Women in Cyber: Advice from the Field

Cyber is a notoriously fast-moving field. Adversaries test the limits of our security solutions with threats that evolve by the day. It’s a group effort to fight back and strengthen our digital resilience — featuring tech pros, lawyers, and insurance experts.

Traditionally, this charge has been dominated by men. But thanks to trailblazers in the industry, the tides are turning.

In honor of Women’s History Month, we connected with women across the United States who are making significant contributions to cyber. In our Q&A below, learn more about their career advice, lessons from the field, and visions of a more equal future.

Hear from the women making significant contributions to cyber:

Keeley Sidow

Cyber Practice Director, Woodruff Sawyer

What is your role and how did you end up working in cyber?

I lead Woodruff’s Account Executive and Sr. Account Manager team who are focused solely on advising clients across the country on Tech E&O, Cyber and Media risks. I fell into insurance a couple years out of college through networking connections and started in a Business Analyst role that was not product-specific. I gained exposure to the broad range of commercial insurance products and it was clear to me that Cyber was one of the most interesting and dynamic parts of the industry – I was also pushed that direction by colleagues who I trusted. I’m so thankful that I listened and had the opportunity to get in when I did!

Do you have any advice to share with younger women interested in cyber careers?

Don’t be afraid to go for jobs or projects that you’re interested in and be vocal about it. Don’t assume other people know your goals unless you tell them. Raise your hand even if the opportunity might be a bit of a stretch.  Work on building your network – both within your organization and externally. The insurance industry has so many wonderful, knowledgeable people to learn from and connect with – in cyber specifically and more broadly – be proactive about creating your network.

20 years from now, what advancements would you like to see for women in your field?

I hope there are significant advancements in parental support. We need more women at the executive levels within the insurance industry (and all industries) and continuing to build out a broader infrastructure for long-term parental support will help enable that.  This extends beyond just maternity/paternity leave to continued support as parents work to balance their careers with all the stages of parenthood.  Hopefully, that will facilitate women who want to stay in the workforce to do so – or to come back in after any job pause they may take.

Amanda Mirabile 

Vice President of US Distribution, Corvus Insurance 

What is your role and how did you end up working in cyber?

As the VP of US Distribution at Corvus, my role revolves around strategizing and implementing effective distribution tactics through both traditional and digital channels. My journey into cyber took a circuitous route through various lines of insurance, but the more I learned about cyber the more I became fascinated by how technology-enabled underwriting and risk management can help to add value in what is traditionally a bit of a stale industry. I love that the threat landscape and the way brokers think about this ever-evolving risk means no two days look exactly the same, leaving a lot of room for problem-solving.

Women are more likely to deal with "imposter syndrome". How do you counteract that?

When it comes to imposter syndrome, we are our own worst enemy. I make a conscious effort to celebrate my success, no matter how small. I mean, what can't an iced brown sugar oat milk shaken espresso help solve? Sometimes a little caffeinated pep talk is all you need to show imposter syndrome who's boss.

What are things you've learned from other generations of women, both younger and older?

From younger generations, I've learned that confidence is a super power. It's inspiring watching the younger generation put themselves out there professionally and socially allowing them to build relationships that help them thrive. From the older generations, I've learned that perseverance and resilience paired with trust and compassion are a recipe for success especially when leading a team. After all, without trust, you'll have no influence.

20 years from now what advancements would you like to see for women in your field?

Looking ahead, I envision a future where women in cybersecurity and insurance are not only equally represented, but equally excited to build a career in historically male-dominated industries. Instead of fearing the limits of glass ceilings -- I look forward to seeing them be shattered with style. After all, our unique perspectives and contributions are invaluable in shaping the future of these industries.

Jennifer Beckage 

Managing Director, The Beckage Firm 

Do you have any advice to share with younger women interested in cyber careers?

Embrace the Uncomfortable: A Lesson Learned on the Golf Course. Growing up in Texas, I heeded my boss's advice to learn golf upon high school graduation. "That's where business happens," she said. Today, business isn't confined to the greens, but her message stuck: seize opportunities instead of waiting for them. So, I did and continue to do so. I hope younger women in cyber do the same.

What is one of the challenge you've faced as a woman in the industry?

