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Milton Academy Leadership

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At Milton Academy, our dedicated administration, faculty, and board of trustees are just as inspiring as our students.

In fact, many of them, including our Head of School, attended Milton themselves. Guided by a shared commitment toward academic excellence, student well-being, and inclusive values, our leadership team helps create a dynamic environment where young people are known, supported, and inspired to thrive.

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Alixe Callen '88
Milton Academy Head of School

Dr. Alixe Callen, a Milton Academy graduate with extensive teaching and leadership experience in both public and independent schools, began serving as Milton’s 13th head of school in 2023.

A lifelong educator committed to the pursuit of excellence and innovation in teaching, Dr. Callen balances a wealth of experience as well as an ability to look into the future and navigate changes in pedagogy and education. She champions student-centered curriculum development, a collaborative approach to leadership, and enthusiasm for building community across the school’s three academic divisions. Dr. Callen has supported  Milton’s intentional, deeply held commitment to building a diverse and inclusive community that fosters an understanding of injustice and a common goal of fair, equitable practices for all.

Independent schools have the power to demonstrate exceptional leadership in education—embracing the cutting edge of teaching and learning while remaining committed to the high academic standards they have held for generations. Dr. Callen strongly believes that the transformative work happening at Milton Academy can and should extend beyond the boundaries of its campus. In 2024, she launched the school’s next strategic planning process with the goals of preparing students to meet the opportunities and challenges of a rapidly changing world.  

Prior to Milton, Dr. Callen was head of school at St. George’s School in Middletown, Rhode Island, a position she held from 2017 to 2023. During her time there, she and her team undertook a full-scale effort to review and renew the school’s curriculum to support interdisciplinary and connected learning, prioritizing strong academics and reflecting the latest research in education.

Dr. Callen received her bachelor’s degree in American civilization from Brown University, a master of arts in teaching degree from Brown, a master’s degree in administration, planning, and social policy from Harvard University, and her doctorate from Harvard, where she was elected to the Harvard Educational Review. 

Before becoming head at St. George’s, Dr. Callen was the upper school director at Lakeside School in Seattle, the principal of Acton-Boxborough Regional High School in Acton, Massachusetts—a 2,000-student public school consistently rated among the best in the state—and assistant principal of Needham High School in Needham, Massachusetts. She has also held leadership, teaching, and research positions through the Harvard Graduate School of Education, the Francis W. Parker Charter Essential School in Devens, Massachusetts, the Sedona-Oak Creek Unified School District in Sedona, Arizona, and the Coalition of Essential SchoolsShe and her husband, James Bailey, have two sons, Zander and Miles.

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Milton Academy Administration

Steven Bertozzi

Principal, Lower and Middle Schools

Vanessa Cohen Gibbons

Chief Equity and Inclusion Officer

Kelly DeGregorio

Chief Advancement Officer

Mark Heath

Chief of Staff, Director of Strategic Initiatives

Eileen Newman

Chief Communications Officer

Paul Rebuck

Dean, Enrollment and Financial Aid

Rachel Stone

Principal, Upper School

Susika Wylie

Chief Legal Counsel

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Milton Academy Board of Trustees

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Claire Hughes Johnson '90 P '24 '27
President
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Bradley M. Bloom P '06 '08
Emeritus
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David Brewster '90 P '25 '30
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David Cappillo P ’20 ’24 ’26
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Jason Dillow '97
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Lisa B. Donohue '83 
Emerita
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Rana el Kaliouby P ’21 ’27 
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Shadi Farokhzad P ’23 ’25 
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Yeng Felipe Butler ’92 P ’25 ’33
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John B. Fitzgibbons '87 
Treasurer
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Lamont Gordon '87
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Yvonne Hao P ’28
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Franklin W. Hobbs, IV '65 P '98
Emeritus
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Sonu Kalra P ’23 ’26 ’28
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Molly King
 
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Molly Ladd ‘92 P '22 '25 '30
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Bill Lee P ’98 ’00 GP ’30 ’32
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Jean Liu P ’28
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Ted Maloney '96 P '32
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Osaremen Okolo ’13
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Adam Portnoy ’89 P’25
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Kevin Prussia P '32 '34
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Tom Reardon ’92 P ’26 ’28 '32
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Gene Reilly ’79 P ’10 ’12
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Hendrick Sin P ’23 ’25 ’27
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Gabriel Sunshine P ’22 ’24
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Patrick Tsang ’90 P ’27 ’27
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Diana Vogel ‘86 P '21 '23 '25
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Justin Walsh ’99
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Caleb Weinstein P ’26
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Helen Zhu P ’25