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…