Career Path - Regan McCooey, Senior Software Engineer II, Technical Lead at EverQuote banner image

Career Path - Regan McCooey, Senior Software Engineer II, Technical Lead at EverQuote

Open Jobs Company Page

What do the career path and the day-in-the-life look like for a Senior Software Engineer II, Technical Lead at EverQuote?

We connected with Regan McCooey to find out!

Interested in learning more about EverQuote and their job openings?  Make sure to check out their company page on VentureFizz!

Where did you grow up?  What did your parents do for work?  

I grew up in Manhasset, NY, a small town on the north shore of Long Island. My Dad worked in Finance on Wall Street when I was growing up and now works as a Real Estate Broker. My Stepmom is a Divorce Coach and helps her clients navigate life changes successfully and my mom works in the healthcare industry. 

Where did you go to college?  What did you study and what were some of your initial jobs out of school?

I majored in computer science at the College of the Holy Cross in Worcester, MA. 

I interned at Credit Suisse as a software engineer the summers following my sophomore and junior years. This provided me with an excellent opportunity to gain experience solving real world problems. Originally, I thought I would begin my career after graduation at Credit Suisse following my internships. However, during my second internship in New York for the bank I realized that software engineering in the Financial industry wasn't the right fit for me at the time and that I wanted to work on solving different types of problems beyond Finance. 

With this goal in mind, I began to look into software engineering roles at large sized technology companies because I knew I wanted a start-up feel paired with an established culture where I could learn and have great mentors. My family friend ended up referring me to TripAdvisor and I interviewed in October of my senior year where I was offered the job. I knew it was a good fit because the people I interviewed with were friendly and it seemed like a very collaborative environment. In addition to the culture and change in industry, I also wanted to work on consumer-facing software that would impact real people which was an added bonus in taking on this role. 

I worked for three and a half years as a Software Engineer (2016-2018) and Software Engineer II at TripAdvisor (2018 - 2020). During this time I learned more than I could ever imagine and my technical skills grew exponentially. After about three years, I still loved coding and solving complex problems so I knew that software was the right path for me. While I enjoyed my role, after a few years I wasn't feeling as challenged as I wanted to be so I started to look for a new job to continue to grow. It was at this point that one of my old colleagues from TripAdvisor messaged me and asked if I was ready for a change and referred me to EverQuote, a insurance tech company in Boston. I ended up interviewing at EverQuote and a few other places but what made me choose EverQuote was that the people seemed awesome and there seemed to be a lot of opportunity to grow from both a technical and a leadership perspective. I’ve now been working at EverQuote on the distribution platform team for two years and it’s been a great experience. I have learned so much and have had the opportunity to solve really difficult problems while working on a replatforming effort, learning about infrastructure in AWS and designing several new systems. 

Regan McCooey Everquote

My team at TripAdvisor: March 2020

What has attributed to your success thus far and has helped propel you to the position you have now?

One thing that has always helped me throughout my career is to constantly learn and improve my technical skills. Growing in the software industry is all about learning new technologies and having different experiences. The software industry is an ever evolving place, where solutions that may be the best way to approach the problem today, might not be the case tomorrow. Whether you’re working on scaling and designing new systems or fighting fires, these experiences will give you more skills and depth in order to enhance and grow your career. 

The more you can remain hungry for knowledge and to constantly learn the more you will succeed. I felt that if I was ever bored it was time for a change or to advocate for myself to get a more difficult or complicated project. You should also never be afraid to try new things and take on a challenge, even if you have never touched that language, technology or design pattern before. New challenges will only help you grow technically in the long run and continue to add to your skillset. 

Also no one is going to advocate for you, you must advocate for yourself. I have channeled this over the past few years by constantly asking for harder and more complicated projects and what I can continue doing or do more of to get me to the next level in my career. If you never ask these questions or have career conversations with leadership you might not accelerate or grow at a pace that you are hoping to. 

Regan McCooey Everquote

My last day at TripAdvisor March 2020

Can you share the high-level responsibilities of your current position as a Senior Software Engineer at EverQuote?

