Executive Director, Strategy

One of North America's foremost boys' schools, Upper Canada College provides transformational

learning experiences within an environment of teamwork, care, and mutual respect. Founded in

1829 with a commitment to public purpose, UCC is a progressive, high-performance school that

values learning, pluralism, service, community, and wellbeing. A UCC experience is about

celebrating differences, cherishing similarities, and giving voice to multiple perspectives –

inspiring each boy to be his best self and to make a lasting and positive impact on his world.

The only all-boys' International Baccalaureate Continuum World School in North America, UCC

enrolls over 1,280 students in Senior Kindergarten through Year 12, including boarding students

from around the world. Located in the heart of Toronto on 35 acres of green space, UCC is

dedicated to creating exceptional learning environments supported by expert faculty, cutting-

edge facilities, and wide-ranging co-curricular offerings. The College's graduates are highly

regarded by top universities worldwide, and alumni include leaders and innovators in politics,

finance, arts, athletics, media, and beyond.

Executive Director, Strategy

Reporting to the Principal, the Executive Director, Strategy (ED) will contribute as a member of

the Senior Leadership Team. The ED will collaborate with UCC's senior leaders to develop and

implement strategic initiatives, offering confidential advice and working with internal and

external subject-matter experts to provide strong analytical and facilitative support. The ED

will lead broad consultations, co-develop solutions, assess and refresh strategic elements in

support of evolving priorities, and embed principles of quality improvement into strategic

planning and execution across all UCC's endeavours. Further responsibilities include identifying

and building productive partnerships, incorporating data analysis, and guiding the selection,

sequencing, design, evaluation, resourcing, and execution of initiatives that will materially

shape UCC's future success.

With a degree, as well as expertise in project management and change management, the

Executive Director, Strategy will bring 10 years of progressive experience developing and

implementing strategy in an educational or related environment. Collaborative, creative, and

engaged by UCC's vision and mission, the ED will have compelling communication skills and a

proven ability to move easily between high-level strategy and detailed execution. A trusted

colleague, mentor, and guide, this leader will pair strong analytical skills with energy, good

humour, and an unmatched service ethic. Open-minded, adaptable, and sharing UCC's values of

learning, pluralism, service, community, and wellbeing, the Executive Director, Strategy will be

a connector, synthesizer, and organizational enabler, who mobilizes colleagues to advance

strategic goals and achieve meaningful change across multiple objectives.

UCC is an Equal Opportunity Employer and values diversity, encouraging applications from all qualified

individuals including women, Indigenous Peoples, persons with disabilities, 2SLGBTQIA+ and historically

marginalized persons. 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 candidates; however,

Canadian citizens and permanent residents will be given priority. All responses to Caldwell are 

confidential. For information on Caldwell's privacy policy, please see:

The appointment will be made as soon as possible. This full-time

position is based in Toronto (200 Lonsdale Road, Toronto, ON M4V 1W6). The language of work is

 English.The successful candidate will have educational qualifications and leadership experience

 appropriate to the role. Applications will be reviewed immediately upon receipt.