Ridge Security in the Real World: An Offensive Security Practitioner's Perspective

Ridge Security in the Real World: An Offensive Security Practitioner's Perspective

June 23, 2026 · 59 min · Season 4 · Episode 24

About this episode

Phillip Wylie discusses the future of penetration testing and AI's role in security with Andy Simpson.

## How AI-Powered Penetration Testing Is Transforming Security Validation with Andy Simpson**Sponsored by Ridge Security**In this sponsored episode of The Phillip Wylie Show, Phillip Wylie welcomes Andy Simpson, founder of Cipher Security, for an in-depth discussion about the future of penetration testing, continuous security validation, API security, and the growing role of AI in offensive security.What makes this conversation unique is that Andy is not a Ridge Security employee. As a cybersecurity consultant and penetration testing practitioner, he evaluated multiple automated security testing platforms before selecting Ridge Security to help scale and enhance his team's testing capabilities.Drawing on decades of experience in IT, infrastructure, executive leadership, and offensive security, Andy shares his journey from working at IBM to building a successful offensive security consultancy serving organizations throughout Australia and New Zealand.The conversation explores the challenges facing modern security teams, including expanding attack surfaces, API security risks, infostealer-driven attacks, limited security resources, and the need to continuously validate security…

People in this episode

Host: Phillip Wylie

Guest: Andy Simpson

Topics covered

Keywords

Sponsors

Ridge Security

Mentioned in this episode

Organizations: Cipher Security, IBM

Places: Australia, New Zealand

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