As a Senior Software Engineer II and Tech Lead at EverQuote, I focus on writing code, pairing with other teammates, designing new services for my team and establishing patterns throughout our platform. The distribution platform is the beating heart of EverQuote. Our team runs the main revenue streams of the business and is crucial to the success of the company. In the past year, I have mostly focused on replatforming and designing our new distribution pipeline as well as enabling the business to achieve its goals by designing, planning and implementing new features and enhancements. 

Regan McCooey Everquote

The Distribution Platform Team in our Cambridge, MA office

Any tips for someone considering a career in your field?

A career in software engineering can be very rewarding personally and professionally. The biggest tip I can give to someone starting in the field is to be open to exploring different industries, roles and types of teams to find what you’re interested in. Starting out I had no idea if I wanted to be a front end engineer or a backend engineer. Luckily, I was a full stack engineer that was mostly exposed to backend development, which is the type of software I now prefer. Software is very broad so take the opportunity to be exposed to different technologies, patterns and practices because there are many directions your career can and will go in. 

I’ve also learned that no one knows everything and it’s impossible to be an expert in everything in the world of software. Don’t be intimidated by things you know nothing about. Be curious and add them to your repertoire in order to solve the problem in front of you. 

Day in the Life

Coffee, tea, or nothing?

Coffee - always iced or cold brew even if it’s freezing outside 

What time do you start working? 

I start my work day with a 9 am daily standup meeting

What are three things that motivate you in your role?

  • Solving difficult problems
  • Learning new technologies 
  • Writing code that can be easily built on and changed overtime

Every day is different, but can you outline what a typical day looks like for you?

  • Morning Standup 
  • Pairing with other teammates or meetings related to projects or tech topics 
  • Lunch 
  • Team office hours 1-2 
  • Heads down development time 2-6 

What time do you typically wrap up the work day? 

I try to wrap up around 5:30-6pm each day

Occasionally I will leave a bit earlier if I have plans that night or work a bit later if I am on a roll and haven’t reached a stopping point yet

Do you log back in at night or do you shut it down completely?  

I try to shut down completely. I do go back online if there is an outage of any kind and if I’m on call I work as needed to bring the issue to resolution.

Regan McCooey Everquote

DPLAT’s Trip to Belfast Dec 2021 in our Belfast office 

Any productivity hacks?

I try to block off time each afternoon for heads down time when I can actually code. Having only 30 minutes between meetings is not enough focus time because I need deep focus uninterrupted. I am lucky we work with teams in Northern Ireland so many of our team meetings can be focused in the morning hours and my afternoons are more available to work on code. 

What are the 3 apps that you can’t live without?

  • Google Maps (I have the world's worst sense of direction)
  • Uber 
  • Amazon 

What professional accomplishment are you proudest of?

I have been working with my team on replatforming for the last two years. Seeing that project evolve, take on traffic and start to be the go forward solution for my team’s future has been very rewarding. I’m excited to see our legacy systems retire one by one and be replaced with our new platform which will be easier to maintain, more configurable and flexible than the older systems.  

Who do you admire or call upon for professional advice? 

Several mentors have helped me launch my career. I have had mentors from a combination of sources including managers, senior leaders, and even family friends with related experience. For example, a family friend helped me land my first internship at Credit Suisse and provided guidance that first summer as a software engineer. At TripAdvisor, my family friend referred me and was also on my team for several years. I also had several mentors at TripAdvisor, one being my manager who pushed me to keep challenging myself and trying new things. My colleagues at TripAdvisor are still a great network to lean on, especially as we grew in our careers in different places.

I also lean on my colleagues and leadership at EverQuote to talk about my career path, my goals and what I am looking to work towards as I progress in my career. My manager and many members of the senior leadership team have been instrumental in helping me achieve my goals and continuously develop my skills at EverQuote. 

About the

We are the largest online Auto Insurance marketplace in the U.S. We're helping end distracted driving with our safe driving app, EverDrive.

View Company Page