Assistant Head of School, Director of Upper 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 is a place of learning where girls are encouraged to find their centre, challenged to develop their voice, and pushed to explore and integrate beyond traditional norms. Empowering girls to be courageous learners and compassionate citizens who live and lead with wisdom, SAS serves young women in every capacity, providing an experience as unique and fulfilling as St. Andrew’s College has since 1899. Our students’ experiences will grow to become much richer as we construct and establish a progressive learning environment for generations to come. To find out more, visit our website at www.stannes.ca.

We invite applications for a leadership opportunity at St. Anne’s School in the role of Assistant Head of School, Director of Upper School, reporting to the Head of School. The appointment will be effective August 1, 2027.

St. Anne’s School is seeking an accomplished and collaborative educational leader to serve as Assistant Head of School, Director of Upper School. Working closely with the Head of School and as a key member of the Leadership Team, the successful candidate will help shape the school’s continued growth while providing strategic and day-to-day leadership for the Upper School program.

The Opportunity

This is a broad leadership role for an educator who brings sound judgement, creativity, and consistency to decision-making. The Assistant Head will champion the school’s vision, philosophy, and strategic priorities; foster a strong and inclusive culture for students, employees, and families; and support faculty in delivering an engaging, distinctive educational experience for girls.

Key responsibilities include:

• Providing leadership and oversight for Upper School programming, student life, and the daily operations of the school.
• Supporting the development and implementation of strategic initiatives, school-wide policies, handbooks, schedules, assemblies, duties, and major academic events.
• Leading, mentoring, and supporting faculty and collaborating with academic leaders to strengthen teaching, learning, professional growth, and program development.
• Building positive, trusted relationships with students, families, employees, colleagues at St. Anne’s School and St. Andrew’s College, and the broader independent-school community.
• Overseeing student well‑being, leadership, discipline, community service, athletics, outdoor education, technology, field trips, and key risk‑management practices.
• Partnering with Admissions on applicant review, student transitions, prospective family events, and enrolment‑related activities.
• Contributing to the school’s co‑curricular program and teaching one section.

The Ideal Candidate

The successful candidate will be an experienced school leader and inspiring educator who can balance strategic thinking with visible, hands‑on leadership. They will maintain a visible and engaged presence at school and at key St. Anne’s and Partnerhood events, strengthening relationships and demonstrating active support for the life of both schools. They will be an articulate and compelling ambassador for St. Anne’s, with the ability to build trust, navigate complex issues, manage change, and bring people together around a shared vision.

Qualifications and experience:

• A 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 a strong understanding of girls’ education and the opportunities of an all‑girls learning environment.
• A record of leading people and programs with integrity, empathy, sound judgment, and a commitment to continuous improvement.
• Exceptional communication, relationship‑building, conflict‑resolution, organizational, and problem‑solving skills.
• Experience in an independent or girls’ school environment is considered an asset.
• The role requires participation in occasional evening and weekend events, as well as some travel.
• The successful candidate will maintain the highest standards of professionalism, discretion, student safety, and confidentiality.

Please note that artificial intelligence (AI) tools will not be used in the screening or evaluation of applications; all materials will be reviewed directly by the Human Resources team.

The salary for this position is dependent on qualifications and experience and will range from $160,000 to 190,000.

We believe that diversity in our school fosters a rich, inclusive, and creative environment. We are actively engaged in building a more diverse school and encourage all qualified applicants to apply. By extension, we are committed to providing accommodations for persons with disabilities. If you require an accommodation through the recruitment process, please contact Human Resources at 905-727-2580.