15 Greater Boston Independent School Leaders to Know

Last updated: August 2026

Greater Boston has a rich mix of independent schools, from early learning communities to long established day and boarding schools. This guide introduces 15 current school leaders, including one interim head, whose work helps shape that landscape.

Each school has its own mission, age range and community. What these leaders share is responsibility for the conditions in which students, families and staff can do their best work.

For families and school partners, a directory is only a starting point. The school links in each profile offer current detail from the school itself.

Why independent-school leadership matters

Independent-school leaders make choices about culture, learning, community partnerships and the practical habits of school life. Those choices matter because they affect how students experience school each day.

Strong leadership is both human and operational. It asks people to build trust while making clear decisions about what happens next.

1. Alixe Callen

Head of School, Milton Academy

Alixe Callen leads Milton Academy in Milton. Her role brings together academic direction, staff leadership and the confidence of families across a large school community.

In January 2026, Milton shared a new lower and middle school leadership structure under Callen's leadership. Clear roles can help adults make good decisions close to students.

2. Allison Webster

Head of School, Dedham Country Day School

Allison Webster is Head of School at Dedham Country Day School in Dedham. Her school biography describes a career centred on students, families and school communities.

Webster holds a Master of Applied Positive Psychology and an Ed.M. from Harvard Graduate School of Education. That background fits the close attention to relationships and learning that young school communities need.

3. Bill Wharton

Interim Head of School, The Advent School

Bill Wharton is Interim Head of School at The Advent School in Boston. The school appointed him for the 2025 to 2026 and 2026 to 2027 school years while it works through a leadership transition.

Before Advent, Wharton served as Head of School at Commonwealth School in Boston's Back Bay for more than 20 years. His experience gives Advent a steady leader during an important period of change.

4. Brendan Largay

Head of School, Belmont Day School

Brendan Largay is Head of School at Belmont Day School in Belmont. The school serves children through the middle years, when consistency between home, classroom and school leadership is especially important.

Largay's school biography notes his service on the Association of Independent Schools in New England board. That work connects the daily life of one school with wider conversations across independent education.

5. Catherine J. Hall

Head of School, Noble & Greenough School

Catherine J. Hall is Head of School at Noble & Greenough School in Dedham. Nobles describes its purpose as inspiring leadership for the public good.

That purpose becomes useful when it shapes ordinary choices about learning, relationships and community expectations. A clear purpose gives a school a shared reference point when decisions are hard.

6. Gregory J. Schneider

Head of School, Belmont Hill School

Gregory J. Schneider is the Ronald M. Druker '62 Head of School at Belmont Hill School. He has led the school since 2018, following eleven years as head of Berwick Academy.

Belmont Hill serves boys in Grades 7 to 12. Schneider's experience across two schools gives him a practical view of how tradition and ongoing learning can sit together.

7. Henry D. Fairfax

Head of School, Concord Academy

Henry D. Fairfax is Head of School and the Dresden Endowed Chair at Concord Academy in Concord. He became the school's eleventh head in 2022.

Before Concord Academy, Fairfax was the founding head of Revolution School in Philadelphia. Building a school from its early stages calls for attention to both mission and the systems that make it real each day.

8. Jennifer Price

Head of School, Buckingham Browne & Nichols

Jennifer Price is Head of School at Buckingham Browne & Nichols in Cambridge. The school's leadership team spans teaching and learning, operations, enrolment, student support and community work.

That is a useful reminder that a school leader does not work alone. The job includes helping different kinds of expertise move in one clear direction.

9. Judy Guild

Head of School, Brimmer and May School

Judy Guild is Head of School at Brimmer and May School in Chestnut Hill. Brimmer has announced that she will finish the 2026 to 2027 school year after 14 years as head and 36 years as an educator and administrator.

Her long service is a reminder that leadership also includes leaving a community ready for its next chapter. A thoughtful transition can protect both the people who remain and the purpose they share.

10. Julie Porrazzo

Head of School, The Newman School

Julie Porrazzo became Head of School at The Newman School in Boston on 1 July 2026. She had served as the school's assistant head from 2023 to 2026.

Newman describes itself as an International Baccalaureate school in the city. Porrazzo's previous role gave her a broad view of the school's academic and student-life work before taking on the headship.

11. Lise Charlier

Head of School, The Cambridge School of Weston

Lise Charlier is Head of School at The Cambridge School of Weston. She joined the school in 2019 and also serves as president of the Association of Independent Schools in New England board.

The Cambridge School of Weston is a gender-inclusive day and boarding school for Years 9 to 12. Charlier's school and sector roles connect the daily work of one community with the wider independent-school landscape.

12. Mark J. Stanek

Head of School, Shady Hill School

Mark J. Stanek leads Shady Hill School in Cambridge. He joined the school in 2010 and has written the second edition of The Middle School Handbook for the National Association of Independent Schools.

His work is relevant to people interested in the transition from childhood to adolescence. The structures around young learners can make a real difference to their confidence and sense of belonging.

13. Meredith Legg

Head of School, The Winsor School

Meredith Legg is Head of School and O'Donnell Family Chair at The Winsor School in Boston. She began the role on 1 July 2025.

Winsor is a school for girls, and Legg's biography describes a commitment to girls' education. Her background in civil engineering also brings a systems perspective to the leadership conversation.

14. Ryan S. Dahlem

Head of School, The Rivers School

Ryan S. Dahlem has been Head of School at The Rivers School since 1 July 2023. He is the ninth person to hold the role.

Before Rivers, Dahlem worked at St. Margaret's Episcopal School, where he created a student-centred innovation strategy. Innovation is most useful in schools when it keeps students and relationships in view.

15. Tara Hofherr

Head of School, Kingsley Montessori School

Tara Hofherr is Head of School at Kingsley Montessori School in Boston. Kingsley's current school page describes her as a leader who has spent more than a decade in the community.

Continuity can be valuable when a school wants to carry forward its character while responding to new questions. It gives a leader a close understanding of the relationships that make the school work.

What these leaders show us about independent-school leadership

The profiles point to a simple pattern. Good school leadership is about the quality of conversations, the clarity of roles and the daily choices that help students feel known.

Clear expectations matter. When leaders say what good looks like, people can act with more confidence. When they make ownership visible, important work is less likely to drift between well-meaning people.

The same principle applies across school types. A Montessori school, a boarding school and a large day school will have different rhythms, but each benefits when adults can name the real decision and agree on the next practical move.

Conclusion

Independent schools are shaped by far more than the person at the top, yet a head of school has an important role in setting the conditions for good work. The leaders here represent different communities and stages of schooling, but each is responsible for helping people learn, contribute and belong.

If you are exploring a school, keep your questions practical. Ask how decisions are made, how students are known and how the school helps adults work through difficult moments.

The most useful leadership ideas are the ones people can use on Monday morning. Start with one conversation, one expectation or one decision that needs more clarity, then make the next move small enough to begin.

Related Reading

For school-focused leadership support, read 31 Best Leadership Development Experts for Schools.

For a practical team conversation, read Working Genius for executive teams.

Build a stronger school leadership team

I help leaders build organisations people would move cities to work at. If your school leadership team needs a practical keynote, workshop or facilitated leadership session, email jonno@consultclarity.org.

About the Author

Jonno White is a Brisbane-based leadership consultant, keynote speaker and Certified Working Genius Facilitator, and the author of Step Up or Step Out. He works with schools, corporates and nonprofits around the world. To enquire about a keynote, workshop or facilitated leadership session, email jonno@consultclarity.org.