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Head of Upper School: Leadership in Student Experience

Listing for: Winsor School
Full Time position Listed on 2026-11-14
Job specializations:
Salary/Wage Range or Industry Benchmark: 175000 - 210000 USD Yearly USD 175000.00 210000.00 YEAR

Job Description & How to Apply Below

The Winsor School in Boston invites applications for the Head of Upper School. This is a full‑time Administration role overseeing grades 9–12, partnering with the head of school and senior leadership to shape strategy, academics, and student life.

We seek a collaborative leader with deep commitment to girls’ education, equity, and belonging, who can build strong relationships with faculty, students, families, and the wider Boston community.

Consider building your career as a Head of Upper School:
Leadership in Student Experience at Winsor School.

This role, Head of Upper School:
Leadership in Student Experience at Winsor School, could be your next career step.

Are you ready to take on the Head of Upper School:
Leadership in Student Experience role at Winsor School?

We would love to welcome a new Head of Upper School:
Leadership in Student Experience to our organisation in Boston, MA, United States.

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