Head of Senior School

(Full-time, permanent position, commencing summer 2026)

Trinity College School (TCS) is a leading boarding and day school for approximately 600 students from Grades 5-12. The School is situated on a beautiful 100-acre campus in Port Hope, Ontario, one hour’s drive east of Toronto. Founded in 1865, the School places a balanced emphasis on academics, service learning, athletics and the arts – as both a long-held TCS tradition and a thoughtful approach to a 21st-century education. 

TCS is seeking its next Head of Senior School. Reporting to the Head of Trinity College School, the Head of Senior School is a key member of the senior leadership team and a trusted steward of the School’s mission. An experienced and collaborative educational leader, the successful candidate will bring a proven track record in independent school leadership, strong personal skills, and the ability to connect across a diverse school community.

The Head of Senior School assumes responsibility for the academic, student life, and student support functions of the Senior School (Grades 9-12). Working in partnership with three Assistant Heads — Academics, Student Life, and Student Support — who report directly to this role, the Head of Senior School provides coordinated leadership across all aspects of the student experience. They will collaborate closely with the Head of School, fellow senior leaders, faculty, staff, students, and parents.

In addition to cultivating meaningful relationships, the Head of Senior School will champion a rigorous and engaging academic program, uphold professional norms, and model the high standards expected of a world-class learning community. They will inspire excellence in teaching and learning, encourage thoughtful reflection and continuous growth among faculty, and ensure that students are supported and challenged to develop habits of the heart and mind for a life of purpose and service.

The ideal candidate places students’ interests and wellbeing at the forefront of all decisions. They demonstrate an unwavering commitment to fostering belonging, compassion, agency, and a healthy school culture. Highly engaged in all aspects of school life, the Head of Senior School serves as a visible leader, role model, and mentor; contributes to strategic planning and implementation; and ensures a safe, welcoming, and inclusive learning environment.

KEY RESPONSIBILITIES:

• Champion the holistic development of every student.
• Provide inspirational leadership to faculty, ensuring the delivery of exceptional curricular and co-curricular programs.
• Continuously improve teaching and learning by reviewing, refining, and advancing pedagogical approaches and instructional practices.
• Oversee faculty recruitment, supervision, and ongoing professional growth, fostering a culture of shared purpose and continuous improvement within the Senior School.
• Work collaboratively with the Admissions Office to support strategic and effective enrolment management.
• Partner with the Philanthropy, Alumni & Archives Office on initiatives that enhance the Senior School experience.
• Oversee budget planning and resource management to ensure responsible stewardship.
• Foster a culture of professionalism, accountability, and continuous growth among faculty and staff.
• Ensure alignment with the School’s mission, strategic priorities, and values, including the habits of the heart and mind.

QUALIFICATIONS: 

• Bachelor’s degree in Education; master’s degree. Member of Ontario College of Teachers in good standing (or equivalent).
• 8+ years of progressive leadership experience, ideally within an independent school setting (boarding experience an asset).
• Demonstrated experience working with adolescents, faculty, staff, and parents in a complex school environment.
• Strong understanding of best practices in pedagogy and student wellbeing.
• Familiarity with contemporary educational research and trends.
• Knowledge of Ontario Ministry of Education requirements and independent school accreditation standards, including CAIS.

SKILLS & ATTRIBUTES: 

• Proven leadership and team-building abilities.
• Excellent communication skills — active listening, clear writing, and effective speaking.
• Technologically confident and adaptable.
• Highly organized, self-directed, and able to juggle multiple priorities.
• Strong interpersonal skills, with the ability to work professionally and confidentially with all members of the school community.
• Demonstrated cultural competence, empathy, and sensitivity.
• High integrity, sound judgment, and a strong work ethic.
• Commitment to equity, diversity, inclusion, and a sense of belonging for all students and staff.

TO APPLY: 

Interested candidates are invited to submit a cover letter and résumé outlining their qualifications and vision for Senior School leadership. Applications are due no later than January 12, 2026. Consideration of candidates will begin immediately, and the new Head of Senior School will take office in the summer of 2026. Applications may be directed in confidence to: Head of Trinity College School, Stuart Grainger, c/o Jennifer Dunbar James at jdunbarjames@tcs.on.ca.

To learn more about Trinity College School, please visit www.tcs.on.ca. 

Trinity College School thanks all applicants for their interest, but can acknowledge only those selected for an interview.

TCS is an equal opportunity employer. TCS is committed to providing accommodations for persons with disabilities. The School will provide support in its recruitment processes to applicants with disabilities, including accommodation that takes into account an applicant’s accessibility needs. 

We celebrate the diversity of our school community, including differences in race, colour, religion, national or ethnic origin, gender, sexual orientation, and gender identity. We welcome candidates representing such diversity.

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