by Kay Lee Ogden
This week’s Business Spotlight shines on Gilbert Insurance Agency, of Georgetown, managed by Daniel A. Stewart, and located in the Eagle Building, 37 West Main Street, Unit #2.
Dan and his lovely wife, Stephanie, are the proud parents of four wonderful young people. Their daughter Sarah, 28, is a maternity nurse at Portsmouth Hospital. Maddie, 24, owns her own business, Rise Up Fitness, where she works as a fitness and nutrition coach. Jack, 21, is an airplane pilot and attends SNU, while Patrick, 18, is a freshman at ASU.
Four terrific kids—and you can certainly hear the pride in their parents’ voices when they talk about them!
Dan’s own roots run deep in Georgetown. He grew up here and is the son of two of Georgetown favorites: Ruth Stewart and the late Dave Stewart. Ruth is now 90 years young, and she certainly isn’t slowing down! She continues to enjoy playing golf twice a week with her friends and grandchildren.
That connection to family and community has remained an important part of Dan’s life.

A Career That Wasn’t Planned
Dan’s entrance into the insurance business was not exactly part of some grand master plan.
He originally started out selling copy machines. Then, through his late mother-in-law, he was introduced to the insurance industry. Dan became intrigued by insurance and decided he wanted to learn everything he could. He worked for Gilbert Insurance in Reading, and through hard work and determination, progressively helped increase sales by millions of dollars.
Then, in March of 1996, Dan was awarded his own location in Georgetown from the main Gilbert Company in Reading, after being purchased from King Risk Partners.
And the rest, as they say, is history.
But Dan didn’t build the business by sitting behind a desk waiting for customers to walk through the door. He knocked on doors. He introduced himself to people and simply told them that if they ever needed help or insurance, they could give him a call. No hard sell.
No pressure.
Just a handshake, a conversation, and a willingness to help.
Dan believes that resilience and faith played an important role in his life, giving him the determination to believe in himself and keep going. His intelligence, dedication, and willingness to do his homework have also played a tremendous role in his success.
Today, Dan is a Certified Insurance Counselor (CIC) and an independent insurance professional.
And Dan has a philosophy that says a great deal about how he runs the business:
“I work for you—not the insurance companies.”
An Advocate for His Customers
Because Gilbert Insurance is independent, Dan can shop for insurance coverage and pricing among available insurance companies to help find options suited to his customers’ needs.
But to Dan, it goes far beyond simply finding a policy.
He believes that when a customer has a problem, he should be there to help fight for them.
Dan shared with me his concerns about what he calls a “hard market mentality,” particularly when customers experience significant claims. His philosophy is that his clients deserve an advocate who will stand beside them, communicate with the insurance company, and work toward a fair resolution.
That personal commitment is one of the reasons Dan has built the business through word of mouth, referrals, door knocking, and good old-fashioned hard work. People talk. Customers tell their friends. And relationships grow.
Insurance for Just About Every Need
Gilbert Insurance offers a wide variety of personal insurance, including homeowners, automobile, personal property, umbrella liability, boats, yachts, and valuable property coverage.
For businesses, the agency offers commercial property, commercial general liability, equipment and marine coverage, business automobile, workers’ compensation, commercial excess liability, Directors & Officers liability, Errors & Omissions liability, data breach liability, surety bonds, and fidelity bonds.
The agency also offers financial services, including term life insurance, universal life insurance, mortgage life insurance, disability insurance, annuities, IRAs, and more.
Dan believes there are often opportunities for people to save money while making sure they have the right protection.
That is why he is offering free insurance reviews.
His invitation is simple: Bring your policies in and let him take a look.
Dan will review your current coverage, shop for available options, and help you determine whether your policies provide the protection you need for your home, automobile, business, and other assets. If you decide to make a change, he can also help with the transition.
There is no charge for the review, and sometimes a second look can make a real difference.
Looking Out for the Community
Dan also has a strong message about driving safely.
He believes that cell phone use, alcohol, drugs, and other distractions are among the major factors contributing to accidents. Accidents and claims can have consequences that reach beyond the immediate situation, including their potential effect on insurance costs. His message is simple: Pay attention, drive responsibly, and protect yourself and everyone sharing the road.
Dan also points out that customers who donate to the Special Olympics may be eligible for savings on their automobile and homeowners insurance, depending on the applicable program and qualifications. Just another example of Dan knowing the “tricks of the trade” that may help his customers save money.
Behind Every Good Business is a Good Team
Dan and Stephanie are quick to express their appreciation for the people who help make Gilbert Insurance what it is today. Their dedicated employees include John Cronin, Commercial Customer Service Representative, and Colleen King and Fran Gesamondo, Customer Service Representatives.
And this appreciation is especially meaningful because when Dan faced some difficult health challenges several years ago, Stephanie stepped up to help care for Dan while also helping take care of the business.
Alongside her were the dedicated employees who continued taking care of their customers.
That kind of loyalty is something you don’t forget.
Thank You
Dan and Steph are also deeply appreciative of the customers and businesses who have trusted Gilbert Insurance over the years.
Among those Dan would like to recognize are Throne Depot of Billerica, Brakes and Clutch, G-Town Building Supply, Nunan’s Garden and Florists, and Trevor Stauble Services of Groveland, which specializes in heavy equipment repair and has been insured through Gilbert Insurance for many years. Dan would also like to give a special shout-out to Rebecca Fortacto, Branch Manager of Salem Five Bank in Georgetown, for her steadfast support throughout the years.
These are more than names on a customer list. They are relationships.They are friendships. And they are part of the story of a local business that has grown by taking care of people.
Built One Relationship at a Time
Gilbert Insurance Agency
Eagle Building, 37 West Main Street, Unit #2, Georgetown, MA
Phone: 781-942-2225, ext. 122
Fax: 781-942-2226
Email: dstewart@gilbertinsurance.com
Hours: 8:30 AM–5:30 PM
Nights and weekends by appointment
Dan’s invitation to you: Bring your current insurance policies in for a free review. Let Gilbert Insurance take a look—you may discover opportunities to save, improve your coverage, or simply gain peace of mind knowing you are properly protected.







