Leading Insurance Agency in Massachusetts Celebrates 60 Years

Connie is a licensed broker for all lines of insurance and has been in the industry for 38 years, 20 of them with C&S! She has been married for 40 years and has two adult daughters.

This month, C&S Insurance celebrated its sixtieth anniversary as a leading insurance agency in Massachusetts. Sixty years of delivering the best in home, auto, and business insurance: definitely a milestone! In true C&S fashion, we threw a party to mark the occasion…

Held at TPC Boston, our 60th Anniversary gala gave us an opportunity to bring together all the amazing folks who’ve helped us build, prosper, and grow. We were delighted to share the evening with our incredible employees (some who have been with us since the first generation), along with many of C&S’ long-time clients, as well as our friends from partnering insurance companies.

Hard to believe it was actually sixty years ago, in October 1959, when B. Benjamin Cavallo and Frank Signoriello opened their doors to Mansfield families and businesses. Outwardly, things were very different then, of course. But the main tenets of our agency and its guiding philosophy remain the same.

After dinner, C&S’ current principals, Keith Signoriello and Ben Cavallo, shared a bit about the history of the company—outlining their fathers’ parallel paths and shared goals, six decades ago. For those who didn’t already know, Ben and Frank grew up on the same street in Mansfield. They were both Italian immigrants, whose families stressed the value of hard work and education. They both served their countries, and went on to earn college degrees from Bentley.

Both men went into accounting. For years they used to commute into Boston, on the train, to their respective CPA firms. At one point, Frank was auditing an insurance agency in Braintree; he thought it sounded like an interesting model. From there, C&S Insurance was set in motion.

“Ben & Frank were true entrepreneurs,” explained Keith Signoriello. “Our fathers never shied away from opportunity; they weren’t afraid to try their hand at a new endeavor.” To this point, and in addition to the insurance company, C&S’ founders ran a real estate company, an accounting business, an oil company, a development company, a liquor store, and a hotel.

Ben Cavallo went on to highlight the direction of C&S over the past 20 years, with second-generation perspective at the helm. The two current owners winnowed the agency’s focus, grew the company ten-fold in size—via a series of acquisitions—and built out a game-changing commercial lines department, putting C&S on the short list of top agencies for Massachusetts business insurance.

On behalf of Ben and Keith and the rest of the C&S team, we want to extend a huge thank-you to everyone who came out and celebrated with us. It’s a credit to everyone in the room on Thursday night (not to mention the thousands of valued clients who could never fit in one room) that C&S is now a leading insurance agency in Massachusetts. Your involvement, loyalty, and trust have allowed us to build on Ben and Frank’s original vision. With all of you in our corner, we’re excited to see how much better we can be at the 75-year mark!

A giant thank-you is also owed to the crew at TPC Boston, Judy’s Village Flowers, Brookline Ice Co., and the inimitable Steven Higgs. See you all in 2034!