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.
Jessica DiMatteo, MBA
Matthew Schock, CPFA
Plan Education Specialist
John DiMatteo, CFP®, CPFA
CEO | Financial Engineer
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 nephew and godson, Johnny Esposito, who represents the third generation joining the firm in 2017, as well as my daughter, Jessica DiMatteo, who joined the firm in 2020. 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 $442,000 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 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 the vice president of operations for an insurance agency in Tampa; our middle daughter, Jessica, graduated from the University of Connecticut and attends graduate school at the University of Tampa; and our youngest son, Michael, graduated from the University of Tampa and works as a regional account manager for a large cybersecurity company.
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®
I am originally from Shelton, Connecticut, and have lived there all my life until 2017. I currently reside in Middlebury with my beautiful wife, Amanda, two sons, Luca and Lorenzo, and Standard Goldendoodle, Buddy. 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 WNEU’s Rugby Program. We won the NERFU D4 championship the first year as a team. I still support the rugby team to this day, donating and playing the annual WNEU Rugby Alumni game. I received a bachelor’s degree in finance from WNEU in 2012.
During the summers, 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 meet some of my cousins and visit my aunt and uncle, whom I haven’t seen since I was a toddler.
After graduating college, it was tough finding a job as the economy and job market were still recovering from the great recession of 2008. In the meantime, I went back to working on pools and cleaning windows and eventually found a job in Boston developing business for a corporate payment and foreign exchange trading solutions company based out of Canada. After a short while there, I received a call to interview at GE Capital in Norwalk, Connecticut. Being such a great opportunity, I took the interview and landed the job as a portfolio analyst in commercial lending operations. Two years passed and 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's 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, helping people just like myself, sometimes older, sometimes younger, prepare for and navigate through retirement. I also love helping small businesses take their practice to the next level in setting up retirement plans, finding the best fit for them, and training their employees on the benefits and investments within the plan.
My spare time is mostly taken by my young family and continuous home improvement projects. However, in the spare time I do have, I enjoy hunting and fishing, woodworking, and mixed martial arts.
Dave Attolino, CPFA
Retirement Plan Specialist
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 the 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 to work as a sales and account manager 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, and 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, MBA
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 consider myself immensely fortunate and appreciative of the opportunity to collaborate with both of my parents in this dynamic industry. Working alongside them, I am dedicated to delivering exceptional service to our cherished investors.
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, studying, cooking, 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 friends and family.
Matthew Schock, CPFA
Plan Education Specialist
I have grown up and lived in Cheshire, Connecticut, all my life. I lived with my mom and brother at home and have more family in Connecticut and Massachusetts. Since everyone is so close, I can 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 and feel more secure about your retirement 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 just a puppy, so she has a lot of energy to keep 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.
We’re ready to start planning your future whenever you are. Reach out to our team to begin.