Director, Philanthropy

at Greenwood College School, Toronto, Canada

Listed on EduAtlas: live school vacancies from schools’ own careers pages and public job services. Apply on careers.cais.ca.

Salary

CAD 115,000 to 130,000 a year

Closing date

7 December 2026

Start

January 2027

Contract

full time

First seen

30 October 2026, on a public job listing

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The advert

DIRECTOR, PHILANTHROPY Greenwood College School is seeking a Director, Philanthropy to help shape the next phase of our philanthropy as we step into the next 25 years of Greenwood. This is an active recruitment for a full-time position commencing in January 2027. About Greenwood Greenwood College School was founded to inspire students to venture further in order to prepare them for the challenges and experiences of life through a focus on character. A co-ed / gender inclusive independent day school for students in Grades 7 through 12, Greenwood embraces a student-focused education, inspiring its students to thrive now and in the future. Our goal is to be the best school in Canada for personalized learning and innovative teaching. With a strong sense of community and a focus on the whole person, experiential learning is a key part of a Greenwood education. Compensation & Terms The expected salary range for this position is $115,000-130,000. This is an ongoing contract position. Working Requirements Greenwood’s professional culture is highly collaborative. Accordingly, the successful candidate must demonstrate a willingness to collaborate with colleagues. All staff members participate in job-embedded professional development. Greenwood is a dynamic place to work, where creativity is encouraged and valued, and where fun and excellence merge together. Position Summary As Greenwood embarks on its 25th anniversary and looks ahead to future campaigns advancing our highest priorities, strategic planning, strong development operations, and close collaboration across the Advancement team are central to translating philanthropic ambition into lasting impact. The Director, Philanthropy will provide leadership for major, principal, and complex gift fundraising efforts, overseeing the planning and execution of major and comprehensive gift strategies to achieve annual and campaign revenue goals. Managing a select portfolio of top donors, they will foster a high-performing, donor-centered culture, ensuring that all fundraising activities are aligned with Greenwood’s mission, vision, values and long-term objectives. Working closely with Advancement colleagues, volunteers, and school staff, primary responsibilities include but are not limited to: Fundraising, Donor Engagement and Stewardship: Lead major gift, donor engagement, and campaign strategies to achieve an individual annual fundraising target of $500,000 to $750,000 per year. Develop and implement fundraising plans, cultivate and solicit major gifts, and ensure effective donor stewardship. Collaborate with the Executive Director, Advancement & Community Engagement, Senior Leadership Team, staff and volunteers to advance philanthropic priorities. Working with the Executive Director, Advancement & Community Engagement, develop strategies for and implement annual giving across all constituents. Provide oversight and input to the Annual Report, ensuring compelling storytelling, clear articulation of philanthro

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