Head of Upper School - Visionary, Student-Centered Leader

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

Job summary

The Winsor School in Boston seeks a Head of Upper School to provide visionary, student‑centered leadership across grades 9–12, in partnership with lower school leadership. The role emphasizes collaboration with teachers, families, and the broader community to advance Winsor’s mission and strategic plan.

The successful candidate will steward academic excellence, diversity, equity and inclusion, mentor long‑tenured faculty, and ensure a cohesive experience across divisions while guiding

Job description

The Winsor School in Boston seeks a Head of Upper School to provide visionary, student‑centered leadership across grades 9–12, in partnership with lower school leadership. The role emphasizes collaboration with teachers, families, and the broader community to advance Winsor’s mission and strategic plan.

The successful candidate will steward academic excellence, diversity, equity and inclusion, mentor long‑tenured faculty, and ensure a cohesive experience across divisions while guiding