MAYOR DAVID CHESS
FOR IMMEDIATE RELEASE
Media Contact: Caryn Kaufman, mayor@townofstratford.com, 203-385-4001
Chess Administration Kicks Off New Year with New Leaders
January 5, 2026 – Stratford, Conn. – Stratford Mayor David Chess welcomes several new leaders to his administration. Joining his 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,” stated 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.”
New Leaders
Caryn Kaufman has joined the Chess administration as Chief of Staff. She brings more than three decades of experience in strategic communications, public affairs, and reputation management across the public, private, and nonprofit sectors. Kaufman recently returned to Connecticut after serving as Chief Communications Officer for Ascension Wisconsin, part of a $28B national nonprofit health system, where she led enterprise, change management, and COVID-19 communications. 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.
Thomas Tesoro, J.D., will lead the Human Resources (HR) department for Stratford. With over 30 years of global experience across diverse industries, he has an established record of success in HR strategic planning, organizational re-engineering, and change management. Tesoro 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.
Caitlin Bosse, MBA, who joined Stratford’s finance team earlier this year, has accepted the acting Finance Director position. She previously served 18 years as Fairfield’s Controller, where she was responsible for a $380M operating budget, $400M in capital projects, and $45M in town investments. Bosse is skilled at streamlining processes, increasing reporting transparency, and optimizing municipal investments.
Additional staffing announcements will be made in the coming weeks. To view open positions, including chief administrative officer, town clerk, and director of communications and constituent services, please visit the Town of Stratford website.
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