Episode 86
Episode 86 - Charles Henderson - EVP of Cyber Security Solutions at Coalfire
In this episode of Cyber Inspiration, host Evgeniy Kharam sits down with Charles Henderson, Executive Vice President of Cybersecurity Solutions at Coalfire, to explore how artificial intelligence is reshaping the cyber threat landscape.
From AI-driven impersonation attacks to the ethics and implications of deepfake technology, Charles shares firsthand insights from the frontlines of offensive and defensive security. Whether you’re a CISO, red teamer, or simply want to understand how threat actors are exploiting AI, this episode will challenge your assumptions and sharpen your awareness.
What You’ll Learn in This Episode:
- Why AI is becoming the go-to tool for threat actors
- What “AI cloning” really means in a cyber context
- How to design systems that can’t fail, even if users do
- The difference between breaking things and building secure solutions
- How to prepare your team with modern, real-world security awareness training
- Why executives are prime targets — and how to protect them
- The limitations of detection tools in a fast-evolving AI arms race
Timestamps:
00:00 – Meet Charles Henderson: From hacker to EVP at Coalfire
02:00 – Can you just “become” a pen tester? It’s more than breaking things
06:30 – The abuse-case mindset: Thinking like an attacker
07:45 – AI, social engineering, and the blurry new threat landscape
11:00 – Why Coalfire’s team built AI cloning attacks to stay ahead of cybercriminals
13:00 – Simple, powerful explanation of AI cloning and pretexting
14:00 – Real-world example of AI-based awareness training that worked
15:30 – How to redesign systems to limit the impact of human error
17:00 – Executive verification: A must-have in today’s landscape
18:30 – Deepfake detection tools: Can tech keep up?
20:00 – Final thoughts + where to connect with Charles
Resources & Links:
🌐 Visit Coalfire.com
