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 actorsWhat “AI cloning” really means in a cyber contextHow to design systems that can’t fail, even if users doThe difference between breaking things and building secure solutionsHow to prepare your team with modern, real-world security awareness trainingWhy executives are prime targets — and how to protect themThe limitations of detection tools in a fast-evolving AI arms raceTimestamps:00:00 – Meet Charles Henderson: From hacker to EVP at Coalfire02:00 – Can you just “become” a pen tester? It’s more than breaking things06:30 – The abuse-case mindset: Thinking like an attacker07:45 – AI, social engineering, and the blurry new threat landscape11:00 – Why Coalfire’s team built AI cloning attacks to stay ahead of cybercriminals13:00 – Simple, powerful explanation of AI cloning and pretexting14:00 – Real-world example of AI-based awareness training that worked15:30 – How to redesign systems to limit the impact of human error17:00 – Executive verification: A must-have in today’s landscape18:30 – Deepfake detection tools: Can tech keep up?20:00 – Final thoughts + where to connect with CharlesResources & Links:🌐 Visit Coalfire.com🎧 Subscribe to Cyber Inspiration on YouTube

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