Our Indispensable Team

    Our team spans three generations of the DiMatteo family, providing deep experience and continuity to our clients as they work toward their version of success.

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    Our Team


    John DiMatteo, CFP®, CPFA

    CEO | Financial Advisor


    John Esposito, AIF®

    Financial Advisor


    Dave Attolino, CPFA

    Client Service Associate


    Jessica DiMatteo

    Financial Assistant


    John DiMatteo, CFP®, CPFA

    CEO | Financial Advisor

    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 with 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 whom I remain close with to this day. I earned a bachelor's degree in chemical engineering because at the time I liked math and science. When you're young, it is difficult 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 parents, Lena and Tony DiMatteo'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. We serve thousands of families in the Fairfield and New Haven county areas, providing all types of property/casualty, life/health insurance, tax and accounting services, and comprehensive financial planning services.

    In 1996, I obtained my CERTIFIED FINANCIAL PlANNER professional certification, and I’ve focused on the financial planning side of the business ever since. 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 nephew and godson, Johnny Esposito, who represents the third generation of the family, joining the firm in 2017; and Diane Lemanski, my wonderful financial assistant who has more than 30 years of experience. 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 more than $412,000 for various local charities, including the Kennedy Center, Boys and Girls Club of the Lower Naugatuck Valley, Spooner House, BH Cares, and many other worthy causes over the years.

    I’m lucky to be married to 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 for a large national insurance company; our middle daughter, Jessica, attends the University of Connecticut; and our youngest son, Michael, attends the University of Tampa.

    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.


    John Esposito, AIF®

    Financial Advisor

    I am originally from Shelton, Connecticut, and have lived there all my life until recently moving to Middlebury, Connecticut, with my beautiful wife, Amanda, and son, Luca. I grew up in a close-knit Italian family on both sides, the Espositos and DiMatteos. I attended Shelton High School, where I played soccer and became a part of the founding lacrosse team in 2004.

    In 2008, I was accepted into Western New England University on a lacrosse scholarship but ultimately decided to join and help found WENU’s rugby program. We won the NERFU D4 championship the first year as a team. I still support the rugby team to this day by donating and playing the annual WNEU Rugby Alumni game. I earned a bachelor’s degree in finance in 2012.

    During summers while in school, I did everything from servicing pools, installing cubicles, interning at Sikorsky, and traveling the country organizing 3v3 soccer tournaments for kids. In my junior year of college, I met and started dating my future wife, Amanda.

    One of the highlights of my college career was getting the opportunity to study abroad in Florence, Italy. There, I was able to visit my family roots in Calabria, Abruzzo, and Naples and had the opportunity to meet some of my cousins and visit with an aunt and uncle, whom I hadn’t seen since I was a toddler.

    After graduating from college, it was tough finding a job as the economy and job market were still recovering from the great recession of 2008. During that time, I went back to working on pools and cleaning windows. Eventually, I found a job in Boston developing business for a corporate payment and foreign exchange trading solutions company. After a short while there, I received a call to interview at GE Capital in Norwalk, Connecticut. It was a great opportunity. I took the interview and landed the job as a portfolio analyst in commercial lending operations. Two years later, the news hit that GE was selling off the lending business and our jobs would be terminated.

    I thought this would be a great time and opportunity to follow in the family footsteps and join the business that my grandparents built. So here I am today, enjoying coming into the office; seeing my mother, two aunts, and two uncles; and being able to work with them on a professional level to help grow the business and pass on the legacy of my grandfather and grandmother to a third generation.

    I truly enjoy what I do now! I love helping people of all ages prepare for and navigate through retirement. I also love helping small businesses take their practice to the next level in setting up retirement plans and training their employees on the benefits and investments within the plan.

    My time is mostly taken by my young family and continuous home improvement projects. However, in my spare time, I enjoy hunting and fishing, woodworking, and mixed martial arts.


    Dave Attolino, CPFA

    Client Service Associate

    I was born and raised in Orange, Connecticut, in a close-knit family and currently reside in Hartford, Connecticut. I attended Amity High School, where I played football and was also heavily involved in coaching the Special Olympics, primarily in track and field and floor hockey.

