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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 paths
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Find Nat: https://www.linkedin.com/in/nathaniel-shere/