In life, there are supporters and detractors, celebrants, and betrayers. Yet, amidst the chaos, our self-worth should reign supreme. Let's focus less on external judgments and more on our own integrity. By giving our best in all endeavors, titles, wages, or social validation become irrelevant. Ignore negativity, persist in goodness, and prioritize doing what's right.

What are things you've learned from other generations of women, both younger and older?

In the pre-internet era, influencers were the women who defied the odds, worked tirelessly, and brought about meaningful change. They were the ones we admired and respected for their ability to inspire advancement and hope in others. Today, I draw inspiration from these trailblazers as I strive to disrupt norms in everything I do. From being one of the first tech lawyers, IR and AI lawyers, I aim to echo their legacy of innovation. At The Beckage Firm, the cardinal in our logo symbolizes protection and guidance. Just as we look after our clients, I believe that the trailblazing women who came before me continue to watch over and inspire us to break the status quo. Let's honor their legacy by embracing disruption, learning from the past, and shaping a future filled with progress and equality.

20 years from now what advancements would you like to see for women in your field?

Let's Make a Pact: No More Pantyhose! But on a more serious note, as a mother who has experienced the highs and lows of parenthood – from childbirth to miscarriages, nursing to pumping – I've always been proud to show my dedication to my children while excelling as a lawyer and IR attorney. Yet, I recognize that many still feel hesitant to celebrate parenthood in the workplace. My hope is that in the next 20 years, my daughter and other women, along with parents of all genders, can openly share their struggles and joys of parenthood at work without fear. Let's create a future where parenthood is celebrated and supported in all aspects of our lives.

Marianna Swann

Associate Vice President, Legal and Insurance Vertical at Pondurance 

What is your role and how did you end up working in cyber?

I am the Associate Vice President of the Legal and Insurance Vertical at Pondurance. My first job out of college was selling technology products, professional services and IT infrastructure to Federal, state and local governments. During my 20 year career, I have always been focused on security and compliance. My main objective has been to develop meaningful relationships while helping my customers and partners leverage technology to reduce risk, improve processes, optimize IT & operational resources by becoming a trusted advisor. 

Do you have any advice to share with younger women interested in cyber careers?

I would encourage anyone looking to get into cybersecurity to read a lot about cybersecurity, ask questions, join groups and participate in those groups and to find a mentor. I have been blessed to have some amazing mentors and friends that guided me, supported me, and believed in me along the way. will forever be thankful for those people who are now life-long friends. 

Make sure you surround yourself with a good support system. Great relationships, trusted people in your network, and a supportive family/spouse make a world of a difference while you are working or traveling, as well as when you get home to unwind. 

20 years from now, what advancements would you like to see for women in your field?

I would love to see equality at home and in the workplace. I am lucky enough to have an amazing partner that helps with absolutely everything and anything I ever want or need at home, and I thank my lucky stars that we can pass those values to our children.

In the workplace, I would like to see equality in pay and career advancement for everyone, regardless of race, gender, or disability.

Aisha Robinson

Senior Tech E&O and Cyber Underwriter, Corvus Insurance

Do you have any advice to share with younger women interested in cyber careers?

Mentorship and sponsorship are so important. In an industry that is male-dominated, it may feel hard to navigate. When I started at Travelers in Tampa, the former Managing Director, Anthony Brown, explained the difference of mentorship and sponsorship to me. I think about that conversation to this day because the two sponsors that I had at my time there truly helped me get the exposure that I needed in such a large organization. A mentor is great for the purpose of gaining knowledge, getting encouragement, and some guidance but a sponsor will go to bat for you. A sponsor believes in your future and will help you get in rooms that you never thought you would be in. That kind of advocate is vital if you are looking for advancement. You can be excellent at your role but if your name isn't known you can often be overlooked for opportunities. 

On the other hand, while a sponsor is great, you must also advocate for yourself. There will be moments in your career where you do not have a sponsor at your company so you will be forced to speak up and demand more development, communication, opportunities, compensation, and agency assignments.

What are things you've learned from other generations of women, both younger and older?

