For the 2025 Wilton Municipal Elections, GOOD Morning Wilton asked all candidates to submit a 150-word bio; candidates running for the Boards of Selectmen, Finance and Education and the Planning and Zoning Commission were asked to sit for a video interview and submit an 800-word op-ed. In addition, candidates in the other races were invited to submit an op-ed if they wanted. More information is available in GMW’s Election Guidelines and Policies.

GMW Video Interview

Candidate Submitted Bio

Matt Raimondi, a Wilton native, is proud to serve the community as Chair of the Board of Finance. Elected in 2021 and unanimously chosen as chair in 2023, he has prioritized transparency, fiscal responsibility and long-term planning. Under his leadership, the board has modernized the budget process, introduced newsletters and surveys to better engage residents, and emphasized a collaborative, analytically rigorous approach to budgeting — balancing investments in schools, infrastructure and community needs with taxpayer priorities.

Professionally, Matt is the Managing Partner and CIO of Stonelight Capital Partners, a private investment firm, where he applies fiscal discipline and strategic thinking to guide businesses through growth and change. For Matt, Wilton is more than a hometown: it is the community that shaped him, and one he is committed to serving with steady leadership and a clear focus on the future.

Candidate Submitted Op-Ed

From Wilton, For Wilton: Leading with Transparency and Long-Term Vision

by Matt Raimondi, Republican Candidate for Board of Finance

Wilton isn’t just where I grew up; it’s where I learned the value of community. I went through our schools, built lifelong friendships here, and now have the privilege of serving as Chair of the Board of Finance. Over the years, the town has evolved, but one thing hasn’t changed: the spirit of community that makes Wilton special.

That spirit is why I serve — to give back to the community that raised me and to keep Wilton strong for the next generation. Public service is about stewardship: being honest about challenges, making disciplined choices and planning for the future. As costs rise and budget pressures mount, Wilton needs leadership that can balance today’s needs with tomorrow’s realities. I’m running for re-election because I believe in steady leadership built on transparency, accountability and long-term vision.

A commitment to transparency and accountability has guided my work on the Board of Finance since I was elected. Staying connected with residents has been a key part of that effort: I meet regularly with community groups, led the board’s town-wide survey to gather input, and launched the BOF newsletter to share clear, straightforward updates. Transparency isn’t just publishing numbers; it’s about building trust and helping people understand how and why decisions are made.

I also take pride in bringing discipline to the details. Since I joined the board, I’ve led its financial analysis through each budget cycle. In last year’s budget review, I went through hundreds of pages line by line to ensure accuracy, identifying roughly $1.4 million in discrepancies that, once corrected, reduced the levy for Wilton taxpayers. That is what public service should look like: doing the homework, asking tough questions, and making sure every dollar is accounted for.

I’ve guided the Board to start the budget process earlier and establish a clearer long-term plan. Engaging sooner has allowed us to work more closely and collaboratively with the Boards of Selectmen and Education, ensuring budgets reflect shared priorities and real constraints. Those conversations aren’t always easy, but they’ve strengthened mutual understanding and built a healthier working relationship among the boards. 

Additionally, under my leadership, the board adopted long-term forecasting tools that give both town officials and residents a clearer view of how today’s choices affect tomorrow’s costs. I also led the creation of long-term funding mechanisms, such as the Capital and Non-Recurring Expenditures Fund, to ensure future capital projects are planned responsibly and without creating undue financial strain for taxpayers.

Fiscal discipline is about balance. Wilton must invest in its schools, infrastructure and essential services, but we must do so responsibly. The board’s job is to protect the quality of life that makes this town exceptional while keeping it affordable for families and competitive for the future.

I’m running for re-election to continue strengthening Wilton’s financial foundation and protecting what makes this town special. The next few years will bring important choices about how we grow and invest in our future, and my objective is to ensure they are made with discipline, transparency and collaboration. Wilton’s success depends on constructive partnership among its boards, and I’m proud of the progress we’ve made working together toward shared goals. My commitment is simple: to keep leading with steadiness, accountability and a focus on Wilton’s long-term success.

I’d be honored to continue this work and earn your vote for another term on the Board of Finance.

Candidate Interview Clips

Q: Tell people why you deserve to be elected to the Board of Finance.

Q: Going forward, what’s your sense of how Wilton will move ahead given its current financial state?

Q: Is there concern that the recent issues in town could impact Wilton’s finances or its bond rating?

Q: The Process Review Committee was supposed to choose an outside investigator — is that still happening?

Q: You’ve been very visible at Board of Selectmen meetings — is that typical for a Finance chair?

Q: With so much overlap in responsibilities, would your efforts be better spent running for the Board of Selectmen?

Q: You came up with the idea of a “quad board survey.” Why is it important, and what’s its goal?

Q: How are voters’ attitudes this election cycle compared to four years ago? What are voters telling you specifically about Board of Finance issues — taxes, budgets, Town Hall?

Q: What would you like to see the Board of Finance do differently or better as a body?

Q: Some say the $150 million capital projects figure is exaggerated — what’s your take?

Q: Is the Board of Finance hard enough on the Board of Education when it comes to spending increases?

Q: Some say Wilton has “penny-pinched” too much — should the town invest more in infrastructure and amenities?

Q: Given recent turmoil, does Wilton need major changes like a charter revision or staffing restructure?

Q: Should the Board of Finance have its own legal counsel, separate from the town attorney?

Q: Last year’s town budget process was difficult — what will you do differently this year?

Q: How much purview does the Board of Finance have over the CFO and the Finance Department?

Q: What are your thoughts on the proposed tax sale — is it a good idea?

Q: How important is your reelection in light of the current “crisis” in Town Hall?

Q: Have you ever considered running for First Selectman?

Q: Can you address criticism over how the Board of Finance handled the Ambler Farm lease?

Q: What’s your stance on selling off town properties to raise revenue?

Q: Give us your 30-second elevator pitch — why should voters elect you to the Board of Finance?