Head of Upper School

At the forefront of women’s education for more than 130 years, Havergal College is a leading independent day and boarding school for girls in Toronto, grounded in the principles of a liberal arts education and committed to preparing young women to make a difference. Situated on a beautiful 22-acre campus, Havergal serves 1,080 students from Junior Kindergarten to Grade 12, employs approximately 250 faculty and staff, and has a global network of more than 9,500 alumni. Guided by the values of Integrity, Inquiry, Compassion, and Courage, the College offers a rigorous curriculum built on the pillars of academics and wellbeing. Through outstanding curricular and co-curricular programs, Havergal fosters self-confidence, leadership, critical thinking, inquiry, and teamwork, empowering students to shape their own education and navigate a rapidly changing world.

Reporting to the Deputy Principal and serving on the Senior Leadership Team, the Head of Upper School provides strategic and operational leadership for Grades 7–12, ensuring an exceptional student experience aligned with Havergal’s mission, values, vision, and strategic plan. Working closely with the Dean of Academics, Head of Junior School, and academic and operational colleagues, this leader will guide the Upper School’s academic, wellbeing, co-curricular, and operational programs; foster student success and belonging; and build strong relationships with families and the broader school community. The Head of Upper School will build relationships, mentor, coach, and develop faculty and school leaders, and foster a collaborative, accountable culture of continuous improvement.

The successful candidate will hold an advanced graduate degree, preferably in Education, and at least 10 years of educational leadership experience in a Grade 7–12 environment, together with Ontario College of Teachers certification or the capacity to become certified. Principal’s Qualifications or equivalent leadership preparation are preferred. With deep knowledge of adolescent development, student wellbeing, curriculum implementation, school operations, and girls’ education, this leader will demonstrate exceptional people-management skills: setting clear expectations, giving constructive feedback, developing high-performing teams, identifying emerging leaders, and navigating change with managerial courage. Collaborative, inclusive, and results-oriented, the Head of Upper School will inspire excellence in teaching and learning while helping every student and employee thrive.

Havergal believes that great schools are made up of great people, and is committed to building a diverse workforce and an inclusive workplace. The College encourages applications from all qualified candidates with a diverse range of experiences and perspectives, including women, BIPOC (Black, Indigenous and People of Colour) peoples, and persons with disabilities. Driven by its core values of inquiry, compassion, integrity, and courage, Havergal welcomes applicants inspired by its mission to prepare young women to make a difference. The College is committed to equal opportunity and a barrier-free environment, respects the requirements of the Accessibility for Ontarians with Disabilities Act, 2005, and its associated Regulations, and makes every reasonable effort to accommodate accessibility needs. Accommodations are available upon request throughout the recruitment and selection process.

The next Head of Upper School will join Havergal in July 2027. Applications will be reviewed upon receipt. While the application deadline is December 18, 2026, the posting will remain active until a successful candidate has been selected. All responses to Caldwell Partners are confidential. Please indicate your interest in Project 261036 at https://caldwell.thriveapp.ly/job/1340. Caldwell Partners’ Privacy Policy is available here. Havergal College is located at 1451 Avenue Rd, North York, ON M5N 2H9.