SecOops - Almog <> Yossi Sassi

In this edition of SecOops, I sat down with Yossi Sassi, our Chief H@ck3r at TandemTrace, to discuss his journey in cybersecurity, the lessons learned from failures, and where he sees the industry heading with the rise of AI-powered security.

The Journey

Almog: Yossi, you’ve been in cybersecurity for over two decades. What drew you into this field?

Yossi: Honestly, it was the puzzle aspect. In the late ’90s, I was fascinated by how systems could be broken and protected at the same time. Every vulnerability was a mystery to solve, and every exploit was a lesson in how software really works beneath the surface. That curiosity never went away—it just got more sophisticated as the threats evolved.

On Failure and Learning

Almog: You’ve talked before about the importance of failure in security. What do you mean by that?

Yossi: In security, you learn more from what breaks than from what works. Every successful breach teaches us something new about attacker tradecraft. Every missed detection reveals a blind spot in our defenses. The organizations that treat incidents as learning opportunities—that do thorough post-mortems and actually change their processes—those are the ones that get stronger over time.

The worst thing you can do in security is pretend you’re invulnerable. The best defenders I know are the ones who assume they’re already breached and hunt accordingly. That mindset, that healthy paranoia, comes from understanding how often defenses fail.

AI’s Role in Security

Almog: Now you’re working on AI-powered threat hunting. How do you see AI changing the security landscape?

Yossi: AI doesn’t replace human expertise—it amplifies it. The threat hunting techniques I’ve developed over twenty years, the patterns I recognize, the intuition about what “feels wrong”—we can encode that into AI agents that can apply those same principles continuously across massive amounts of data.

What excites me is democratizing expertise. Not every organization can hire a team of elite threat hunters. But they can deploy AI agents that embody that knowledge and hunt on their behalf 24/7. That levels the playing field in a way that’s never been possible before.