Nat Shere — AI Didn’t Kill Pentesting. It Made Judgment More Valuable.

AI is making penetration testers faster, but it still cannot replace the judgment needed to prove real business risk.Wil hosts Nat Shere, Product Security Manager at Skillable and a penetration tester with more than 10 years of experience, for a practical look at AI penetration testing. They break down where AI helps, where automated pentesting falls short, and why finding more vulnerabilities does not matter unless a tester can prove exploitability and impact. This episode is for CISOs, security leaders, buyers, and cybersecurity professionals trying to separate useful AI tools from expensive scanner theater.Key takeaways:• Learn how AI automates repetitive testing and supports deeper exploit research• Compare AI pentesting tools with vulnerability scanners and manual pen tests• Judge reports by evidence, repeatable steps, and business impact• Understand the privacy risks of sending customer data to public AI models• See why hallucinations, scope, and creative testing still need an expert• Explore how AI may reshape entry-level cybersecurity career pathsFollow The Keyboard Samurai and leave a review for more plain-English conversations about cyber, technology, and business.Find Nat: https://www.linkedin.com/in/nathaniel-shere/