Organised by Eskenzi PR in media partnership with the IT Security Guru, the Most Inspiring Women in Cyber Awards aim to shed light on the remarkable women in our industry. The following is a feature on one of 2024’s Top 20 women selected by an esteemed panel of judges. Presented in a Q&A format, the nominee’s answers are written in their own words.
In 2025, the awards were sponsored by BT, KnowBe4, Mimecast, Varonis, Bridewell, Certes, Pentest Tools and AI Dionic. Community partners included WiCyS UK & Ireland Affiliate, Women in Tech and Cybersecurity Hub (WiTCH), CyBlack and Inclusive InCyber (LT Harper).
What does your job role entail?
As Chief of Staff for Microsoft Red Team, I drive the strategy behind how we innovate and evolve red teaming—transforming it from purely technical operations into a strategic security pillar that directly shapes Microsoft’s overall security direction. My role is to define what modern red teaming looks like—not just for Microsoft, but for the industry—as this space rapidly evolves.
Microsoft is pioneering and reimagining how red teams operate in this new era, ensuring that every finding leads to measurable, lasting fixes. With the rise of AI and the Security Graph, we are shifting from product-based technical assessments to precision-driven security, uncovering micro-level vulnerabilities that could have massive impact. I also lead the vision for extending red teaming beyond human limitations, not only within Microsoft but across our customer ecosystem, helping to shape the future of collective defense. This includes driving strategies to accelerate remediation and push toward a self-healing security model—where threats are dynamically identified, understood, and resolved at scale.
How did you get into the cybersecurity industry?
I never set out to work in cybersecurity—I stumbled into it by accident. But looking back, I realize I’d been preparing for it all along. After leaving my small town in Bulgaria with just $50 and a dream for something bigger, I spent years relentlessly building my tech skills, working nights in restaurants and weekends for free on small tech projects just to prove myself. I was exhausted, broke, and doubted myself constantly. There were so many moments I almost gave up. But I didn’t.
And then, one day, cybersecurity found me. An unexpected opportunity appeared, and even though I felt unqualified and terrified, I took the leap. That leap changed everything.
Cybersecurity became the perfect place for my grit and curiosity to collide—a field where I could protect people, solve complex problems, and make a real impact. Today, I lead strategy for the Microsoft Red Team, helping shape the future of red teaming not just for Microsoft, but for the entire industry.
If my story proves anything, it’s this: you don’t have to see the whole path. You just have to keep going. Keep building. Keep believing. Because sometimes the thing you never planned for becomes the thing you were born to do.
What is one of the biggest challenges you have faced as a woman in the tech/cyber industry and how did you overcome it?
One of the biggest challenges I faced as a woman in cybersecurity was overcoming deep imposter syndrome—believing I didn’t belong in the room. Coming from a small town in Bulgaria with no role models in tech, I carried years of conditioning that told me success in this field wasn’t meant for people like me. Early in my career, I often felt like I had to blend in—dressing, speaking, and acting like the men around me just to be taken seriously.
What helped me overcome it was realizing that my unique story, my perspective, and my authenticity are exactly what make me strong. I found inspiration through the few women ahead of me who owned their space unapologetically, and they helped me see what was possible. Now, I make it my mission to be that example for others—showing women that we don’t have to change who we are to succeed in cybersecurity. We belong here exactly as we are.
What are you doing to support other women, and/or to increase diversity, in the tech/cyber industry?
I’m deeply committed to helping women and underrepresented groups break into cybersecurity and thrive. Over the years, I have served—and continue to serve—on various leadership boards and advisory groups to help shape the future of the industry and drive meaningful community impact. This includes organizations like OWASP Seattle, the EC-Council Certified Ethical Hacker (CEH) Advisory Board, Women in Cybersecurity (WiCyS), and ISACA Puget Sound.
As Co-Founder of Women in Tech Global and a leader in Microsoft Women in Security, I’ve helped build global communities that give women access to career opportunities, speaking platforms, and technical growth.
I also actively mentor young women, guiding them through career transitions, helping them overcome self-doubt, and supporting them as they step into leadership roles they may not have thought possible.
Beyond mentorship, I’m passionate about modernizing cybersecurity education. Through projects like The Hacking Games, I’m helping inspire the next generation of diverse talent by reimagining how we teach ethical hacking to Gen Z.
For me, this work is personal. I know how hard it is to build a path where none exists. That’s why I’m committed to being the example I wish I’d had—and ensuring no woman feels like she has to do it alone.
Who has inspired you in your life/career?
I’ve been most inspired by the women who dared to take up space in rooms where they were never expected to belong—and did it unapologetically. Seeing strong women lead in cybersecurity with both confidence and authenticity showed me that we don’t have to trade our uniqueness to succeed in this industry. Their example helped me realize that my story, my background, and even my struggles are my power.
But beyond individual people, I’m inspired by the millions of women who haven’t yet been told they belong here. I think of the little girls staring out of windows in small towns, just like I once did, wondering if there’s more to life than what’s been handed to them. They inspire me to keep going, keep building, and keep showing up—because if I can be proof for even one of them that a different future is possible, then every challenge I’ve faced was worth it.
We need more examples to emulate—more women leading, succeeding, and owning their space—so others can see themselves in us. That’s why what we’re doing here is so important. Visibility creates possibility. And together, we’re redefining what’s possible for the next generation.
The post MIWIC25 – Eva Benn, Chief of Staff, Strategy – Microsoft Red Team appeared first on IT Security Guru.
