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

<p>AI is making penetration testers faster, but it still cannot replace the judgment needed to prove real business risk.</p><p><br></p><p>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.</p><p><br></p><p>Key takeaways:</p><p><br></p><p>• Learn how AI automates repetitive testing and supports deeper exploit research</p><p>• Compare AI pentesting tools with vulnerability scanners and manual pen tests</p><p>• Judge reports by evidence, repeatable steps, and business impact</p><p>• Understand the privacy risks of sending customer data to public AI models</p><p>• See why hallucinations, scope, and creative testing still need an expert</p><p>• Explore how AI may reshape entry-level cybersecurity career paths</p><p><br></p><p>Follow The Keyboard Samurai and leave a review for more plain-English conversations about cyber, technology, and business.</p><p>Find Nat: https://www.linkedin.com/in/nathaniel-shere/</p><p><br></p>