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TL;DR
This is the first article of our Women in Cybersecurity series, in which we’ll explore the careers of women who are making a positive impact in the cybersecurity industry.
In a field once dominated almost entirely by men, the cybersecurity industry is now witnessing a powerful and inspiring shift. Women are breaking through barriers, leading major security initiatives, founding cutting-edge startups, and shaping the future of digital defense. With growing visibility, mentorship opportunities, and intentional efforts to foster diversity, the representation of women in cybersecurity is not only increasing—it's thriving.
From ethical hackers and threat analysts to CISOs and policymakers, women are bringing fresh perspectives, collaborative leadership, and innovation to the forefront. This positive progression isn't just a win for gender equality—it's a strategic advantage for the industry. As we continue to close the gender gap, we’re building a more inclusive, resilient, and effective cybersecurity landscape for everyone.
Our first Women in Cybersecurity article taps into the experience and knowledge of Cybrary’s own Regina Sheridan.
Currently the Director of Content, Sheridan has over 20 years of experience in the cybersecurity field. Her work has taken her from roles at the Department of Defense (DoD) to private sector jobs focused on security awareness, training, project management, and more. Her current role allows her to leverage these experiences while playing to her strengths as a communicator.
This interview has been edited and condensed for clarity.
So how did you get started in cybersecurity?
My story is an interesting one, although not uncommon for someone who began their career 20 years ago. The short answer is, I happened upon an opportunity that led me into cybersecurity. I was working as an administrative assistant. A friend had an opening at her company and asked if I'd be interested in coming to work there. That particular program was a partnership between Computer Sciences Corporation (CSC), which is now a part of DXC Technology, and the DoD Cybercrime Center (DC3). I was hired as an administrative assistant supporting the Defense Computer Investigations Training Academy.
All of this was a really fantastic introduction into cybersecurity because I was in a cyber learning environment, where I got to interact with a lot of instructors and students who came from government, law-enforcement, and DoD-aligned organizations. Being in a learning environment from the beginning was very helpful.
How did you make that jump from being in a good position to absorb a lot of this information to actually being an active contributor?
I had the opportunity to get promoted within CSC to a portion of the company that supported their global infrastructure. The team I was part of was responsible for cybersecurity policy, infrastructure protection, and security awareness training. I found myself supporting both the policy and training components. The through thread with both of those was creating and following cybersecurity policies, and being a good translator of requirements and language from one point of view to another.
Was there a point when you realized that you had a talent for this sort of work? Or was it more subtle?
It was more subtle. I think I just kept saying yes to the right opportunities. When I think back on it now, I'm very grateful I had mentors and colleagues who looked out for opportunities for me to grow. I’ve noticed a difference in how men and women pursue careers. I think women are more likely to disqualify themselves from a position because they don't think they've mastered every part of it. Whereas men, I think, are unafraid to try something that's a little aspirational. Again, I’m grateful I had people who pushed me and encouraged me to go for it, knowing that I would succeed and rise to the challenge.
Could you talk a little more about that? Who have been your mentors? How have they helped you? How did you find them?
Most of the time my mentors have been my supervisors. Especially watching the women around me and how they have thrived in their positions. At DC3, I remember one of the founding members, a woman named Christy Strosnider. Seeing her business acumen and the way she communicated (which was a balance of being very rational, but also being empathetic), and watching how she said “yes” or “no” to the right things in order to stay focused or to pick the right battles, was all very inspiring to me.
In terms of being a minority in this field, did your mentors and this one woman in particular give you advice or demonstrate how to stand out and advance in a place where you might not have the same opportunities as the men you're working alongside?
It was more demonstration than instruction. This is going to sound like a conflicting statement, but I watched them model a balance of being unafraid to speak and also waiting for the right time to jump into a conversation. Learning to withhold my concerns or wait to propose a solution until I had enough data in order to solve the problem has been really pivotal for me. It takes a lot of self control not to jump into a conversation, but to wait to hear all the concerns, understand the underlying root causes, and give a data-driven, emotionally intelligent response.
