DiMatteo Group Celebrates 50th Anniversary

Some families grow apart over the years but the DiMatteo family has grown closer together, especially since six relatives work side by side in the family business.

During its 50th anniversary celebration this year, the second generation has successfully led this Shelton-based company in new directions as they have changed their name from DiMatteo Insurance to DiMatteo Group to more accurately reflect all the services their business offers.

In 1960, the late Anthony DiMatteo of Shelton founded the insurance business with a partner in an office on East Main Street in Bridgeport. Little did he know how much this small business would expand and have such a big impact on the region as leaders in their profession and major community supporters.

The business thrived back then as it does today.  A few years after its opening, the insurance agency moved into a larger space on Huntington Turnpike in Bridgeport. By 1970, Anthony's wife Adeline "Lena" joined her husband and the company was renamed A.A. DiMatteo Insurance Service Center. (One "A" represents Anthony and the other "A" stands for Adeline.)

In 1993, the founders turned over daily business operations to their four children and two of their spouses.  Seven years ago the company acquired its current space on the Bridgeport Avenue corridor in Shelton. Since that time, the family business has managed to quadruple sales, triple its office space and increase staff to 20 highly trained professionals.

The business was recently renamed the DiMatteo Group to reflect its broad range of client services including:  insurance, employee benefits, income tax and financial services.

According to company President John DiMatteo of Bethany, the second eldest child and their only son, "We continue to maintain the integrity of our founders by offering personalized service and treating others as an extension of our family.  Each sibling or spouse manages a key department." 

"After 50 years, we restructured our business and all three divisions are united under the umbrella of the DiMatteo Group.  This new image offers our customers a big advantage because they can have a relationship with one company for all their insurance, financial, tax and accounting needs.  In the past, many of our customers did not realize everything we do."

Great customer relations are the backbone of the business.  According to Sandy Effren of Greyrock in Norwalk, "The DiMatteo Group is simply the best you can find in terms of insurance. You cannot beat their service and the agents are always on top of things. They cover all the bases and dot every 'I' and 'T.' As a customer for over 20 years, I have nothing but praise for the entire firm."

Tony Lucera of Contracting Advisors in Brookfield added, "The DiMatteo Group is a very customer service oriented business who is committed to taking care of all my insurance needs.  They take the time to make sure I receive the best price available."

"Great service and attention to detail are the hallmarks of success for the DiMatteo Group," noted John Ianiri of Fairfield County Millwork in Bethany.  "They are great people to work with both professionally and personally."

DiMatteo Group has received several merit awards over the years.  Most recently, the company was recognized for its 50th anniversary by the Greater Valley Chamber of Commerce at their quarterly Business Breakfast.  In addition, the agency received designation as one of a few exclusive agencies that offer the Home Builders' Program underwritten by The Hartford. The DiMatteo Group also has many competitive options for restaurants available.

All four siblings serve as officers of the company and have migrated into the business on their own.  John works with his wife, Kim DiMatteo, a partner in the business.  Loretta Lesko of Shelton, the second youngest sibling, serves as Vice President, while her husband Robert Lesko  is a partner. Likewise, Victoria DiMatteo of West Haven, the youngest sibling, holds the position of Secretary of the Corporation. It's all in the family with Rosemarie Esposito of Shelton, the eldest sibling, who is the agency's Treasurer.

The DiMatteo Group has always been a supportive corporate neighbor of the community.  This spirit of philanthropy resulted in the creation of the DiMatteo Family Charitable Foundation five years ago and their annual golf tournament. Their Foundation was established as a tribute to their father who was battling cancer at the time. 

"Our Family Foundation is committed to funding research, education and finding a cure for diseases that have touched the lives our friends, families, clients and staff," said John DiMatteo. "We are proud to have raised more than $100,000 for over 10 well-known local and national charities." Some of the charities they have supported included: St. Vincent's Swim Across the Sound, the American Heart Association and Juvenile Diabetes Association to name a few.

During the 50th anniversary, the DiMatteo Group will be allocating the proceeds from their 2010 and 2011 golf tournaments to a larger scale project for The Kennedy Center, one of the largest rehabilitation agencies in the state.  They will be working on group home renovations in Oxford, Monroe and Trumbull with supplies and manpower donated by their customers and staff, in addition to a $50,000 donation from the DiMatteo Family Foundation.

"We are thankful to all our friends, family members and customers who have so generously supported our golf tournament, which funds our Foundation," said John DiMatteo.  "We are honored to give back to the community for such a great cause as The Kennedy Center and to help people with disabilities live in a such a nurturing environment."

The late Anthony DiMatteo and his wife Lena never actively solicited any of their children to work with them. "One by one our four children gravitated back to the family business," said Lena.  "I am proud that my children earned the right to own this business through hard work. In high school, they helped us by doing extra chores around the house or filing papers in the office. I encouraged our children to first attend college and pursue their own interests. Their success is a testament to our family's values; they have succeeded well beyond our expectations. What more could parents want?"