Summary

On this episode of Chattinn Cyber, Marc is chattin’ with Ben Wilcox, Chief Technology Officer and Chief Information Security Officer at ProArch. Their chat opens by focusing on high-impact, practical ways organizations can reduce cyber risk. Ben highlights identity as the top priority: his team moved to passkeys to remove passwords and lower the attack surface. He stresses that threat actors increasingly use man-in-the-middle techniques and that AI has accelerated the automation of credential-theft, which makes strengthening identity controls essential.

The chat then moves to AI and data governance. Ben describes rolling out visibility tools to monitor internal AI use — what prompts users run and what data is fed into models — and pairing that with data labeling and classification. He warns organizations to restrict where AI tools are allowed and to implement compensating data controls to prevent accidental or intentional leaks of sensitive information.

Ben cautions that AI and cybersecurity must be adopted in parallel, because AI will reveal existing misconfigurations and permission drift. He gives practical examples (like Copilot showing information a user shouldn’t see because of incorrect permissions) to illustrate how AI surfaces weaknesses in access controls. The takeaway is that AI can be a force-multiplier but also a magnifier of existing security gaps.

On leadership and tradeoffs, Ben explains how combining CTO and CSO responsibilities can be an enabler if balanced correctly. He argues for marrying a product/technology lens with a risk lens, leveraging internal expertise, and making business enablement and security complementary so organizations can move quickly while maintaining the right groundwork.

Finally, Ben addresses translating cyber risk into financial terms for CFOs and boards. He recommends business impact analysis—linking key system outages (e.g., Active Directory) to production downtime costs—to quantify risk and justify security investments. He shares real incident cost ranges (low seven figures to tens of millions in some cases), underscores the role of compensating controls, and concludes with a call to monitor industry trends, assess outage and reputational costs, and prioritize risk reduction.

Key Points

Identity-first approach: move away from passwords (passkeys) and reduce reliance on MFA tokens that can be intercepted or automated by attackers.
AI visibility and data controls: monitor internal AI usage, restrict sites/tools, and enforce labeling/classification to prevent data leakage.
AI exposes existing weaknesses: adopting AI without fixing permission drift and misconfigurations surfaces risks rather than hiding them.
Speed and detection advantage: AI can accelerate detection and response in SOCs—gaining even seconds can materially reduce impact.
Translate risk to business terms: use business impact analysis to quantify downtime costs and build the financial case for security investments and insurance.

Key Quotes

“Last year we took the initiative and we moved to pass keys.”
“AI has sped up that weaponization and being able to turn that around and get those tokens automatically.”
“AI is going to expose the weaknesses that are inherent within your security controls that you already have in place.”
“If we can get even 5 seconds faster or 10 seconds faster or 20 seconds faster, sometimes that makes a difference.”
“And that’s why they should have bought cyber insurance.”

About Our Guest

Ben Wilcox is a seasoned technology leader with over 25 years of experience driving innovation and solving complex business challenges. Serving as both Chief Technology Officer and Chief Information Security Officer at ProArch, Ben combines a forward-looking vision with a hands-on approach to cybersecurity. He is passionate about leveraging technology to accelerate business outcomes while embedding security best practices into organizational culture and operations. Ben’s strategic mindset and dedication to excellence have strengthened ProArch’s resilience and helped protect clients’ data and systems. Outside of work, Ben channels his relentless drive into racing as an instructor and competitor with the Northeast Audi Club, and enjoys gardening, cooking, and spending quality time with his family. As he puts it, “Security isn’t just about defending against threats—it’s about enabling trust, protecting growth, and ensuring every decision we make strengthens the foundation of the business.”

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About Our Host

National co-chair of the Cyber Center for Excellence, Marc Schein, CIC,CLCS is also a Risk Management Consultant at Marsh McLennan Agency. He assists clients by customizing comprehensive commercial insurance programs that minimize the burden of financial loss through cost effective transfer of risk. By conducting a Total Cost of Risk (TCoR) assessment, he can determine any gaps in coverage. As part of an effective risk management insurance team, Marc collaborates with senior risk consultants, certified insurance counselors, and expert underwriters to examine the adequacy of existing client programs and develop customized solutions to transfer risk, improve coverage and minimize premiums.

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Beyond Passwords: Passkeys, AI & Identity with Ben Wilcox