Head of School

GLOUCESTER MONTESSORI SCHOOL

HEAD OF SCHOOL

Gloucester, Virginia | Salary: $40,000-$55,000

Lead with purpose. Nurture potential. Strengthen community.

Gloucester Montessori School (GMS) seeks a collaborative, mission-driven Head of School (HOS) to lead our non-profit school community and guide its continued growth. This is an opportunity for an experienced educational leader who believes in the potential of every child, values Montessori principles, and understands the importance of strong relationships among students, families, faculty, staff, and the Board of Directors.

The Head of School serves as the school’s central administrative leader, championing its mission while overseeing daily operations, supporting educational excellence, stewarding financial resources, and helping shape the school’s long-term future.

About the role

Reporting directly to the Board of Directors, the Head of School is responsible for the overall administrative success and well-being of Gloucester Montessori School. The Head provides strategic direction and operational leadership while fostering a safe, respectful, and welcoming environment where children and adults can thrive.

The successful candidate will balance big-picture planning with hands-on leadership, bringing sound judgment, strong organizational and communication skills, and a genuine commitment to Montessori education.

Key responsibilitiesSchool leadership and operations

• Oversee the daily operation and administrative success of all school programs, maintaining a safe, welcoming environment for students, families, faculty, and staff.
• Ensure school operations comply with applicable laws and regulations and maintain accurate student, staff, and prospective-student records.
• Coordinate school functions and activities and oversee facilities, grounds, equipment, security, maintenance, and operational expenditures within budget.
• Build a strong management team, delegate effectively, and foster clear, constructive communication across the school community.

Educational leadership and Montessori philosophy

• Promote and carry out the mission of GMS and ensure that curriculum, instruction, and prepared environments reflect Montessori philosophy and child-centered goals.
• Work with Head Teachers to coordinate curriculum, support educational goals, and promote consistency and integration across classrooms.
• Conduct periodic classroom visits and personnel reviews to support educational standards, professional growth, and quality instruction.
• Maintain a respectful school culture grounded in grace, courtesy, and consistent, respectful discipline; serve as a liaison between teachers and parents when classroom issues arise.

Staff leadership and development

• Responsible for the recruitment of teaching staff and non-teaching personnel in consultation with the Board, as appropriate.
• Develop and administer equitable personnel practices related to compensation, working conditions, discipline, training, and professional development.
• Establish clear performance expectations, provide coaching and guidance, and address personnel concerns constructively and appropriately.
• Promote positive, productive working relationships among all employees.

Strategic planning and financial stewardship

• Collaborate with the Board, senior staff, and parents as appropriate to establish and implement short- and long-term goals for financial stability, enrollment, facilities, and educational performance.
• Work closely with the bookkeeper and Board Treasurer on financial planning and communication of Board policies and decisions.
• Research, apply for, and administer grants; lead and implement fundraising plans and giving programs in partnership with the Board, fundraising leaders, and parent volunteers.
• Develop and monitor measurable indicators of school performance and stay informed about educational research, Montessori trends, and legislation affecting independent schools.

Enrollment, communications, and community relations

• Represent the GMS mission to prospective families and oversee student recruitment, admissions, enrollment policies, and related processes.
• Oversee internal and external communications, including newsletters, website, social media, and promotional events.
• Serve as spokesperson for the school and represent GMS in the wider community and with other educational institutions and associations.

Board partnership

• Serve as a non-voting member of the Board of Directors and attend Board meetings and functions.
• Keep the Board Chair informed about school operations and bring forward issues requiring Board action, policy review, or Board education.
• Provide recommendations and serve as a resource for strategic planning, policies, and initiatives, while communicating and implementing Board decisions with the school community

REQUIRED QUALIFICATIONS:

• The HOS must meet all educational/experience requirements outlined in .
• Strongly aligned with Montessori principles and a willingness to complete training regarding Montessori practices as determined by the Board.
• Outstanding organizational and communication skills.
• Ability to work harmoniously with parents, teachers, and students.
• Pass Criminal Background check, pre-employment drug screen, and VDSS Background Check

PREFERRED QUALIFICATIONS:

• Minimum of 5-10 years combined experience as a head of school, teacher and/or director/administrator in education of children ages two to fourteen, preferably in a Montessori setting.
• Management experience and strong leadership skills.
• Strong fiscal literacy and experience navigating non-profit budgeting.
• Background in fundraising, donor cultivation and/or community development.

BENEFITS

• Generous paid time off
• Tuition discount
• Opportunities for professional growth and education

How to apply

Interested candidates are invited to submit a résumé and cover letter describing their relevant experience, leadership approach, and connection to Montessori education. Please send application materials to gmsboardofdirectors@gmail.com.

Pay: $45,000.00 - $55,000.00 per year

Benefits:

• Paid time off
• Professional development assistance
• Retirement plan

Application Question(s):

• Do you meet the minimum educational/experience requirements for a Program Director as listed in 8VAC20-780-190

https://law.lis.virginia.gov/admincode/title8/agency20/chapter780/section190/

Work Location: In person