Our History

Dolan Insurance Agency was founded in 1983 by Joe Dolan. Joe entered the insurance industry after leaving the Navy in the 1940's. Prior to founding Dolan Insurance Agency he worked for numerous insurance companies and insurance agencies in the Boston area. In 1983 he started Dolan Insurance Agency on the dining room table of his family's home in Milton, Massachusetts. Within a year or so, Joe purchased a small insurance agency in Framingham, Massachusetts. 

In 1985 Joe’s son, Tom Dolan, Sr., joined the family business. Prior to 1985 Tom had worked for a few insurance companies in Vermont. Joe and Tom decided to move the agency to Westborough, Massachusetts in mid-1985. That same year, Tom’s wife, Maura, joined the agency and quickly became “the real boss.” They set up shop in Tom and Maura’s living room, and eagerly solicited friends, family, in-laws and out-laws. In a few short years, Dolan Insurance Agency nearly tripled in size.

In 1986 the growing agency moved a few blocks away to 18 Lyman Street. A local business run by the extended Colangelo family (owners of the Westborough Shopping Center) took Tom, Joe and Maura under their wings. The Colangelo's introduced the Dolan's to the blossoming Westborough community. Within a few years, Phil Mulcahy joined the team and quickly became one of the agency's most valuable staff members.

In 1995 Paul Maloney, Sr. joined the agency. Paul grew up in Newton, Massachusetts. After graduating from Boston College, he held a variety of executive roles for insurance companies in Connecticut. When word spread that Paul was thinking of moving his young family back to Massachusetts, Tom suggested that they become business partners. Shortly thereafter, Dolan Insurance Agency became Dolan & Maloney Insurance Agency. 

In 2001 the agency moved from 18 Lyman Street into a small building located on Route 9. The new location provided improved visibility and met the need for additional office space. The late 2000's brought even more family to the organization when Patrick Tobiasson, PJ Maloney, and Tom Dolan, Jr. joined the team. 

Our business had humble beginnings on a dining room table. We owe many thanks to the ongoing support of our industry partners, our staff, our family, our friends, and our loyal customers. We could not have done it without you.