Meet Alumna Regan McCooey ’16, Senior Software Engineer at EverQuote

Name: Regan McCooey

Class Year: 2016

Title: Senior Software Engineer

Organization: EverQuote


1. In one sentence, what does your job entail?

I design and implement backend services that facilitate the auction and distribution mechanics of EverQuote’s insurance marketplace.

2. What planned and unplanned events connected you to your industry and your first employer after Holy Cross? How did you learn/decided it was a good fit for you?  

After my sophomore and junior years at Holy Cross, I interned at a bank as a software engineer. Originally, I thought I would end up working there; however, after my second summer, I realized that software engineering in finance wasn’t the right fit for me. I began to look into software engineering roles at larger tech companies. My family friend suggested that I apply to TripAdvisor. I interviewed in October of my senior year and was offered the job. I knew it was a good fit because the people seemed very nice and the culture was exactly what I was looking for. I also wanted to do more consumer facing software that would impact real people rather than just writing programs for the back office of a bank.

I spent 3 years as a Software Engineer at TripAdvisor. I learned more than I could ever imagine and my technical skills grew exponentially. I still loved coding and solving complex problems so I knew software was the right path for me, for now. After a few years at TripAdvisor I wasn’t feeling as challenged as I wanted to be so I started to look for a new job. One of my old colleagues from TripAdvisor messaged me and asked if I was ready for a change, and referred me to EverQuote. I ended up interviewing at EverQuote and a few other places. What made me choose EverQuote was the people seemed awesome and there seemed like a lot of opportunity to grow from a technical and a leadership perspective

I started at EverQuote at the end of March. It’s been great so far! It’s definitely been a challenge remotely onboarding and learning everything without being face to face with your teammates but I’m learning a ton and I know it was the right move for me.

3. What were you involved in when you were on campus?

I played varsity golf for two years and was on the ski team. I participated in Big Brothers Big Sisters as a mentor, acted as an officer for the Math and CS Club, and was a teaching assistant for computer science.

4. What was your major and how did it affect your career decisions?

I majored in computer science. The classes I took at Holy Cross inspired my love of programming, and helped me decide to pursue a career as a software engineer. When I took Compiler Construction, an upper level project course that involved a lot of programming, I knew that I wanted to be a software engineer.

5. What are one or two skills that you developed at Holy Cross that you use in your work?

Besides teaching me how to program, Holy Cross taught me to adapt and to teach myself the skills necessary to solve the new problems I encounter every day. The software industry is very fast paced. Things are constantly changing and you are expected to adapt and learn fast. Working in the industry is also very different from programming at school. Nevertheless, the various projects I completed in my computer science courses challenged me to face the problems in front of me head-on and to find creative solutions. My Holy Cross experience gave me the confidence to take on the new challenges I face every day as a software engineer.

6. What advice do you have for students on campus today?  

I would tell current students that they should never feel unqualified or unable to do a job because they don’t have all of the qualifications listed on a job advertisement. Job postings usually have an intimidating list of qualifications, especially in the software industry. If a student meets even one of those qualifications, they should apply for the job. Holy Cross students should always feel confident that they will be able to learn the specific technology required on the job. Prior to starting at TripAdvisor in 2016 and EverQuote this year, I barely knew the programming languages I use everyday. Also I barely knew how to deploy a service using Amazon Web Services, but I figured it out and was able to help create a deployment pipeline for my team. It’s not about what you know or don’t know now, it’s about how you can adapt yourself to learn what you need to know to succeed.