Agent Spotlight: Ashley Rosborough, ACSR, CIC, J.T. Rosborough, Inc.

Ashley Rosborough, ACSR, CIC

Agency Manager & COO, J.T. Rosborough, Inc.

J.T. Rosborough’s Agency Manager and Chief Operating Officer, Ashley Rosborough, returned home to downeast Maine in 2010 – and joined the family agency – using business acumen honed by marketing and public relations experience with the American Hockey League’s Portland Pirates and various radio groups in Portland, ME and Laconia, NH. A graduate of the University of Southern Maine, she has worked her way up from a CSR in Personal Lines and joined the ownership group in 2017. “Over the years I slowly became more involved with the relationships with our companies and operations management within the agency,” she said. “When I knew I wanted to move back to downeast Maine for good, my uncle and dad gave me the opportunity to try working at the agency. It wasn’t something I grew up thinking I would go into, but I am so glad it was in my family and that (after working elsewhere) I gave it a chance. I truly love my job and our business.” It is that drive to build and nurture relationships, along with a love of problem-solving, that has guided Ashley’s career to the heights she has earned today.

Why have you stayed in the industry? I really love how challenging and dynamic the work we do is. The problem-solving aspect and never knowing what your day will look like or what the next risk will be like to work on is exciting to me. You meet the most interesting people and learn so much about such a wide range of things people do as business owners it’s really fascinating.

I also love the people you interact with that also work in the insurance industry. I have made some of my best friends through various professional groups and have had some great times while participating in networking events and educational/ leadership conferences.

Why should people consider a career in insurance? There is so much opportunity and such a broad spectrum of jobs within insurance that can relate to almost anything someone is interested in. We are so fortunate to work in an industry that will never go away. It will continue to evolve as the world and risks change, but there will always be a need and job security because of that. We saw how resilient the industry was when having to adapt during the beginning of the pandemic, and there is a lot to be said for that. Plus, for something that sounds so dull, we all manage to have a lot of fun.

What is a misconception about insurance/an insurance career that you want to clear up? A couple things come to mind:

  • That it’s boring. As I said things are always changing and no two days are the same. You are constantly learning and interacting with fun people and being challenged in a variety of ways.
  • That you need some sort of prior training or knowledge to work in the industry. Most people know very little even about their own policies when they first start out, everyone has to start somewhere. If you have the right personality and attitude, you can easily be very successful in insurance.

What is the most used tool/resource that has made you the most successful? Networking and getting involved in professional groups and serving on boards for community organizations is the biggest resource I have utilized by far. Not only joining as a member of these organizations, but also being a vocal, active participant.  I have made sure to seek out and take opportunities to meet new people inside and outside of the industry whenever possible and it has made me a more well-rounded, dynamic professional. Doing these things has allowed me to learn from others and has put me in front of people I never would have had the opportunity to otherwise. It has given me the chance to show my knowledge, personality and how I approach the business, in turn attracting people who want to work with me.

What is the most important leadership lesson you have learned, and how is it valuable to you today? Don’t get distracted by what others are doing or what others think of you. The old adage, “what someone else thinks or says about you is their problem,” is very true. If you work hard and are doing the best you can for your employees and clients then you have nothing to worry about. 

What professional organizations are you associated with and in what ways? For many years I was a member of the MIAA (Maine Insurance Agents Association) Young Agents Committee – now a former committee member and served as Chairwoman. I really attribute so much of my success to the connections and opportunities I developed through being involved with the Young Agents. It also has given me opportunities to attend national education and leadership conferences. I am now a member of Maine Insurance Agents Association board and serve as Vice Chairwoman. I really enjoy being involved in the association for our industry at the state level. I am also on the board for the local YMCA, I serve as Secretary on the Executive Committee.

What was your first job? Raking blueberries – not only was I terrible at it (very slow), it was the hardest physical thing I maybe had ever done at that age, and I didn’t last past the first day. Growing up in Maine, you see people rake blueberries and you can start doing that fairly young, so I was so excited once I was old enough to do it, and then it was so hot and terrible. After that I scooped ice cream and waitressed many summers in Bar Harbor. There is no better training for customer service and generally learning how to deal with customers and fellow co-workers than working in a restaurant, especially a busy restaurant in a tourist town.

What do you like to do outside of the office? Outside of the office I like to spend time with family and friends doing things outside. Downhill skiing in the winter, golfing and boating in the Summer. We live on a lake and I grew up on Mount Desert Island, so spending a day swimming and boating on the lake or the ocean during the summer is the best.

How do you create and maintain a work/life balance? Whenever possible it is great to participate in fun insurance/ community/ work events where you can relax and have fun with it still being a benefit to your career and business. Also, I try to do my best to recognize and prevent burnout whenever possible. Being rested and happy will make you better at your job and more present in your personal life. There is no sense in running yourself ragged and in turn not doing either one well. 


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