Hack My Career: Meet Kayla Underkoffler

In a world where career transitions have become increasingly common, some stories stand out as inspiring. Today, we introduce a remarkable individual who has transitioned from one career to another with unwavering determination and an incredible sense of purpose. Kayla Underkoffler made the remarkable leap from the U.S. military to Senior Security Technologist at HackerOne. Here is her story.

What motivated you to make the switch?

I served in the U.S. military as a musician. Music performance had always been my passion and focus, so when I realized I could serve my country and be a full-time musician as a part of that service, I took up the call. 

After my time in the military, I pursued a business management degree. Through the curriculum, I realized that the theories and skills I was learning had been my constant day-to-day experiences as a leader of the U.S. Marines. I needed a new challenge, especially if I would achieve my goal of being competitive in the job market. I changed my degree to Management Information Systems with a minor in Cybersecurity to facilitate this goal. This is where my technology journey began, and I never looked back. 

How has your non-tech background contributed to your success in the tech industry?

From public speaking to attention to detail, my experiences in performance helped me harness my process for delivering results under pressure. Performing live, whether solo or within an ensemble, is a skill that takes practice to get comfortable with, but in the end, you only get one shot. This has transcended so many areas of my career. 

During my U.S. Marine days, a standout quality that has transferred particularly well into information security is a dedication to the mission. Maintaining the personal discipline and fortitude to commit to the mission and see it through to the end is a required trait for a U.S. Marine. It remains the same in information security, where we defend the mission at hand, and while the mission may look different, the dedication to see it through remains unchanged. 

While in school, I took a summer internship on a security team for a manufacturing company in Pennsylvania, getting my first round of industry-specific on-the-job training. Then, at the end of my school years, I took another internship with a non-profit technology hub for Special Operations Command in Tampa, FL, which morphed into my first full-time civilian career post-college. After a short time there, I had the choice to either pursue a civilian government job or go another direction, which resulted in the magical opportunity to join the Disney team as a security engineer, where I became the subject matter expert for vulnerability scanning for the segment and key player on the Security Operations team. Obviously, I now get to use all the experience and knowledge I’ve gained over the years to serve on the HackerOne team!

How did you overcome challenges?

At Disney, I was a security engineer on the Security Operations team for the Parks and Resorts segment. At a point in my career, my manager voluntold me to pick up the vulnerability scanning focus for the team. This was a scary step in my career transition because I was moving from a relatively hidden support position within the team to a very technical and contentious job that everyone in technology for the whole segment was well acquainted with and often hated and depended upon. 

Let’s just say that if something broke in the environment, all fingers pointed to the vulnerability scanner first and foremost… every time, and when a potential security incident arose, the first question was, “When was the last time that was scanned?” I was always stuck in the middle of providing a mandatory service and being hated for breaking things. 

I was initially afraid of making a mistake. Fearful of breaking something and costing the company real money.

Yet, with all those fears, I powered through and dug into the tool to understand how it works and ensure I represented that tool with professional courtesy everywhere I ran a scan. Over time, this led to a shift in folks' gut reaction when they needed to interact with the vulnerability scanner and me as the operator. 

So, long story long, I was proud of myself for mastering such a technical skill in a pretty short window and turning the attitudes of the cross-functional team members I worked with from strong aversion to trust and teamwork. 

What can you share with those hesitant about a tech career change?

Understand that the world needs a balance of skill sets. We need in-depth subject matter experts – those who spend the entirety of their careers delving deep into a certain subject. We equally need generalists who are technical to a certain degree but who are also organizers, communicators, or big thinkers. There’s no need to pressure yourself to become an expert; combining a non-technical background with the ability to communicate and translate technical content is incredibly valuable. Additionally, the diversity of your experiences, whatever they may be, will create a truly unique portfolio when combined with a new technology future.

Your journey can be as important as the destination. Embrace your individuality and continue to learn and adapt so you can thrive in an ever-changing field, regardless of your background. Thank you, Kayla, for sharing your story and insights into the tech world.