In this high-speed episode of Life of a CISO, Dr. Eric Cole welcomes Ben Wilcox, a rare dual-role executive serving as both CISO and CTO at ProArch — and a race car driver to boot. Ben shares his 30-year journey from building websites in the early internet days to leading enterprise security and technology strategy today.
Dr. Cole and Ben dive into the challenges and opportunities of balancing technical innovation with cybersecurity, how to win executive support for security investments, and how to leverage AI for productivity. Ben also drops valuable advice for aspiring CISOs, emphasizing the power of saying “yes” to new challenges, building business-aligned security strategies, and continuously learning.
This episode is packed with practical insights on executive communication, risk quantification, AI in cybersecurity, and even how lessons from the racetrack apply to the boardroom.
In this episode:
- 01:10 – Ben Wilcox’s career journey: From teenage web entrepreneur to dual-role CISO & CTO
- 05:46 – Why saying “yes” to uncomfortable opportunities accelerated Ben’s career
- 07:32 – How to shift from firefighting to strategic security leadership
- 10:06 – Speaking the CFO’s language: Turning security into business value
- 12:11 – Quantifying risk: How to tie technical threats to real financial impact
- 18:30 – What Ben looks for in mentees and how to attract executive mentorship
- 20:04 – AI in action: How to build internal AI agents that actually save time
- 26:53 – Quantum threats: Should CISOs worry now or wait?
- 29:05 – Ben’s leadership philosophy and favorite quote
- 30:36 – The biggest lesson from race car driving applied to cybersecurity leadership
