Gary Lobermier on Scaling Red Team Automation with AI to Run Hundreds of Real Attacks Daily

What does it actually mean to validate your defenses continuously?

Gary Lobermier, Lead Adversarial Security Engineer at Northwestern Mutual, built a custom automation platform that runs hundreds of MITRE ATT&CK techniques daily across their environment — and in this episode, he breaks down exactly how and why.

We cover:

- Why Caldera and Atomic Red Team hit their limits at enterprise scale

- The MITRE ATT&CK procedure gap that creates false coverage confidence

- How EDR evasion techniques like DLL sideloading expose what your stack actually misses

- What continuous controls validation does to blue team behavior over time

- Where AI fits — and where it doesn't — in offensive security programs

Gary came up through IT ops before going deep into red teaming and holds his OSCP alongside multiple GIAC certifications. He's a repeat CypherCon presenter and runs GlobeTech LLC as a side practice. This is a practitioner conversation, not a vendor pitch.

This episode is for you if: You're a red teamer, detection engineer, or purple team lead who's hit the ceiling of manual ATT&CK exercises and wants to see what a scaled, automated program looks like inside a real enterprise. It's also worth your time if you came up through IT ops and are building toward offensive security — Gary walked that path and talks about it directly. If you already know what Caldera is and have an opinion about AMSI bypass techniques, you're in the right place.

#OffensiveSecurity #RedTeam #PurpleTeam #PenetrationTesting #MITREATTACK #EDR #CyberSecurity #AheadOfTheBreach

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