Head of School

Lead a growing school. Inspire a community. Shape what comes next.

Ashwood Glen School is seeking an experienced and collaborative Head of School to lead our school community through its next stage of growth.

Serving children from Montessori Early Years through Grade 8, Ashwood Glen combines a strong academic foundation with inquiry, creativity, and personalized learning. We are an IB Primary Years Programme World School and an IB Middle Years Programme Candidate School.

Working closely with the Director, the Head of School will provide leadership across academics, operations, people, finance, compliance, and enrolment. This is an opportunity for a leader who can translate vision into action, develop strong teams, and build lasting relationships with students and families.

The Role

School Leadership and Operations

• Lead daily operations, ensuring a safe, welcoming, and well-organized school environment.
• Guide the leadership and administrative teams through clear priorities, effective planning, and consistent follow-through.
• Oversee staffing schedules, timetables, the school calendar, facilities coordination, and resource allocation.
• Ensure successful delivery of school events, extracurricular activities, athletics, and enrichment programmes.
• Strengthen operational systems and ensure timely, effective communication with families.

Academic Excellence

• Work with Divisional Heads and Curriculum Coordinators to strengthen teaching, learning, and student outcomes.
• Support consistent implementation of Montessori practices, IB programme standards, and applicable Ontario curriculum expectations.
• Use assessment information and student progress to guide school improvement.
• Coach and develop instructional leaders and promote meaningful professional learning.
• Lead the annual School Improvement Plan, including measurable goals and regular progress reviews.

Student and Family Experience

• Build a school culture grounded in wellbeing, belonging, respect, and academic achievement.
• Oversee student support, behaviour, attendance, and wellbeing systems.
• Address complex parent concerns with empathy, sound judgment, and clear communication.
• Strengthen parent partnerships, student leadership, school spirit, and retention.
• Lead parent engagement initiatives and support a positive experience throughout each family’s journey.

People and Culture

• Attract, develop, and retain exceptional faculty and staff.
• Lead performance reviews, coaching, employee relations, and succession planning.
• Establish clear expectations and a culture of collaboration, accountability, and continuous improvement.
• Oversee HR policies and practices in partnership with the Director and HR Coordinator.

Governance, Compliance, and Accreditation

• Oversee regulatory compliance, Ministry reporting, inspection readiness, and school policies.
• Lead IB programme evaluation and authorization work, alongside relevant academic leaders.
• Maintain effective relationships with regulatory agencies, accreditation bodies, and educational organizations.

Financial Stewardship and Growth

• Develop and manage the operating budget in collaboration with the Director.
• Align staffing and spending with educational priorities and long-term sustainability.
• Guide admissions, enrolment growth, and retention strategies.
• Partner with Marketing on campaigns, Open Houses, and community outreach.
• Represent Ashwood Glen and develop partnerships that strengthen the school’s reputation and opportunities.

What You Bring

• Demonstrated leadership experience in a school setting, ideally as a Head of School, Principal, Vice-Principal, or Divisional Head.
• A degree in education or a related field; a postgraduate qualification in educational leadership is an asset.
• Strong knowledge of curriculum, assessment, instructional leadership, and student wellbeing.
• Experience with IB programmes; familiarity with Montessori education is an asset.
• An understanding of Ontario’s educational and regulatory environment.
• Experience leading teams, managing operations and budgets, and implementing improvement plans.
• Strong communication skills and the ability to navigate sensitive conversations with professionalism and care.
• A practical, proactive approach, with the ability to balance strategic priorities and daily responsibilities.

Why Ashwood Glen?

You will have the opportunity to influence the direction of a growing school, work closely with its founder and leadership team, and strengthen an educational journey that connects Montessori foundations with IB learning.

We are looking for someone who shares our commitment to helping children feel known, supported, and challenged and who brings the leadership to make that commitment visible every day.

How to Apply

Please apply through LinkedIn or at hr@ashwoodglen.com with your resume and a cover letter outlining your leadership experience and interest in Ashwood Glen.