Head of School

Williamsburg, Virginia

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.

Key Responsibilities

• Leadership & Strategy

• 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.

Educational Leadership

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.

Marketing, Communications & Advancement

• 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.

Community Engagement

• 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.

Enrollment & Admissions

• 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.

Operations & Finance

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.

Qualifications

Required:

• 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

Preferred:

• AMI or AMS 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

Compensation & Benefits

Compensation is competitive and commensurate with experience. Benefits include paid time off, health insurance, professional development, and more. Details will be shared during the interview process.

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 wmsheadofschoolsearch@gmail.com