How Did You End Up in Insurance? Spotlight: Jay Frey, Root Insurance

3 Comment(s) | Posted |

Jay FreyThere are many different paths that can be taken that lead people to insurance careers. We decided to reach out to a local insurance professional, Jay Frey, of Root Insurance, and ask, “How did you end up in insurance?”. His story is inspiring and shows that no matter your background, insurance could be a great fit for you!

Past Careers

Growing up and into his early twenties, Jay worked as a lifeguard and swim instructor. He then moved on to try some college and decided it was not him. His next career move involved manual labor jobs. He attended the Universal Technical Institute to learn how to work on cars. After completing the training and working on cars for about one and a half years, Jay realized this was not what he wanted to do for the rest of his working life. He realized manual labor was hard on his body, and the industry did not provide much opportunity for growth or income increase. He knew there had to be a better career fit out there for him.

The Shift to Insurance

A pivotal moment in Jay’s career journey was when he decided to pursue his degree in accounting. He had family members who had worked in accounting and saw potential in pursuing that career path. He continued to work and completed his degree through Franklin University at night, and was able to quit his job fixing cars.

Through connections he made with a classmate at Franklin, he scored a job doing entry level accounting at a property management company. This role included doing AP bill coding, premium taxes, and accruals. The management company he worked for was bought out and relocated. However, prior to their move, he was able to get a bonus, step up, and learn more than the regular entry level skills before the end of his time there.

Shortly after that door closed another one opened with State Auto Insurance. His role was doing reinsurance accounting. He knew nothing about the insurance industry and knew no one in the industry.

“I would say that getting that job at State Auto was easily the biggest moment of my life and changed the trajectory of my career and earning capabilities.” Jay said.

He remained at State Auto for five years learning a lot about both ceded and assumed reinsurance accounting. He then spent a year at Nationwide doing life statutory reporting before returning back to corporate reinsurance accounting. During his time at State Auto and Nationwide, he took tests from The Institutes and received  four different designations and even went on to earn his masters in Risk Management from Florida State.

How He Started at Root

A year ago his first boss at State Auto reached out to ask him to join the team at Root Insurance as the main reinsurance accountant. He jumped at the chance to work with his old boss again, and the CFO of Root who he also had worked for at State Auto. He leveraged his insurance knowledge to become a part of capital strategy and has led the team that books all direct, ceded and assumed insurance transactions.

Root offers an engaging work environment and the freedom of no dress code, free lunches and snacks, and free benefits. Jay said, “Now I have the most amazing job at a company I truly believe in! My favorite thing about working here is that Root truly lets you be the person you are. I would say that I am not the most “traditional” insurance accountant and I feel so comfortable here at Root. It has allowed me to cement my accounting knowledge while opening up so many new opportunities for my career. I wouldn’t want to work anywhere else!”

Why Insurance?

Jay shared some of the best parts of working in the insurance industry…

  • Stability and job security due to his specialization
  • The fact that the industry is always changing
  • The friends and professional connections he has made through the tight knit insurance accounting community
  • Career trajectory and earnings are higher in the insurance industry versus other accounting careers
  • From his experience, insurance companies treat their employees well

“If someone is looking to switch careers to the industry I would say this- do it!” Jay said. His main piece of advice he shares with newer insurance professionals is to take the tests and get the designations from The Institutes and do it early in your career. He said the learning curve in the insurance industry is steep and those tests, along with learning more about the industry as a whole, give you a solid foundation to build on and are critical to success.

Learn more about how you can get on a fulfilling and successful career path like Jay did! Check out our resources on


  1. Caitlyn Berg's avatar
    Caitlyn Berg
    | Permalink
    So happy to have you at Root, Jay! You are a great addition to our team and we are lucky to have you.
  2. Carolyn Schaeffer's avatar
    Carolyn Schaeffer
    | Permalink
    It was such a pleasure to work with you at Nationwide. I’m happy you found a home at Root. Best of luck to you!
  3. Pete Love's avatar
    Pete Love
    | Permalink
    Congrats Jay - nice article and glad to hear you enjoy your career! Happy for you!

Leave a Comment