
Drew Casertano
“As Headmaster, Drew was ever thoughtful in his governance—leading by example, collaborating with trustees and faculty at all levels, and building talented teams with a shared vision.”
Drew Casertano has devoted his professional life to serving students and their families as an independent school educator and leader. After earning a Master of Education degree from Harvard University in 1982, Drew spent two years at The Frederick Gunn School (formerly The Gunnery) as director of admission and financial aid, before returning to Loomis Chaffee as the director of admission and financial aid for five years.
In 1990, Drew was appointed as Millbrook School’s sixth headmaster and continued in that role until June 2021. In those 31 years, applications tripled, the enrollment grew from 170 to 330, the endowment increased from $6,000,000 to nearly $70,000,000, and annual and capital funds of $200,000,000 million were raised to support more than 223,000 square feet of new and renovated spaces.
Drew also has important experience as an independent school trustee, having served on the boards of Dutchess Day School, Indian Mountain School, New Canaan Country School, and Washington Montessori School, as well as the Parents League of New York, the Secondary School Admission Test Board (now the Enrollment Management Association) and The Association of Boarding Schools (TABS). In addition, he was president of the board of the New York Association of Independent Schools (NYSAIS) and president of The Heads and Principals Association.
In 2019, The Association of Boarding Schools honored Drew with the Ruzicka Compass Premier Leadership Award, which recognizes extraordinary contributions to the excellence, advancement, and success of boarding schools.
Drew joined Strategic School Leadership because he believes deeply in its mission to serve “school leaders so their schools may thrive.” His approach to coaching is Socratic and grounded in his deep desire to support heads of school as they care for and provide the moral, spiritual, and strategic leadership for their schools in these increasingly complex and challenging times. His long service as Millbrook’s headmaster and as an independent school trustee leave Drew uniquely qualified to support heads as they “manage up” to their boards and build effective leadership teams on campus. Given his success in increasing enrollment at Frederick Gunn, Loomis Chaffee and Millbrook, Drew can help schools address the existential challenge of a declining enrollment. He is equally prepared to support board chairs and boards as they do the all-important work of governing the school and build effective leadership teams. Based on hard earned experience, he can assist with crisis management.
Certified to lead school leaders through the Return on Character® Assessment, Drew has been privileged to guide heads of school and other senior administrators through this powerful and valuable process that enables them to leverage their leadership character for better performance.
Drew’s partial client list includes Dana Hall School, Deerfield Academy, Durham Nativity School, Girls Preparatory School, Grace Church School, Hebron Academy, Morristown Beard School, New Canaan Country School, Oak Hill School, Randolph School, Right To Dream Academy, Waterside School, Westminster School, and Woodlands Academy of the Sacred Heart.