Our Leadership Team

I grew up in Stratford, Connecticut, in a close family with almost all my relatives living nearby. We enjoyed Italian feasts on a weekly basis with all of them, and it was so special having my grandparents with us. I attended Bunnell High School and played football, basketball, and baseball as a kid, including the Stratford Eagles National Championship team of the early ’70s. (We tied 0-0.)

At the University of Connecticut, I joined Sigma Phi Epsilon Fraternity and met many great friends that I remain close with to this day. I studied and received a bachelor’s degree in chemical engineering because at the time I liked math and science. Being young, it is so hard to know exactly what and where you want to be.

I moved to Houston, Texas, shortly after graduating and made my first bad investment in Houston real estate. I worked in the oil production service field (mud engineer) for two years, and then sold Teflon-lined valves to the chemical industry for three years, and enjoyed traveling the country.

Family values stay with you for life. The opportunity arose to join my mother and father’s property/casualty insurance business, and I soon decided I liked working with and helping people much more than math and science. The decision was timely because I moved back to Connecticut and met my beautiful wife, Kim, shortly thereafter. Kim also joined the firm, along with my three sisters and brother-in-law. Our parents taught us early the virtues of hard work and always putting our clients’ needs first, as well as the importance of giving back to the community we serve. I believe this is why we successfully grew the firm from a small 500-square-foot office to a thriving 5,500-square-foot building in Shelton with close to 30 employees before its sale to Cross Insurance in 2019.

In 1993, I obtained my CERTIFIED FINANCIAL PLANNER™ professional designation, and I’ve focused on the financial planning side of the business ever since. We serve thousands of families in the Fairfield and New Haven County areas, providing all types of life insurance, tax and accounting services, and comprehensive financial planning services.

I really feel my strength in mathematics and science has been a benefit to our clients, especially my attention to detail. I take great pride in working with my daughter, Jessica DiMatteo, who joined the firm in 2020, and my son, Michael DiMatteo, who joined the firm in 2025. Having the next generation learning the business now ensures we will be here to help your next generation, too.

In 2005, we created the DiMatteo Family Charitable Foundation in honor of Tony as he successfully battled colon cancer. To date, we have raised over $636,000 for nearly 20 charities in the past 18 years, including local and national nonprofits such as Adam’s House, The Boys & Girls Club, and the Kennedy Center.

I’m lucky to be married to my wife, Kim, and we have three fantastic children (yes, that’s a proud father talking!). Our oldest son, Anthony, graduated from the University of Connecticut and works as a P&C Consultant for an insurance agency in Connecticut; our middle daughter, Jessica, graduated from the University of Connecticut and received her MBA from the University of Tampa, and works at DiMatteo Group Financial Services as a financial advisor; and our youngest son, Michael, graduated from the University of Tampa and now works here with us at DiMatteo Group Financial Services as our Sales Coordinator.

Our family enjoys traveling, especially to Redington Shores, Florida, and Florence, Italy. We are active and exercise regularly, especially racquetball and horseback riding. Kim grew up riding on her mom’s horse farm in Bethany and her passion for horses has rubbed off on Jessica over the years. We now have a horse stable at our home and enjoy riding on the trails of Bethany regularly.

I grew up in Bethany, Connecticut, surrounded by many relatives and friends living close by. Being raised in a large Italian household taught me the simple joy of sharing good company over Sunday sauce—a tradition I still treasure today. I attended Amity Regional High School and was fortunate to spend my after‑school hours learning and working alongside my grandmother at her small horse farm. After a lifetime of mucking stalls, I can finally say it’s a skill worthy of a LinkedIn endorsement.

I joined DiMatteo Group as a part‑time employee in August 2020, after graduating magna cum laude from the University of Connecticut with a Bachelor of Science in Sustainable Plant and Soil Systems. During my time at UConn, I was a frequent DiMatteo Group intern and had the opportunity to study Spanish language, literature, and culture for a semester at the Universidad de Granada in Spain. ¡Tenéis que probar las tapas!

In 2023, I earned my MBA from the University of Tampa, marking an important milestone in my professional journey. Shortly thereafter, I returned to DiMatteo Group full‑time and was promoted to Financial Advisor at the beginning of 2025. Soon after, I advanced into the role of Director of Financial Planning, where I play a key part in developing comprehensive, client‑focused strategies.

