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Jonathan Leard has extensive work experience in the non-profit sector, specifically with Big Brothers Big Sisters organizations. Starting in 2006, they worked as a Youth Care Worker for NSHCC until 2008. In 2008, they joined Big Brothers Big Sisters of the Annapolis Valley as a Mentoring Coordinator and later held roles as Program Manager and Executive Director. Jonathan then moved on to Big Brothers Big Sisters of Greater Halifax, where they served as a Mentoring Coordinator, Manager of Service Delivery, and most recently as Executive Director of Service Delivery. Currently, they are the National Director of Technology for Big Brothers Big Sisters of Canada, a role they started in 2022.

Jonathan Leard attended Holland College but did not complete a degree or specify a field of study. No information is given regarding the duration of their enrollment.