how it aims to push beyond commodity services to deliver impactful, threat-informed results. Henderson shares his personal journey from early DEF CON days to leading elite offensive and defensive teams, highlighting how curiosity, a strong moral compass and a passion for security drive the Division Hex culture.

The conversation dives deep into the state of enterprise security in the era of AI adoption, including the risks from agentic AI applications, why Coalfire’s AI penetration tests have uncovered critical vulnerabilities 100% of the time and how the low cost and rapid deployment of AI bypass traditional security checkpoints. Henderson explains how Division Hex is tackling these challenges with targeted offensive testing, advanced threat hunting, hardware and AI hacking, and managed services designed for scalability and elite execution.

McGuire and Henderson also explore the strategic need for visibility and trust as AI becomes the new “shadow IT”, the importance of securing innovation without stifling it and why orchestration across security functions is essential for defending against scalable threats. Henderson underscores the urgency for CISOs to proactively test, model threats and assess compromises before the “worst day” hits, ensuring that tools and teams are prepared for rapid, coordinated response.

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