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Dr. Jennifer L. Zaccara is Vermont Academy’s eighteenth Head of School. She came to Vermont Academy in 2017 from The Nightingale-Bamford School in New York City, where she served as Associate Head of School since 2013. Prior to that, she was Associate Dean of Faculty at The Taft School in Watertown, CT where she spent twelve years.

Since coming to Vermont Academy, Jennifer has worked with the board and the school community to launch a new strategic plan. She has led the campaign that drives the plan to significant gains, with record breaking fundraising in 2020 and a near doubling of that amount in 2021. Part of this success comes from significant initiatives to engage alumni by clarifying the school’s identity, purpose, direction, and value proposition. She has also overseen several partnerships, including with Liceo Europeo in Madrid, Spain, where students enrolled in the international education program now receive a Vermont Academy diploma, and a partnership with Mount Snow Academy to allow top-level sports-on-snow students to earn a Vermont Academy diploma.

During her tenure at Nightingale, Jennifer led new initiatives with vision, innovation, and results, including the development of the Nightingale Summer Academy; ongoing work on an eight-day rotational schedule; strategically utilizing new spaces to meld programming with design; and a campaign for global education. She managed strategic internal change, including STEM/STEAM curriculum, design thinking and coding initiatives, and innovative uses of spaces.

Jennifer taught English for many years at Taft, winning several teaching honors. She was appointed Mid Class Dean, leading 65-75 students each year, followed by being named English Department Head and then Associate Dean of Faculty.

A native of Connecticut, Jennifer graduated from Trinity College with a Bachelor of Arts degree in English and a Master of Arts degree in English with distinction. She received her doctorate in English from the University of Connecticut, where she graduated with honors.