Head of School

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.

• Champion the mission, values, and Montessori philosophy of WMS.
• Collaborate with the Board to define and implement strategic priorities, especially in the areas of enrollment growth, financial sustainability, and program development.
• Create a positive, inclusive culture that supports collaboration, curiosity, and continuous improvement.

• Supervise and support the Director of Education and faculty in maintaining excellence in Montessori instruction and curriculum.
• Champion child-centered, developmentally aligned practices across all program levels (Toddler through Middle School).
• Promote professional development and mentoring to ensure instructional quality and staff retention.

• Serve as the chief ambassador and spokesperson for WMS in the broader community.
• Lead the development of a comprehensive marketing and branding strategy that strengthens the school’s visibility, enrollment, and fundraising capacity.
• Oversee internal and external communications to ensure clarity, consistency, and engagement with key stakeholders.
• Collaborate with the Board and development committee on annual and long-term fundraising strategies, including donor stewardship and event-based fundraising.

• Foster a warm, welcoming school culture for families, students, faculty, and staff.
• Build meaningful partnerships with local organizations, alumni, and parent groups.
• Lead initiatives and public events that showcase WMS’s programs and values.

• Oversee and refine the admissions and enrollment processes, with a focus on reaching full enrollment across all programs.
• Utilize data to monitor enrollment trends and adjust outreach and retention strategies accordingly.
• Work closely with faculty and administrative staff to ensure a smooth and personalized admissions experience for prospective families.

• Oversee the school’s operations and supervise administrative staff with efficiency, transparency, and foresight.
• Work closely with the Board Finance Committee to develop and manage the annual budget and long-term financial planning.
• Oversee compliance with state licensing, accreditation, and safety requirements.
• Provide clear and timely reporting to the Board and serve as liaison between the Board and the school community.

• Bachelor’s degree (Master’s degree strongly preferred)
• Minimum of 5–7 years in educational leadership, preferably within a Montessori or independent school
• Demonstrated experience in enrollment management, marketing, or development
• Strong communication and relationship-building skills
• Proven ability to lead teams, manage change, and align operational and strategic goals
• Deep respect for the Montessori philosophy and the ability to lead a Montessori school with integrity

• MACTE Montessori certification
• Experience with small or mid-sized independent school leadership
• Familiarity with state licensing and accreditation processes
• Previous experience working with a nonprofit board

for more information.