    After I graduated high school, I decided to attend Ithaca College to continue my football career. I thoroughly enjoyed my time at Ithaca College. In my time at Ithaca, our football team won the Empire 8 Conference championship and made it to the quarterfinals of the Division-3 College Football Playoff. As a student-athlete at Ithaca, I strived to soar on and off the field and maintain a strong performance in the classroom. After my freshman year, I made the decision to transfer to the University of Connecticut because of the high costs of attending a private college and a desire to be closer to my friends and family.

    At UConn, I declared as an economics major because of my interest in microeconomic principles, specifically understanding consumer decision-making and resource allocation. I loved every second of my time at UConn. I had an on-campus job as a bus driver, I worked as a volunteer with the Big Friends mentorship program, and I coached a Special Olympics bocce team.

    During the summers, I kept myself busy working as a general laborer for my uncles, who were residential contractors, and outside operations over at Great River Golf Club. A common misconception about me is that because I worked at a golf course for eight years of my life, I should be a decent golfer; however, my scorecard often resembles a bowling score.

    Once I graduated, I was hired working sales and account management for a medical supply and equipment distributor. I worked in this role for almost two years and then accepted a new role with a staffing and recruiting agency. I eventually left that position for my current role as a client service associate.

    The opportunity to work for a family-owned business is one I am grateful for, especially the DiMatteos. I have had a long-standing relationship with their family, having grown up close with John’s oldest son, Anthony. They have welcomed me into their home countless times and now have welcomed me into their family once again. The Dimatteo Group’s guiding principle is putting the needs of others before your own, and it is the philosophy that aligns perfectly with the values my family has instilled in me.

    I enjoy my role of getting to work with both businesses and their employees. Retirement plans can be a tricky thing for all stakeholders: from the business owner’s perspective, offering a plan that is cost-effective and ensuring compliance with the numerous IRS, DOL, ERISA rules and regulations, and for the employees, figuring out a retirement strategy that fits their goals and risk level. Helping business owners and their employees tackle these dilemmas is what I enjoy most about this job.

    In my spare time, I enjoy playing pickup basketball, attempting to golf, and attending UConn sporting events. I have a lifelong goal to attend a Super Bowl, NBA finals game, and World Series game. I root for the New York Knicks and Mets, as well as the Los Angeles Chargers.

    I am a Certified Plan Fiduciary Advisor (CPFA). This designation recognizes financial professionals who demonstrate expertise and experience working with retirement plans.


    Jessica DiMatteo

    Financial Assistant

    I grew up in Bethany, Connecticut, with many relatives and friends living close by. In addition to this, belonging to an Italian household has taught me the simple delight of enjoying Sunday sauce while hosting good company. I attended Amity Regional High School, and I was blessed to have spent my after-school hours learning and working alongside my grandmother at her small horse farm. Luckily, after a lifetime of mucking stalls, I can finally be endorsed on LinkedIn for this skill!

    I joined DiMatteo Group as a part-time employee in August 2020, after graduating magna cum laude from the University of Connecticut with a BS in sustainable plant and soil systems. I was a frequent DiMatteo Group intern during my time at UConn, and I was also fortunate to live with a host family while studying the Spanish language, literature, and culture for a semester at the Universidad de Granada in Spain. ¡Tenéis que probar las tapas!

    Pre-pandemic, I began a new chapter in academia, assisting with running a pre-clinical behavioral neuroscience laboratory. Post-pandemic, as someone with the need for constant engagement, I knew that the time was right to continue learning about the family business. I worked my way into the position of Financial Assistant in January 2021, and I now enjoy meeting with and learning about our clients to help them achieve their financial goals. In the fall of 2021, I will pursue an MBA at the University of Tampa.

    I own a Quarter Horse named Ray, and we enjoy trail rides, as well as western pleasure and hunt seat disciplines. When I’m not in the office or at the farm, I often remain active through my weekly Murph workout. Consider yourself lucky if you don’t know what that is! Above all, I appreciate spending time with my family.