Kayla Underkoffler

Kayla is a lead security technologist with HackerOne and is currently the team lead for the Internet Bug Bounty program.

Kayla spent four years as a United States Marine in the Quantico Marine Corps Band, before leaving active duty to pursue a career in Cybersecurity. She landed the magical opportunity to work on the security team for the Walt Disney company in the Disney Parks, Experiences and Products segment as a vulnerability management lead. With a passion for bridging the gap between business and technology, Kayla continues to evangelise the importance of security for everyone.

Tell us a bit about yourself, background and your current role:

I left for United States Marine Corps Bootcamp on a Sunday, after graduating from high school the day before. I spent four years as an active duty Marine in the Quantico Marine Corps Band, as a bassoonist and administration lead. After my enlistment, I decided it was time to explore another career field. I discovered Information Security during my time as a student at the University of Tampa, where I majored in Management Information Systems and earned my minor in Cybersecurity. After graduating, I worked with United States Special Operations Command and then with Disney as a hands-on technical and security lead.

Today, I’ve had the opportunity to bridge my experience as a security practitioner with business strategy as Lead Security Technologist with HackerOne. I am the program lead for the Internet Bug Bounty – a bug bounty program built specifically to support the critical shared open-source software we all depend on. I also have had the opportunity to contribute to international security policy and standards where I often help distill security topics for the masses and evangelize the importance of security for all.

Did you ever sit down and plan your career?

Yes! My plan was to be a professional musician! I was going to major in bassoon performance. However, the details of how I would actually put that major to use became a bit blurry. That’s why I joined the Marine Corps, to become a professional musician with a clear mission and career as a Marine. After I decided to move on from active duty I thoroughly planned my higher education journey, but changed my major to be more focused on technology mid-way through. This allowed me to be strategic with internships and follow-on career opportunities in a field that has focus, but also many channels with a variety of practices and specialities. So, long story long, I’ve always been a planner, and those plans have always changed, but it makes me feel better to have something written down anyway.

Have you faced any career challenges along the way and how did you overcome these?

My biggest career challenge in the technology field actually appeared during my time in school. After making the transition from a non-technical background of business management to the more technical route of management information systems, I felt behind compared to my classmates. I had this picture in my mind that everyone else in class had been playing around with computers since they were little kids, and I hadn’t. In reality, this was just imposter syndrome typing in all caps in my head. I overcame this perception that I was behind by capitalizing on the skills I brought to the table and then put real effort into my studies. I quickly learned that the gap I perceived in my mind was just that, in my mind. I was just as capable of understanding and implementing technical skills as anyone else in my class. I’ve carried that belief in my ability to adapt to and quickly learn technical topics into my career today.

What has been your biggest career achievement to date?

Taking on a technical role was not exactly what I had envisioned when my manager sent me down the vulnerability scanning road. But, in hindsight, that move was the best thing for my future. I worked within vulnerability management for 3 years, and by the end of that time I was the subject matter expert on my team. My biggest achievement to date has been navigating the transition from that hands on security role to a strategy focused role. For me, it was intimidating and out of my comfort zone to walk away from being the expert to taking on something completely new! But when the right opportunity with HackerOne presented itself, I was able to take those hard learned skills from my previous role and apply them within content creation, education, and messaging for HackerOne’s business. This has been another pivotal shift in my career, and I’m proud that I was able to make the leap and stick the landing.

What one thing do you believe has been a major factor in you achieving success?

I would consider tenacity the driving force in my career. I am tenacious in my pursuit of all things. I believe in what I produce, and I have the highest standards for myself. This determination allows me to put pride and fear aside to do whatever is necessary to get things right. If I have to ask for instruction or clarification, if I need to object to something, if I have to learn something new or present in front of others, I’ll do what I need to because I want any product I release to be something I can be proud of. Tenacity keeps me in relentless pursuit of higher standards.

What top tips would you give to an individual who is trying to excel in their career in technology?

Take a page from my experience, and don’t dismiss your ability to master a technical skill. Today, performing or even just understanding technical topics is powerful when combined with soft skills. Being able to connect with people and tell a story is just as important as being able to technically perform a task. It’s often said, and I do agree, that technical skills can be learned; it’s much harder to learn the people skills to connect and share a story that takes someone on a journey. If you can do both, you’ll be in limited company, and highly valued talent.

What barriers for women working in tech, are still to be overcome?

One of the main barriers for women in tech is the lack of structured, work-sponsored opportunities to learn and excel in a new technical role. Learning a technical skill in a siloed fashion, so at home or in your free time, is still removing barriers for women in tech. However, a more efficient way to get women into technical roles, and to ensure their success, is to facilitate formal lateral role transition programs. The format of the transition works best when there is access to a training program part time and part time shadowing for on the job experience. The best way to learn a skill and make it stick is to actually perform the work on a daily basis, and just going through an outside of work training program only gets someone half the way there. If more companies offered the opportunity for women to transition from a more business oriented role to a more technical role with education and support provided, more women would have an opportunity to bridge into technical roles.

What do you think companies can do to support and progress the careers of women working in technology?

Outside of more formal, on the job technical training opportunities, another truth is that to support progress for women’s careers there needs to be better support for families built in. This often comes in the form of flexibility. For those who choose to start families during their careers, or maybe they’ve come into a career with a family, dedicating 100% effort and attention to a job with no flexibility is often not feasible. More importantly, it should never be expected. As a mother of two, I am more than grateful for HackerOne’s support of employees with families. Never once did I question my ability to continue to grow my career after starting my family. That support will make all the difference for many women being able to reach leadership roles or even highly technical subject matter expert roles.

In an ideal world, how would you improve gender diversity in tech?

Gender diversity in tech needs to start young. Young girls in school need to be provided all the opportunities to learn hands-on technical skills that any of their classmates do. They need to see grown women in these fields to have that inspiration through representation. This means that to improve gender diversity in tech, we women in the field need to get out more. Get involved with local schools and extracurricular activities. Be a part of your community. Be the example these young ladies can aspire to. The more we can directly foster the community the more diverse it will become.

Read more from our inspirational women here.