Gulliver Appoints Dr. Tom Milaschewski as Next Head of School

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Gulliver Preparatory School is pleased to announce the appointment of Dr. Tom Milaschewski as its next Head of School, effective July 1, 2026.

Following a comprehensive national search, Dr. Milaschewski was selected for his deep commitment to instructional excellence, student well-being, and leadership that strengthens both academic outcomes and community culture. He brings to Gulliver a track record of guiding schools through periods of growth and change with clarity, care, and purpose.

“We are thrilled to welcome Tom to Gulliver,” said Gulliver’s President, Simon Hess. “He is an educator whose values, vision, and leadership align powerfully with our commitment to Next-Level Teaching and Learning and to nurturing Thriving Students. Tom’s arrival ensures continuity of excellence as we build on Gulliver’s extraordinary legacy and look ahead to Gulliver’s next chapter.”

Tom joins Gulliver from Reading Public Schools in Massachusetts, where he currently serves as Superintendent, leading a high-performing district of more than 4,000 students and 800 faculty and staff across nine schools. Under his leadership, the district has advanced outcomes in literacy, STEM, college readiness, and innovative career pathways spanning computer science, engineering, healthcare, and the arts.

A former teacher and principal, Tom is widely recognized for his collaborative leadership style, ability to build strong partnerships with families and boards, and focus on empowering educators to do their best work on behalf of students. His approach reflects Gulliver’s belief that success is measured not only by what students achieve, but by who they become along the way.

“I’ve been incredibly impressed by the people in this community and the shared sense of purpose that connects them, along with the care shown for students,” said Tom. “Gulliver is a unique and deeply credible institution with an outstanding reputation, and I’m excited to begin listening, learning, and forming relationships as we carry forward the school’s strong foundation and proud traditions.”

Tom earned his doctorate from the Harvard Graduate School of Education and has dedicated his career to building learning environments where high expectations, care for the whole child, and a strong sense of belonging go hand in hand. Throughout his career, he has focused on creating school communities where students are both well supported and challenged to grow. His leadership reflects a belief that strong outcomes are built through aligned instruction, meaningful relationships, and a culture where students and educators alike can thrive.

Tom and his wife, Sarah, are the parents of five children: Makenna (12), Olivia (10), Jocelyn (8), Benjamin (6), and Grace (4). The Milaschewski family is excited to make Miami home and to begin this next chapter with the Gulliver community.

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