The Real State of Offensive Security: AI, Penetration Testing & The Road Ahead with Andrew Wilson

Tom Eston interviews offensive AI researcher and PhD candidate Andrew Wilson, a former Bishop Fox partner who helped grow the firm from under 20 people to nearly 500, built award-winning AI solutions for SOC modernization, founded Cactus Con, and relocated his family to Guadalajara to open and scale a Bishop Fox office. They discuss Mexico’s growing cybersecurity and AI ecosystem, driven by talent, community events, and government-university partnerships, and how offensive security has shifted from “one-person army” generalists to more specialized roles. Wilson explains his PhD work modeling expert pen testers’ cognitive approaches to shape AI agents, argues AI lowers barriers but requires validation due to hallucinations, and predicts routine, methodology-driven testing will be automated while expert human work persists. He forecasts compliance and audit frameworks will eventually accept more objective, scalable AI-based control validation, reshaping the pen testing market. If you work in cybersecurity, involved in penetration testing and offensive security, or are just trying to figure out what the AI hype actually means for attackers and defenders, this episode is for you! ** Links mentioned on the show ** Follow and connect with Andrew Wilson Find out more about CactusCon! ** Watch this episode on YouTube ** ** Become a Shared Security Supporter ** Get exclusive access to bonus episodes, listen to new episodes before they are released, receive a monthly shout-out on the show, and get a discount code for 15% off merch at the Shared Security store. Become a supporter today by going to our YouTube channel’s membership section: ** Thank you to our sponsors! ** SLNT Visit slnt.com to check out SLNT’s amazing line of Faraday bags and other products built to protect your privacy. As a listener of this podcast you receive 10% off your order at checkout using discount code “sharedsecurity”. **

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The Real State of Offensive Security: AI, Penetration Testing & The Road Ahead with Andrew Wilson is an episode from The Shared Security Podcast by Tom Eston and Scott Wright.

This episode is 44:01 long.

This episode was published on Mar 23, 2026.

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