Assistant Head of School, Director of Upper School

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

We invite applications for a leadership opportunity e’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.

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.

• 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 e’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 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.

• 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…