In this episode of the Chasing Entropy Podcast, I speak with Mark Hillick, CISO at Brex, about the changing role of security leaders in a world shaped by AI, rapid innovation, and shifting business expectations. From building security culture at Riot Games to navigating Silicon Valley’s AI gold rush, Hillick offers grounded insight into what it takes to lead a modern, business-aligned security team.

1. Security as a Business Enabler

Hillick shares his journey from infrastructure engineer to CISO, emphasizing that the best security teams don’t just protect—they enable. By integrating early, communicating clearly, and avoiding gatekeeping, security becomes a trusted partner, not a blocker.

“If the business isn’t there, we wouldn’t be either. Security must enable, not obstruct.”

2. The Role of Empathy and Trust

Drawing from his experiences across industries and geographies, Hillick highlights how trust is built—and lost. He discusses the trauma some teams bring from past negative security experiences and why empathy and explicit communication matter more than ever.

3. AI: Hype, Hope, and Risk

Hillick identifies AI as the third major paradigm shift of his career. He outlines how AI is reshaping internal productivity, operational efficiency, and product development—but warns that many organizations are repeating old security mistakes by moving too fast without proper safeguards.

“If you’re a security engineer and not using tools like Copilot or Cursor, how can you help others use them securely?”

4. The Sales Dilemma

Dave and Mark discuss the fine line between outreach and overreach in cybersecurity sales. Hillick shares candid stories—from being bombarded with cold calls to salespeople contacting his spouse—and makes the case for respectful, empathetic sales practices.

5. Advice for the Next Generation

For those entering the field, Mark keeps it simple:

Show up.
Work hard.
Stay curious.
Be kind.

“Curiosity will protect you from cynicism. And this industry needs a lot less cynicism.”

This episode is a must-listen for security practitioners, leaders, and anyone curious about the future of cybersecurity leadership in the age of AI. It’s a real, unfiltered conversation—minus the FUD, plus a healthy dose of dry humor.

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Link: https://www.buzzsprout.com/2497520/episodes/17430216-chasing-entropy-episode-010-empathy-ai-and-the-evolution-of-security-with-mark-hillick

If You’re a Sales Rep, Listen to This Before It’s Too Late