Upper School Leader & Assistant Head of School

CAIS; Canada; On-site; CAD 160,000 - 190,000; Full time

Job summary

St. Anne’s School in Canada seeks an experienced leader to serve as Assistant Head of School, Director of Upper School, reporting to the Head of School. The appointment will be effective August 1, 2027.

The role focuses on strategic direction, day-to-day leadership, and growth of the Upper School program, including student life, policies, and faculty development. Evening events and travel are required; commitment to an all-girls learning environment is essential.

Qualifications

• Master’s degree in education and Ontario Principal’s Qualifications, or equivalent preparation.
• Demonstrated academic, operational, and school-wide leadership experience.
• Excellent knowledge of the Ontario curriculum and girls’ education in an all-girls environment.
• Proven ability to lead people and programs with integrity, empathy, and sound judgment.
• Strong communication, relationship-building, conflict-resolution, organizational, and problem-solving skills.
• Experience in independent or girls’ schools is an asset.
• Role requires some evening/weekend events and travel.
• Maintain high professionalism, discretion, student safety and confidentiality.

Responsibilities

• Provide leadership and oversight for Upper School programming, student life and daily operations.
• Support development and implementation of strategic initiatives, policies, handbooks, and schedules.
• Lead, mentor and support faculty; collaborate with academic leaders to strengthen teaching and program development.
• Build trusted relationships with students, families, employees and partner schools.
• Oversee student well-being, leadership, discipline, and activities.
• Partner with Admissions on applicant review and enrolment-related events.
• Contribute to co-curricular program and teach one section.

Skills

School leadership

Strategic thinking

Communication

Relationship-building

Problem-solving

Education

Master’s degree in education

Ontario Principal’s Qualifications

Job description

St. Anne’s School in Canada seeks an experienced leader to serve as Assistant Head of School, Director of Upper School, reporting to the Head of School. The appointment will be effective August 1, 2027.

The role focuses on strategic direction, day-to-day leadership, and growth of the Upper School program, including student life, policies, and faculty development. Evening events and travel are required; commitment to an all-girls learning environment is essential.