Mary Boyd

CEO

Plymouth Rock Assurance 

Mary Boyd joined Plymouth Rock in 2018 and leads Plymouth Rock Assurance Corporation's independent agency business, including independent agency auto, Pilgrim services and umbrella liability. She has held multiple senior leadership positions, including heading The Hartford's personal lines agency and personal lines direct channels and managing the company's AARP partnership. She also served as president of the Private Risk Services Division at ACE and was senior vice president and managing director at Explorer Insurance Company.

Boyd found her way into insurance first through her love of math and business, but secondly because of her aversion to becoming an accountant. The career that ensued has provided the full range of emotions. “It's been challenging. It's been rewarding. It's been exciting. It's been frustrating," she says.

How did you get started in insurance?

When I was in high school, I had a strong interest in math and a strong interest in business. When I was asked to do an assignment to identify what career I wanted, I went to the library in my high school and went to the “As." I knew I did not want to be an accountant—and then I stumbled upon actuary, which was described as someone who applied math to business problems and helped insurance companies set the price on products. It also said leaders in actuarial science often become the leaders of insurance companies. I thought, “Whoa, that sounds great." In college, I double majored in applied math and economics and took my first insurance job as an actuarial trainee at Chubb.

What are the challenges for women in insurance?

One of the strengths that many female leaders bring to the table is an organizational drive, attention to detail, multitasking capabilities and the ability to motivate teams in a multifaceted way, which is reported in research. In a business sense, that often lends advancement opportunities to be in operational or sometimes analytical roles. I've seen many instances across companies and agencies where the chief operating leader of the agency is female and the president is male, that while it's not intentional, that is oftentimes where it lands. There can be that second-fiddle kind of feel and that has been part of the glass ceiling. The ability to break through from that chief operating officer (COO) position to a CEO position can be very difficult. But, there is recently more progress and that is really exciting to see.

What's your favorite thing about working with independent insurance agencies?

Independent insurance agents are business owners that advance, build and represent their communities. There's no better way to bring the American dream to life than by being a business owner that supports the community and other businesses.

Independent agents are entrepreneurs. I work with folks that range from startups and from-scratch agencies to multi-generational businesses. Those multi-generational agencies aren't counting on their business to survive because they're big—they're always innovating and thinking of new ways to make their agency relevant, service their customers and make their employees happy, which is another thing. Independent agency owners think about their employees more than any other business. I really respect that because they understand that their business is successful because of their team.

What makes the insurance industry a great career choice for women?

It's a great career choice period. In the insurance industry, there is basically almost every kind of job that you could want to do. Also, as your lifestyle changes—from coming out of college to maybe starting a family, to becoming an empty nester—there are different opportunities that match up to that. A career in insurance resonates well for women because, oftentimes, we adapt our work to our family and lifestyle. That gives us the latitude to continue our professional pursuits and still show up for our family and our partners.

Best piece of advice you've ever received?

My dad used to say, “If you do your best, you'll always be a winner." That has stayed with me. He didn't necessarily mean I was going to win everything. He just meant that if I am doing my best, I'm a winner. It never made me feel good when I lost, but it always made me realize that losing was okay and that was part of getting better. You don't have to be the best. Just do your best.

If you could have lunch with any person who has ever existed, who would it be?

Eleanor Roosevelt. If there's someone in the world that could earn the respect of so many in terms of her role as a diplomat, an activist and a fearless supporter of human rights, but also a dedicated partner and wife, it's her. Although her husband was the chief citizen, I think she was the first citizen. She did everything right.

As a female leader, many of us become the second in charge. Whether it's in an insurance agency or an insurance carrier, we rise to a level that's very influential and is responsible for delivering and advancing the mission but may not have the most high-profile role. Eleanor Roosevelt embodied that in every way. I'd love to hear how she did it and how she felt about it. I'd also ask what her advice would be for folks today.

Will Jones is IA editor-in-chief.