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Elizabeth “Bessie” Cromwell Speers ’86 is the head of Middlesex School in Concord, Massachusetts. Appointed in July 2023, she has more than three decades of experience in independent school education, including 15 years as a head of school. In her previous position as head of Tower Hill School in Wilmington, Delaware, she was the first woman to hold the senior leadership position. Before Tower Hill, Speers was head of the Ethel Walker School in Connecticut, where she oversaw programmatic advancements, investments in technology, and a successful $50 million centennial campaign. Her prior appointments include assistant head of school at Episcopal Academy outside Philadelphia; director of placement and strategic planning at Calvert School in Baltimore; director of admissions and financial aid at the Bryn Mawr School in Baltimore; and associate director of admissions at Loomis Chaffee School in Connecticut. An English major at Middlebury, Speers holds a Master of Liberal Arts degree from Johns Hopkins University, and in 2014 she was a Klingenstein Fellow at Columbia University’s Teachers College. In July 2023 Speers will assume the role of head of school at Middlesex in Concord, Massachusetts.