Third-Generation Independent Agent and Current Salem Five Insurance President to Retire January 2, 2025
By Joe Bartolotta
His family had been in insurance for nearly five decades, but when Brian Boyle graduated from St. Michael’s College in 1983, he wasn’t sure if he was going to join the family’s business with his father and brother.
After talking it over with his father, the younger Boyle decided to give it a shot – if for no other reason that he didn’t have another job lined up. That’s when his father doled out the reality: “If you’re going to work for me,” Brian recalled his father telling him, “You’re not going to be one of those kids who travel to Europe for the summer. You start June 1.”
Forty-one years and no regrets later, Brian Boyle will retire January 2, 2025, as president of Salem Five Insurance, the successor organization to Boyle Insurance.
“I’ve loved every minute of it,” Brian said recently. “I enjoy the people. The people in the agency and the underwriters we work with. The people in the Bank. And, of course, the people we insure. I may not have been certain about my career when I was leaving St. Mike’s, but I definitely made the right choice.”
Salem Five Insurance traces its roots to 1935, when Edward G. Boyle, an attorney in Woburn, helped new homeowners get insurance policies. It remained a side business for the Boyle family until Edward’s son, Gerard F. “Spike” Boyle, took over and focused on personal lines, but also sold real estate.
“To grow the business, he realized he had to focus on real estate or insurance. He chose insurance,” Brian said. “It was obviously a very smart move.”
Eventually, Brian and his older brother, Gerard F. “Jay” Boyle, Jr., began working in the insurance agency. Jay Boyle began in 1978 and, within a few years, expanded the agency’s products to include commercial lines. Brian joined in 1983. Meanwhile, Jay took over as president in 2000 when his father retired and retained the title until his retirement in 2022.
“Under Jay and Brian, Boyle Insurance really came into its own as a full-service insurance agency,” said Bruce Potter, Chief Operating Officer at Salem Five. “When we began looking at adding an insurance agency in the early 2000s, we quickly realized these were the right guys and the right team to join Salem Five. They knew how to balance the needs of the business with the needs of their customers.”
Boyle Insurance had $24 million in premium when it was bought by Salem Five in 2006. Today, it has more than $140 million. The acquisition by Salem Five completed the Bank’s commitment to providing customers with a full range of financial services, along with banking, mortgage, and wealth management services.
“After the merger, Jay and I figured we’d stick around for three years or so,” Brian recalled recently. “But the team here at Salem Five was just so great to work with that we decided to stay.”
In doing so, Brian, Jay, and the management team at Salem Five oversaw some of the largest changes in the insurance agency business, including the 2008 regulatory change that introduced competition to the Massachusetts auto insurance business. “Brian will be missed, he has a profound understanding of the insurance business, considered to be a visionary and thoughtful leader, a true professional,” Potter stated.
With retirement approaching, Brian plans to spend time with his wife, children and grandchildren, in addition to skiing and playing golf.
“I’m a very fortunate guy,” Brian said. “I got to work for my dad and my brother for 23 years. I’ve worked for 18 years now with the team at Salem Five. If I did it all over again, I’d do it exactly the same.”
