Lead major gift fundraising at Greenwood College School, using donor engagement and strategic planning to advance philanthropic priorities. This is a full time position commencing January 2027.

The Director, Philanthropy will lead major, principal, and complex gift efforts for Greenwood’s next 25 years. This senior fundraising leader will oversee campaign strategies, donor stewardship, advancement operations, and revenue performance. Collaboration with Advancement colleagues, volunteers, senior leaders, and school staff is central to the position.

Key Responsibilities:
Lead major gift, donor engagement, and campaign strategies
Cultivate, solicit, and steward major gifts
Oversee donor portfolios and solicitation planning
Use advancement data to forecast revenue and guide decisions




Prepare donor reports, agreements, and briefing notes

Requirements:
Seven or more years of progressive fundraising experience
High-level fundraising or principal gifts experience
Experience managing portfolios exceeding $500,000 annually
Proven success closing significant gifts through direct solicitation
Solid communication, presentation, and relationship-building skills

Bring strategic philanthropy, principal gift fundraising, and donor stewardship expertise to Greenwood College School’s Advancement team.
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📌 Director Philanthropy Major Gifts Toronto
🏢 CAIS
📍 Toronto