Head of Upper School: Leadership in Student Experience

Winsor School; Boston (MA); On-site; USD 175,000 - 210,000; Full time

Job summary

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.

Qualifications

• Proven track record in K-12 leadership
• Experience in curriculum development
• Commitment to diversity, equity and inclusion

Responsibilities

• Oversee Upper School (grades 9–12) and partner with senior leadership to shape strategy, academics, and student life.
• Foster a collaborative and inclusive environment for students, faculty, and families.
• Lead initiatives that align with Winsor's mission and community values.

Job description

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.