Women in Cyber: Willa Riggins

In celebration of Women's History Month, we're spotlighting the incredible women of Cobalt throughout March. Each feature will share their unique cybersecurity journeys, insights, and career lessons they have learned.

How long have you been working in cybersecurity? How did you get started in the field? 

I’ve been working in cybersecurity for about fifteen years, and before that, I was in software development, building web applications and batch scripts for data collection. I started my career curious about how things worked, what made them function, and, by proxy, what made them not work as intended. During the interview process for my first part-time job as a junior web developer, they had a practical exam that required you to properly escape user input to prevent SQL injection – and I failed it. To be fair, I learned PHP over the weekend for the interview, but thankfully, they hired me anyway and taught me how to canonicalize user input properly. That really launched my interest in cybersecurity and would lead me to eventually jump from developer to security engineer to red team operator. 

What has been the greatest reward of your career? What do you love most about your job? 

Prior to Cobalt, I spent close to six years managing teams of penetration testers both in a consulting firm and on an internal team. The greatest rewards in my career have been watching my team members grow. Hiring people with talent who just needed a chance to show their skills and then rewarding them for their awesome work was something special. Seeing hackers light up with joy when they exploit that mainframe for the first time or when they exploit that LFI and escalate to root – that’s just a great feeling. 

What has been the greatest challenge you faced in your career? 

Honestly, the biggest challenge for me has always been finding the right fit. This industry is remarkably small and connected, but it can be difficult to land in a spot where you can grow, learn, and have fun doing it. When you find the right group of people who care about what they do, who they do it with, and how they get there – that’s something to hold on to. There are people I’ve worked with in the past who stick together for that reason alone, and many of us have worked to build those communities in other organizations, too. 

What impact has female mentorship had on your life? Was the impact in a personal or professional setting? 

I’ve had several mentors over the years, but one took me under her wing and taught me everything about how a consulting practice runs. She took a chance based on our work together at a prior company, and knew that I had technical ability, but I’d never been responsible for entire service lines or contracting. Learning the business side of the practice really set me up for success down the line, and launched my career in a new direction. I’d say our mentorship started in a professional setting, but we quickly became friends and stay in touch to this day. 

What is your advice to young female professionals coming into the workforce or into cybersecurity? 

Be curious, learn as much as possible, and find what you love doing. You’ll always be more effective, driven, and passionate about something you care about, and that will drive your career to new heights. Network, but do it in a way that adds value for yourself and the community. Volunteering at local BSides events, teaching at student events, or just getting involved in your local OWASP chapter or DEF CON group can make networking less rote and more meaningful. 

What’s your biggest inspiration or motivator when you are down? 

My family definitely helps here, as my wife and kids always keep me motivated and inspire me to focus on what really matters. That and my cats. Have you ever hugged a fluffy kitty and nuzzled into their cute little face when you’re sad? It's 100% effective. It works every time.

Is there a moment in recent memory, where you felt empowered by female representation?

This is going to sound trite, but during my interview process here at Cobalt one of my interviewers mentioned that I’d probably be happy to know how diverse the company was. I didn’t think much of it as I’d interviewed with quite a few organizations who talked a lot about their resource groups and initiatives, but I didn’t realize until my first week how much Cobalt really embodied it. It’s been rare for me to be the only woman in a meeting here, and there are women at every level of the organization making an impact at the company every single day. It’s been refreshing, and I’m just excited to work with all these amazing women! 

Learn More About Willa 

What are your favorite hobbies?

I love birding, wildlife photography, PC gaming, and playing D&D.

Who are your favorite musical artists? 

Caravan Palace, OK Go, or Snail’s House!