One of my mentors, Jennifer Greggs, taught me that you will never have all of the answers. Sounds like common sense, right? In my earlier years of underwriting (like many other underwriters), I felt like if I didn't know the answer to every coverage or control question, I would be seen as incompetent to my agents and underwriting management. Jennifer showed me where to locate resources, how to pin pages, and what to bookmark. She said as long as you know how to quickly access that information, you will be fine in this industry. If you do not have the answer, be honest and say that you will get this to them by the end of the day. 

Also, as you move up, always look back and around you. Lift other women up! You may have a coworker that is interested and capable of doing something that you have knowledge in. Reach out a hand and offer to help them learn or recommend them for a new job opportunity.

20 years from now, what advancements would you like to see for women in your field?

I would like to see more women in leadership roles. In the Cyber insurance space, I have seen more women step into these roles than any other unit in the industry. It is great to see, especially on the broker side. 

Louisa Weix

Managing Partner, TittmanWeix

What is your role and how did you end up working in cyber?

I am the Managing Partner of TittmannWeix a Chambers-rated rated law firm focused on assisting insurers with complex claims. I began working in insurance in 2008 on Tech E&O claims which included Cyber coverages. I have a technical and intellectual property background (having worked for a Swedish company with a trade-secreted beer analyzer, I traveled all over the world testing and tasting beers) and was a big law intellectual property litigator working on high-stakes disputes involving global businesses.  

I loved the analytic challenge and competition. It was exciting!  Now Cyber and AI claims make up 100% of my practice. I am a restless and curious person and the constant evolving nature of cyber makes it a perfect fit for me and for TittmannWeix because of our focus on emerging and novel issues.  

If you get bored easily, cyber is for you.  It moves fast and there is always something new.

Do you have any advice to share with younger women interested in cyber careers?

While there is still an imbalance in insurance generally, cyber insurance is the most inclusive professional community I have been involved in. The support and acceptance are there and wonderful to see. As a lawyer, some of the first “mentoring” advice I received was to add some “niceties” into my email messages and use more exclamation points. Thankfully, those days are in the past.  The new generation of lawyers and insurance professionals are coming into the field more likely to unapologetically assert themselves.  

When I mentor women starting their careers, I advise them to focus on celebrating their successes first and then work on what could have gone better. When you focus intensely on what didn’t go exactly right, it can lead to a misimpression of performance issues. Celebrating wins builds confidence and sends a message of success.  

What are things you've learned from other generations of women, both younger and older?

I have had a chance to work with some amazing women in Cyber and I am still learning from them today. Beth Diamond has been both a client and mentor, especially regarding how to successfully build a team of professionals. I learned to think broadly about qualifications and to bring a diversity of experiences and personalities. My partner Chrtistina Roberto is a great example of the next generation’s ability to forge their own path. She made partner as a fourth year lawyer because she is exceptional and gained the clients’ trust by coming to the table and delivering. Violet Sullivan has been a role model on networking, connecting people, and lifting each other up. And all of the women of the International Women’s Cyber Alliance for creating something from the ground up that connects us together. Brava!

Maggie DePaul

Assistant Vice President of Cyber and Tech E&O Underwriting, Corvus Insurance 

What is your role and how did you end up working in cyber? 

AVP of Cyber Underwriting. I got into the industry right out of college and am one of the weird ones who knew they wanted to get into insurance since they were younger. I have a lot of family in the industry and always saw it as a hidden gem, so it was a no brainer for me. I have even encouraged many friends over the last 8 years to join as well - and many have! 

Do you have any advice to share with younger women interested in cyber careers? 

My advice would be - join us! This is a fun industry to be in with wonderful people, lots of growth opportunity, and it's very dynamic so you'll never get bored. Historically this has been a male dominated industry, so it's been exciting to see more women in recent years. 

What is one of the challenges you’ve faced as a woman in this industry?

Luckily I have not had many challenges in my career solely for being a woman - I have always been surrounded by strong leaders who welcome everyone. So to experience this as well, I would say do your homework when applying to a new job and try to work for and with both men and women who are known to give equal opportunity to all. Then when it's your turn, make sure to embody the same support for all those around you as well. 

Women are more likely to deal with “imposter syndrome.” How do you counteract that? 

When I have imposter syndrome, I remind myself that every person I've ever spoken to has felt that way at some point - even C-Suite level folks. We have all been in the same boat at one point or another and my feelings on this are not unique to me. So keep pushing as everyone else does - you are qualified and you got this!