“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.
“There is much to say that is wonderful about Drew Casertano and the wisdom, experience, and compassion that he brings to this work. While he has worn many hats in his career, he has never fully taken off the hat that brought him to the work initially–that of teacher. Whatever the task in front of him, Drew is always the educator who is thinking about the end goal and then carefully designing an approach and offering support that builds skills, strengthens alignment, boosts confidence, and reinforces the mission of the school. He understands the value of asking the right question and allowing his clients to find the answers that best fit their needs and the needs of the school.“Elaine White,
Head of School, Westminster School
“In my role as board chair, Drew Casertano has been an invaluable partner as we’ve undertaken our latest strategic plan and navigated important conversations about how we evolve as a school to ensure that we remain competitive and continue to meet our mission in an educational landscape and world that’s driven by unprecedented change. We’ve benefited tremendously from Drew’s wise counsel, keen strategic mind, extraordinary emotional intelligence, governance expertise and many years of experience as an outstanding Head of School. Drew is an absolute pleasure to work with—and an incredible resource for any board or school leader.”Renee Carrel
Board Chair, Westminster School
“Drew Casertano is excellence personified. A magnanimous leader, mentor and friend whose success is derived, in part, from his innate ability to remain as focused on the end goal as the journey itself. As Headmaster for more than 30 years, Drew has successfully nurtured a culture of curiosity, creativity, and compassion at Millbrook. As he embarks on a new path, I am confident Drew will continue to excel and continue to inspire us to act with integrity and respect — to do better and be better, not only for ourselves but for the greater good of our communities.”Dean Dakolias
Millbrook parent ‘22 and trustee, Co-CIO Fortress Investment Group
“I have never met a Headmaster at any level who has done a better job heading a school in every way. Drew has that rare ability to be a visionary and strategic thinker, but also someone with a remarkable attention to detail. There are many qualities that are required to be a successful Headmaster, and Drew has excelled in all of them. Whether it is development, governance, team building, enrollment management, strategic and campus planning or advancement, Drew is second to none. I can easily envision him sharing his thorough knowledge of all these areas in the next chapter of his life. He is a man who wants to give back and to share his experience and perspective.”Sean McManus
Millbrook parent ‘18 and trustee, Chairman, CBS Sports
“Drew’s remarkable way of managing the many constituents of an independent school community is the result of his deep understanding of independent schools and the people affiliated with those institutions. Strategic, personable, and intentional, Drew took a school that was struggling with a deficit to a thriving and financially sound institution. I watched him do this skillfully as he led both the Board and the faculty, using different techniques and approaches to guide all to understand his vision and perform their appropriate tasks. I marveled at his ability to be fully present in the day-to-day life of the school, while also be fully engaged with the Board at a generative level and with alumni and friends of the school off campus. It seemed as if Drew had more than 24 hours in his day. As a Head of school, I still rely on Drew’s advice to navigate challenges at the Board level, as well as with daily operations. His exceptional emotional intelligence and strategic mindset, coupled with decades of experience, make him a valued resource.”Elizabeth Morrison
Head of School, Morristown-Beard School
“After 10 years of headship, I had the opportunity to work with Drew Casertano and Kelly Garramone through the Return on Character Assessment (ROC) and have found it to be the single most valuable professional development experience of my life. The nature of the assessment, from its theoretical underpinnings to its process and format, is thorough and relevant. Even more, the wisdom and personal attention and care that Kelly and Drew brought to each stage of the process helped me access the learnings as fully as I was able. Finally, Drew’s coaching as I focused on my Keystone Habit has been extraordinary in helping me shift to become a more effective leader. I feel energized for my next decade of leadership as a result of working with Drew and Kelly through the ROC.”Aaron Cooper, Head of School
New Canaan Country School