I consider myself incredibly fortunate to work alongside my family in this dynamic industry. Today, I collaborate closely with both of my parents and my brother, Michael, and together we are committed to delivering thoughtful, fiduciary‑focused advice and exceptional service to the investors we are proud to serve.

In January 2026, I married my husband and best friend, Steven LaChance, and we enjoy building a life grounded in family, shared values, and plenty of time outdoors.

Outside of the office, I own a Quarter Horse named Ray, and we enjoy trail riding as well as western pleasure and hunt seat disciplines. When I’m not working, studying, cooking, or at the farm, I stay active with a weekly Murph workout—consider yourself lucky if you don’t know what that is. Above all, I value spending quality time with my family and friends.

I now live in Naugatuck, Connecticut, but had grown up and lived in Cheshire, Connecticut, all my life. Growing up, I lived with my mom and brother, both of whom still live in Connecticut. Since everyone is so close, I am lucky enough to see them often. I attended Cheshire High School, where I participated on the swim team for all four years and was a captain for two years. My main event was the freestyle, and I greatly preferred sprinting events over distance ones.

After high school, I chose to attend the University of New Haven, majoring in criminal justice with a concentration in law enforcement. Apart from working hard on my grades, I also worked with others to create a club swim team on campus. While we did not compete much during my time on the team, it was nice to be able to continue swimming. This also allowed me to work as one of the team lifeguards.

After changing my concentration to investigative services, I took an internship as a probation officer. This job made me realize the importance of working somewhere where I could help people. After graduating, I was unsure of what I wanted to do, and due to the pandemic when I graduated in 2020, things were constantly up in the air. My first job out of college was working with life and health insurance, focusing on Medicare. This was another good opportunity to help people by teaching them to navigate that system and reduce their confusion about the process.

I ended up leaving that position and was lucky enough to come across the opportunity to work here at DiMatteo Group. Working at a family-owned business has been an incredible experience. What I enjoy most about my role is the ability to help people. Retirement planning can be confusing and stressful when trying to tackle it independently. There are many rules to follow when it comes to your plan, and those rules are constantly changing. Being there to help you navigate these obstacles is the most important aspect of my work.

In my free time, I enjoy playing with my golden retriever Elsa, hiking, and maintaining/upgrading my aquarium at home. I have always loved dogs, and Elsa is my second golden retriever. She is still has the energy of a puppy, which certainly keeps me busy. Living in Connecticut for so long has also given me an excellent opportunity to try out many of the different hiking trails in the state, with the main place I hike being Sleeping Giant in Hamden.

I’m proud to be a Connecticut native, born and raised in the small town of Bethany. Growing up in a big Italian family, I learned early on the importance of hard work, meaningful relationships, and truly appreciating life’s moments. Those roots continue to shape who I am—someone who values connection, loyalty, and showing up fully in both personal and professional settings.

My career path has taken me from studying Entrepreneurship at the University of Tampa to leading high-performing sales teams in the tech sector, and now, to working alongside my family at DiMatteo Group Financial Services. At every step, I’ve been driven by a desire to help others—whether that’s closing a key deal, solving a complex problem, or supporting the team as they guide clients toward financial clarity.

I began my professional journey in software sales at Seamless.AI, where I was promoted from Sales Development Representative to Account Executive in just three months. I then joined KnowBe4, a global cybersecurity leader, where I became a top producer in my division and earned Presidents Club honors. These roles taught me the value of perseverance, preparation, and a client-first mindset.

Today, I bring that same dedication to our family firm, where I support the advisors in the area of retirement planning, and 401(k) strategies for businesses. For me, true success lies not just in financial outcomes, but in building lasting trust and creating meaningful impact.

Outside of work, I enjoy staying active, reading motivational and business books, and spending quality time with loved ones. Whether it’s Sunday family dinners or catching up with friends, those moments ground me and remind me of my purpose.

At the core of everything I do—professionally and personally—is a commitment to growth, service, and showing up for others. That’s what fuels my work every day at DiMatteo Group and beyond.

“2024 Presidents Club Award, presented by KnowBe4 a previous employer. Presented January 21, 2025, for the previous year’s sales production, and is not specific to financial services and does not imply an endorsement, recommendation or reflect the performance of the representative.”