Head, Upper School | Upper Canada College (UCC)

Upper Canada College (UCC) is recognized globally as one of North America’s foremost boys’ schools. Educating tomorrow’s leaders since 1829, UCC is an International Baccalaureate (IB) Continuum World School for day and boarding students from senior kindergarten through university entrance. Modern and forward-thinking, UCC provides transformational learning experiences that foster the development of head, heart, and humanity, and inspire each boy to make a lasting and positive impact on his world. UCC delivers a rigorous academic program supported by accomplished faculty and staff, exceptional co-curricular programming, and state-of-the-art facilities. 

UCC offers congratulations to Jeff Aitken, the current Head, Upper School, who will take up the post of Principal, St. Michaels University School, in the summer of 2025. The next Head of UCC’s Upper School will build on success to lead excellence in teaching and learning and inspire a culture that exemplifies UCC’s values of learning, pluralism, service, community, and wellbeing. This role also presents the opportunity to co-lead the implementation of two graduation pathways being introduced in addition to the IB Diploma Programme Pathway: the IB Diploma Programme Courses Pathway, and the IB Diploma Programme  Systems Transformation Pathway (a Programme being offered by only four schools globally). 

Being the Head of UCC’s Upper School is akin to running your own complex, well-resourced school with over 800 students (in grades 8 through 12) and over 100 employees. This role oversees a broad range of functions including faculty recruitment and development, program delivery, budgeting, boarding, university counselling, and parent relations. At the same time, you will work closely and collaboratively with the Principal and other members of UCC’s senior leadership team to advance the strategic goals of the entire College and its 1,260 students. Among its strategic goals is UCC’s ambition to become more diverse and inclusive. This is supported by a recognition that no learning community is whole without the inclusion and amplification of multiple voices; UCC is committed to fostering belonging, striving for justice and peace among all people, and addressing systemic and structural forms of oppression.

You are an academic leader in a progressive, high-performance school. Your educational leadership experience in academic, co-curricular, and community service programs will enable you to support the learning and social needs of UCC’s Upper School students. An insightful strategist, inspiring educator, and collegial leader, you will attract and engage with faculty and staff who are energized by attempting fresh approaches, connecting with students, serving the community, and delivering all-round excellence in teaching and mentorship. You are a life-long learner and a nuanced, non-linear thinker with experience in change management. Internationally minded and committed to shared guardianship of the planet, you are compassionate, culturally competent, and prepared to have brave conversations about identity and marginalization. If you are ready to grow as a leader, this is a role with real impact: an opportunity to ensure that each Upper School boy is supported and readied on every step of his path toward graduation, post-secondary, and the life beyond. 

UCC is an Equal Opportunity Employer and values diversity, encouraging applications from all qualified individuals. UCC embraces pluralism – celebrating differences, cherishing similarities, and giving voice to multiple perspectives. If you are contacted regarding a UCC opportunity, please advise if you require any accommodations. UCC encourages applications from all qualified applicants; however, Canadian citizens and permanent residents will be given priority.

The Head of the Upper School will take up the position in the summer of 2025, for a five-year, renewable term. This is a full-time position, based in Toronto (200 Lonsdale Road, Toronto, ON  M4V 2X8). The language of work is English. The successful candidate will be a qualified teacher with post-graduate qualifications and leadership experience appropriate to the role. Applications will be reviewed immediately upon receipt. All responses to Caldwell Partners are confidential. Please indicate your interest in Project 240726 at https://caldwell.thriveapp.ly/job/1162 or email hring@caldwell.com.