Assistant Head of School, Director of Upper School

Assistant Head of School, Director of Upper School

Posted: 9/30/2026 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.

Back

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.

Empowering girls to be courageous learners and compassionate citizens who live and lead with wisdom.

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