An independent school educator and leader for more than 40 years, Drew Casertano has devoted his professional life to serving students, families, and schools. A graduate of Choate, Amherst College, and Harvard University, Drew began his career as a teacher, coach, and administrator at Loomis Chaffee and The Gunnery before being appointed Millbrook’s sixth headmaster in 1990.

 

During his 31 years as headmaster, Millbrook experienced extraordinary growth and transformation. The applicant pool tripled, enrollment increased from 170 to 330 students, the endowment grew from $6.7 million to $70 million, and nearly $150 million in capital funds were raised. Working in close partnership with the board of trustees, Drew oversaw the construction of major facilities—including Mills Athletic Center, Holbrook Arts Center, Hamilton Math and Science Center, Koenigsberger Hall, and a new dining hall, Casertano Hall—as well as significant renovations to dormitories, the historic Barn, and other campus spaces.

 

Beyond Millbrook, Drew has held leadership roles across the independent school world. He served on the boards of The Association of Boarding Schools (TABS) and the New York Association of Independent Schools (NYSAIS), and as board president of NYSAIS and of the Heads and Principals Association. His trusteeship experience also includes Dutchess Day School, Indian Mountain School, New Canaan Country Day School, and Safe Passage, a nonprofit serving children in Guatemala City.

 

In 2021, Drew joined Strategic School Leadership as a partner, advising boards and school leaders on governance, leadership development, enrollment challenges, and crisis management. In 2025, he assumed the role of co-managing partner. Guided by a Socratic coaching approach, he remains deeply committed to helping school leaders—and their schools—thrive.