Director, Philanthropy

CAIS; Toronto; On-site; CAD 115,000 - 130,000; Full time

Job summary

Greenwood College School in Toronto is seeking a Director, Philanthropy to help shape the next 25 years of Greenwood. You will lead major gift fundraising and campaign activity, guiding strategy and donor engagement to maximize impact.

Working with the Advancement team, volunteers and school leadership, you will manage portfolios, develop plans, and ensure compelling storytelling and accurate donor recognition.

Qualifications

• Seven (7)+ years of progressive fundraising experience with focus on high-level gifts and campaigns.
• Experience managing high-value donor portfolios with defined annual revenue expectations over $500k.
• Experience coaching advancement staff with clear performance metrics.
• Ability to work with senior leaders on high-stakes solicitations.
• Experience in campaign or growth-focused fundraising settings.

Responsibilities

• Lead major gift, donor engagement, and campaign strategies to achieve annual fundraising targets of $500,000 to $750,000 per year.
• Develop fundraising plans, cultivate and solicit major gifts, and ensure donor stewardship.
• Collaborate with Executive Director, Advancement & Community Engagement, SLT, staff and volunteers to advance priorities.
• Work with leadership to implement annual giving across constituents.
• Provide oversight for Annual Report and donor recognition coordination.

Skills

Fundraising strategy

Donor engagement

Major gifts

Portfolio management

Leadership / coaching

Stakeholder management

CRM systems

Data analytics

Education

Experience in education sector

Tools

Raiser’s Edge

Google suite

Canva

CharityCan

Job description

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 philanthropic impact and coordination with colleagues to confirm accurate donor recognition.

Portfolio Strategy and Performance

• Oversee donor portfolios, prospect management, solicitation planning, and fundraising performance.
• Use advancement data and analytics to monitor progress, forecast revenue, and inform strategic decisions.
• Ensure compliance with fundraising best practices, ethical standards, and institutional policies.

Strategic Planning and Collaboration

• Align fundraising initiatives with school priorities, campaign objectives, and philanthropic trends.
• Collaborate with Executive Director, Advancement & Community Engagement and Principal, Head of School, to identify funding opportunities and advance fundraising strategies.
• Provide guidance on fundraising policies and governance, represent Advancement and Alumni on institutional initiatives, and act on behalf of the Director as required.

Advancement Operations and Administration

• Foster a collaborative, accountable, and donor-centred work environment.
• Prepare reports as required for the Advancement Committee and Board and Foundation Board as required
• Manage all constituent records and ensure all data is recorded in a timely fashion in Raiser’s Edge or other similar Advancement database.
• Prepare donor reports, gift agreements, briefing notes, and any other materials and documents that assist the Advancement team with donor cultivation, stewardship, or solicitation where applicable.
• Other Advancement duties as required to support the functioning of this department/the school.
• Maintain strict confidentiality in all matters.

Committee

s: Parent/Guardian; event committees as needed

The Director, Philanthropy will report to the Executive Director, Advancement & Community Engagement, and will support all aspects of the Advancement & Community Engagement department in an independent and highly professional manner.

Qualifications and Personal Characteristics

• Seven (7)+ years of progressive fundraising experience, with a demonstrated focus on high-level fundraising and/or principal gifts
• Experience managing high-value donor portfolios with defined annual revenue expectations in excess of $500,000
• Experience managing and coaching advancement staff with clear performance expectations and revenue metrics
• Ability to work effectively with senior leaders to prepare and execute high‑stakes solicitations
• Experience working in campaign or growth‑focused fundraising settings
• Proven success initiating and closing significant gifts through direct, proactive solicitation
• Strong relationship‑building skills with donors, senior leaders, and staff
• Demonstrated ability to use advancement databases, CRM systems, and data to inform strategy and decision‑making
• Technical skills including familiarity with the Google suite of applications for work, Canva, CharityCan, and other applications
• Excellent communication, presentation, and interpersonal skills
• Knowledge of the independent school community and/or higher education sector is preferred
• Action‑oriented
• Ability to set and achieve personal and team goals and objectives
• Positive, outgoing personality and willingness to take risks and learn new skills
• Creative problem solver with a solutions‑oriented approach
• Ability to work before/after hours on occasion for Advancement/Alumni and school events
• Appreciation of a small school/small office environment
• Understanding of Greenwood’s mission and values

Greenwood’s Commitment to Pluralism and Accessibility

Greenwood is committed to creating and sustaining a diverse, equitable and inclusive environment for staff, students and families. We aim to embrace individuals whose differences include, but are not limited to: age, ancestry, citizenship, colour, creed, disability, ethnic origin, family status, gender expression, gender identity, marital status, place of origin, race, and sexual orientation. Greenwood is an equal opportunity employer and welcomes applications from all qualified individuals. We embrace pluralism – an ethic of respect that values human diversity. We strive to create a workplace where everyone feels valued, respected and empowered to contribute authentically.

Accommodations are available on request for candidates with disabilities at all stages of the selection process.