Insight Jam

Red Teaming in the Age of AI - The Cyber Circuit

What happens when the attackers start using AI faster than the defenders can keep up? Robert Pimentel @HackerHermanos, joins Michael Morgenstern to explore how AI is transforming offensive security operations. Robert breaks down his three-pronged approach to AI-augmented red teaming, from accelerating pre-operation setup and mid-operation enumeration to generating high-quality reports in minutes. He shares real metrics on what AI-assisted teams are producing compared to traditional workflows. The conversation also tackles the future of the profession, the skills that will separate high performers from "slop cannons," and what red team leaders should be prioritizing in the next 18 months. Subscribe to the Insight Jam channel for more and sign up for our newsletter, The Human-AI Ledger: https://bit.ly/HumanAINewsletter ************** Robert Pimentel https://hackerhermanos.com/ https://linktr.ee/hackerhermanos https://www.todosec.com https://linkedin.com/in/pimentelrobert1 https://linkedin.com/company/HackerHermanos ************** Michael Morgenstern https://www.linkedin.com/in/michaelimorgenstern/ https://dayblinkconsulting.com ************** The Cyber Circuit is powered by Insight Jam Visit https://insightjam.com to join the human conversation around AI. ************** 00:00 Introduction and Guest Welcome 02:06 AI Red Teaming vs Red Teaming with AI 07:00 Nation State Threats and the Scale of AI-Augmented Attacks 09:10 The Productivity Metrics That Will Keep Blue Teamers Up at Night 13:15 Contextualizing Findings and Augmenting Report Quality 15:25 Scanning Millions of IPs and Using LLMs as Judges 19:01 AI as a Force Multiplier Before and During Operations 26:05 Closing Out Operations and Briefing Leadership at Scale 34:00 The Role of Physical Security in an AI World 36:10 Where Red Teaming Is Headed in the Next 18 Months 46:03 Outro and Guest Links