For example, when I was at CSC, I started coalescing metrics from many different sources to make a unified report, which produced conclusions that couldn't have been seen otherwise because the data was all over the place. I did that for my own curiosity because I wanted to understand how all these pieces fit together. And it turns out I wasn't the only one who benefited from having that aggregate of information in one place. It was very revelatory, and appreciated not only by my direct leadership, but across our business division as well. The report I pioneered ended up being implemented across several parts of the company.
That measure of thoughtfulness and thoroughness I think could be useful advice for plenty of people, not just women. But when it comes to other women, do you have any advice you'd offer them if they want to pursue a career in cybersecurity?
There are multiple threads that have remained true in my career. One is being curious. There's always the role that's on paper, but the requirements to make that role successful almost always involve talking to people who are in different departments or even at different tiers in the organization. So staying curious in order to understand how it all works together is important.
Another is acknowledging weaknesses or mistakes. Not just personal ones, though those are important, but also ones in a process or past project. Just knowing how to pause and recognize that something went wrong so that the team can move forward has helped me out of more than one tough situation. Especially doing so in a kind way, not a combative way. Sometimes, that's all people want to know – that their frustration has been heard and understood.
Finally, staying focused on facts and data. One of my favorite quotes is “Never ignore a gut feeling, but never believe it’s enough.” Women have powerful senses of intuition. I think we can naturally suss out when something is off, or when there’s another point of view that should be considered. That said, the cybersecurity world is filled with very talented, very credentialed experts. A hunch or a gut feeling is not enough to propose an idea or sway a conversation. Seek out the facts and the information, whether that’s in a policy statement or a set of metrics. If you can show compelling data to back up your intuition, other people in the room tend to listen.
Based on your experience, do you have any advice for companies or any opinions about how to keep closing the gender gap that exists in cybersecurity and to keep encouraging more women to enter the field?
It can be as simple as giving people a chance – new folks, and women, and people who don’t appear on paper like they're cybersecurity experts. Opening that door and giving people room to grow is important.
For hiring managers or mentors or teams that want to grow, look for those cyber adjacent skills, knowing that anyone can learn a tool, but you can't teach some of those other personality traits, those other qualities. Look for those who have a willingness to learn, who have creativity and problem solving skills, and have tenacity and the courage to try something even though it might seem one step above them.
Value empathy, value communication, value all those other... I guess they could be called soft skills, but they're just as valuable as any of the so-called hard skills too.
Yeah, or look for people who do more or do a little bit beyond what's stated on the job role. Search out people who want to solve problems with open-mindedness and kindness.
Is there anything else you’d like to add?
I've been fortunate throughout my career to have mentors, leaders, and organizations that believed in me – offering opportunities to grow, explore new challenges, and step outside my comfort zone. A recent example: In addition to my role as Director of Content at Cybrary, I was asked to implement and lead our new “Voice of the Customer” program.
This role has been an incredible chance to blend my background in cybersecurity with my strengths in communication, active listening, and a deep curiosity for data and metrics. It’s all about advocating for our customers, ensuring their voices are heard and that we stay aligned with our mission to deliver a truly exceptional experience.
When I first heard the term “Voice of the Customer,” I wasn’t quite sure what to expect. But as I got into the work, it felt like all the puzzle pieces of my career clicked into place in a really synergistic way. Seeing the positive impact of this effort has been exciting and deeply fulfilling. I know that wouldn’t be possible without a team that values growth, trusts its people, and is open to feedback. I don’t take that for granted.
I love the role I’m in today, and I’m incredibly grateful to be part of Cybrary’s leadership team. My hope is to pay that forward by helping other women recognize their talents, grow in their careers, and feel empowered to make a difference too.
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Are you a woman working in cybersecurity who’d like to share your experience? We’d love to hear from you! Reach out to us at support@cybrary.it.
