Head of School
Content + Source + Freshness • 13 Dec 2025 • 95% confidence
Offer value
Exceptional opportunity due to competitive salary, the prestige of the school, and the potential to influence educational practices.
- Competitive salary: $326,000/year
- Leadership role with significant influence on educational practices.
- Prestigious position at a top independent school
- Requires strong educational leadership experience.
Pros
- High salary ($326,000/year) reflective of the Head of School position.
- Significant impact on educational direction and student development.
- Leadership role in a well-established school with a strong reputation.
Cons
- High expectations and challenges associated with leading a large school.
- Potential for long hours and high levels of responsibility.
- Requires extensive experience in educational leadership.
Who it's for
Executive / Leadership • On-site leadership role
Good fit
- Seasoned educational leaders
- Professionals seeking to influence education positively
- Individuals with a passion for community engagement
Not recommended for
- Entry-level educators or new leaders
- Those seeking a low-responsibility role
- Candidates without a background in educational environments
Motivation fit
Key skills
About the job
Collingwood is one of Canada’s largest independent day schools, enrolling 1,260 students across two campuses: Wentworth (Junior School, JK–7) and Morven (Senior School, Grades 8–12). A Collingwood education provides a personalized, real-world approach to education, building strong academic foundations in literacy and numeracy. We foster curiosity and independence, challenging students to apply skills beyond knowledge. Our diverse co-curricular program in Academics, Arts, Athletics, and Service allows students to explore their passions and discover their unique purpose in the world. Collingwood graduates are sought after by top universities and carry forward a lifelong sense of belonging and pride.
The school enjoys financial health, engaged governance, and a clear strategic outlook supported by philanthropy and robust reserves. It continues to innovate in areas such as AI integration, experiential and outdoor education informed by Indigenous partnerships, and a unique 2-5-1 trimester model at the senior school positioning Collingwood at the forefront of independent schooling in Canada.
The Board of Governors now seeks an exceptional and community-minded leader to succeed Lisa Evans, who will step down as Head of School in summer 2026 after 32 years of dedicated service, including 17 years as Head of Morven Campus and 8 as Head of School.
This is a rare and rewarding opportunity for an accomplished educational leader to shape the future of Collingwood. The next Head of School is expected to start in July 2027 at the latest, and will steward Collingwood’s traditions while advancing a forward-looking agenda that engages its present and inspires its future. Building on a legacy of academic excellence, innovation, student wellbeing, and holistic education, the Head of School will join a passionate community and together build a shared vision for Collingwood’s next chapter.
The ideal candidate will be an accomplished and inspiring educational leader with strategic vision, a deep understanding of independent schools, and proven experience guiding complex organizations through growth and change. They will bring excellence in teaching and learning, strong governance and financial acumen, and experience in fundraising and long-term capital projects. Authentic and courageous, they will build trust and cohesion across diverse communities while leading with empathy, diplomacy, and integrity. Committed to student wellbeing, faculty development, and Collingwood’s values, the next Head will lead with clarity, collaboration, and purpose.
At Collingwood School, we are grateful to live, work and learn on the unceded traditional territories of the Skwxwú7mesh (Squamish), S?lilw?ta? (Tsleil-Waututh), and xwm?θkw?y??m (Musqueam) Nations. We are committed to acknowledging, respecting, and celebrating the land, people and spirit that spans our two campuses, as we aim to cultivate meaningful and long-lasting relationships with Indigenous communities.
To download the detailed candidate brochure for this role, including details of how to apply, please click https://plusportal.perrettlaver.com/VacancyDetail/edace8c4-4ad1-7ba4-5221-3a1d80a6bfbb.
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