Upper School Director: Visionary Leadership & Growth

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

Job summary

The Winsor School in Boston seeks a dynamic Head of Upper School to lead the 5–12 program, overseeing advisory, student life, and the growth of Upper School divisions. This is a full-time Administration role reporting to senior leadership, with a strong focus on fostering an inclusive, rigorous, and supportive student experience.

The Head of Upper School will collaborate with the Head of School and Lower School leadership to ensure continuity, curricular alignment, and meaningful opportunities

Responsibilities

• Develop and implement a coherent experience for students across advisory, leadership development, and co-curricular programs.
• Strengthen transition and collaboration between Lower and Upper Schools.
• Lead faculty evaluation and professional growth with alignment to Winsor’s mission.
• Partner with senior leadership to advance Winsor’s strategic plan and ensure effective communication.

Job description

The Winsor School in Boston seeks a dynamic Head of Upper School to lead the 5–12 program, overseeing advisory, student life, and the growth of Upper School divisions. This is a full-time Administration role reporting to senior leadership, with a strong focus on fostering an inclusive, rigorous, and supportive student experience.

The Head of Upper School will collaborate with the Head of School and Lower School leadership to ensure continuity, curricular alignment, and meaningful opportunities