Employment Opportunities
Job Postings
March 2026
PRINCIPAL
We are seeking a dynamic, faith-driven, and experienced Principal at Our Lady of the Wayside Catholic School and Chesterton Academy. Our Lady of the Wayside is a private Catholic classical education institution in Ontario, Canada, serving students from Kindergarten to Grade 12. The ideal candidate will be responsible for upholding the school’s mission, which integrates Catholic teachings, classical liberal arts education, and a supportive community environment. This role requires a visionary leader who can ensure academic excellence, foster spiritual development, and commitment to the school’s values for
the entire school.
The role is a full-time 5 days per week, with paid leave during Christmas, Easter and summer break.
View full principal job posting here
FINANCE & SYSTEMS ADMIN
Wayside is seeking a dynamic and experienced Finance & Systems Administrator with a strong background in bookkeeping to join our team. The successful candidate will be responsible for overseeing the school’s financial bookkeeping and maintaining various financial records and systems.
