Head of School
Head of School – Williamsburg Montessori School
Apply by: April 30th, 2026
Application link: bit.ly/wmsheadofschool
Applications reviewed on a rolling basis
Location: Williamsburg, VA
Reports to: Board of Trustees
Start Date: August 2026
About Williamsburg Montessori School
Williamsburg Montessori School (WMS) is a nurturing, dynamic, and values-driven learning environment that serves students from toddler through middle school. Rooted in the Montessori philosophy, WMS empowers independent thinking, self-directed learning, and compassionate leadership. We are seeking a Head of School who can continue this legacy while embracing the Montessori tradition and leading the school into its next chapter of strategic growth, visibility, and community impact.
WMS is located in Williamsburg, VA, a spectacularly beautiful city centrally located to the coast and the Virginia state capital.The nearby James and York rivers flow majestically to the Chesapeake Bay. It is an important part of Virginia's Historic Triangle including Yorktown and Jamestown. The College of William and Mary, Colonial Williamsburg, a nationally recognized library system, and numerous state and national parks enrich the lives of its residents.
WMS At-A-Glance:
- Started in 1982
- 16 faculty, 16 staff
- 134 students
- 2 campus locations
- 8 classrooms
- 501(c)3 non-profit
- Member school with AMS and NAIS
Position Summary
The Head of School (HOS) is the strategic and operational leader of Williamsburg Montessori School. As the sole employee of the Board of Trustees, the HOS is responsible for the overall leadership and administration of the school, with a strong emphasis on community engagement, enrollment growth, and external relations. The HOS is expected to be a visible, inspiring presence within and beyond the school community, cultivating strong relationships with families, faculty, donors, and the greater Williamsburg area.
For full job description:
To Apply
Interested candidates should submit the following at bit.ly/wmsheadofschool:
- Resume or CV
- Thoughtful cover letter outlining fit for the role and connection to Montessori education
- Contact information for 3 professional references
Applications will be reviewed on a rolling basis, but must be received by April 30th, 2026 to be considered. Please direct any questions to [email protected]
