STRATFORD – Newly elected Democratic Mayor David Chess has added three key people to vital positions.
Joining Chess’ team are Caryn Kaufman, chief of staff; Thomas Tesoro, human resources director; and Caitlin Bosse, acting finance director.
“My administration is committed to taking a fresh look at how Stratford delivers services and results for its residents and business community,” said Chess. “We have opportunities to modernize how government serves the people and how we make the most of new technologies and approaches to how we do business. I’m building a team that can help move Stratford into the 21st Century.”
Kaufman brings more than three decades of experience in strategic communications, public affairs, and reputation management across the public, private, and nonprofit sectors. She recently returned to Connecticut after serving as chief communications officer for Ascension Wisconsin, part of a $28B national nonprofit health system. In addition to launching her own marketing and communications consultancy, she also previously served as the City of Bridgeport’s communications director during the Fabrizi administration.
Tesoro, J.D., has more than 30 years of global experience in HR strategic planning across several industries, he has an established record of success in HR strategic planning. He has led union and non-union employee relations, aligned human capital to strategic plans, and spearheaded organizational training and development programs. He is an adjunct professor of business law and employment law and has taught graduate courses on change and innovation.
Bosse, MBA, who joined Stratford’s finance team earlier this year, served 18 years as Fairfield’s Controller, where she was responsible for a $380 million operating budget, $400 million in capital projects, and $45 million in town investments. Bosse is skilled at streamlining processes, increasing reporting transparency, and optimizing municipal investments.
Chess defeated Republican incumbent Laura Hoydick in the November general election in 2025.
