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
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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
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The Cyber Circuit is powered by Insight Jam
Visit https://insightjam.com to join the human conversation around AI.
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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
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
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