The Dual Life of a CTO and CISO: Balancing Risk, Speed, and Innovation with Ben Wilcox

This week we sit down with Ben Wilcox, a tech leader who straddles two high-stakes worlds as both Chief Technology Officer and Chief Information Security Officer at ProArch. Ben shares how a teenage interest in “link lists” and web hosting turned into a 25-year career at the intersection of innovation and cybersecurity. We talk about what it really means to balance the drive to move fast with the need to stay secure, and whether those two priorities can truly coexist under one roof.

From high-profile AI prompt injection attacks targeting Microsoft Copilot to the growing sophistication of indirect exploits that manipulate corporate systems through AI agents, Ben breaks down what’s happening behind the headlines and how companies can protect themselves. He also opens up about his passion for car racing, a world that mirrors his approach to tech: fast, calculated, and always built with safety in mind. Ben then closes with some simple advice: say yes to new things, whether it’s tackling the next wave of AI risks or trying something unexpected outside of work, curiosity and courage are what keep you ahead of the curve. 

Ben Wilcox is the Chief Technology Officer and Chief Information Security Officer at ProArch, a global IT consulting firm helping enterprises secure their data and accelerate digital transformation through strategic Microsoft partnerships. With more than 25 years of experience in technology leadership, Ben brings a rare dual perspective—driving innovation while protecting the business from ever-evolving cyber threats. Known for making complex topics approachable, he’s passionate about helping organizations move fast without breaking things, preparing their infrastructure for AI, and building security into the foundation of innovation. When he’s not guiding enterprises through digital change, you might find him on a racetrack, channeling the same balance of speed and precision that defines his work in tech.