Executive Director, Development

Pickering College is more than a place to teach - it’s a vibrant community where educators grow, collaborate, and inspire. As Canada’s only Quaker-founded independent day and boarding school for JK to Grade 12, we provide a dynamic environment that empowers teachers to bring learning to life and make a lasting difference for students and the wider world.

Guided by our values of Simplicity, Peace, Integrity, Community, Equality, and Stewardship, our culture is built on purpose, respect, and collaboration. These principles shape not only the student experience but also the workplace setting, creating a supportive environment where educators thrive both personally and professionally.

Reporting to the Head of School, the Executive Director of Developmentwill drive the philanthropy initiatives to ensure that the vision for the future of Pickering Collegeis fulfilled. The Executive Director will lead a team of professionals in Development, Parent Relations, Alumni Relations, and Community Relations. The Executive Director manages all components of the strategic fundraising plans including major gifts, special events, donor stewardship, planned giving, and annual giving. The Executive Director is expected to reach or exceed targets established to increase the school’s endowment, fund capital projects as established by the campus master plan, and fund other projects as determined by the school’s leadership.

Given the dynamic and collaborative nature of our school environment, this role is on‑site, five days a week with some evening or weekend work as required.

• Be recognized as a passionate, strategic, articulate and sincere ambassador for the school to our internal and external constituents.
• Successfully lead all fundraising activities including capital campaigns developing a campaign plan, engaging senior level volunteers, building the infrastructure required to support the campaign and ensuring the campaign reaches or exceeds its goal.
• Provide leadership to identify, qualify, cultivate, solicit, and provide stewardship to major gift donors and top prospects in consultation and partnership with the department and other stakeholders, effectively building and executing a meaningful major gifts program and planned gifts program.
• Grow the prospect list and incorporate it into the major gift prospect tracking system.
• Complete and implement an integrated fundraising, parent, alumni and community relations plan, including engagement, cultivation and stewardship, that is aligned with the school’s strategic plan so that it immediately starts to advance the school’s relationship with its constituents, thus achieving increasing goals for annual, major and planned giving programs.
• Increase alumni and parent participation in school initiatives—such as giving, event attendance, and volunteerism—by setting annual engagement benchmarks and using data-driven insights to evaluate progress and refine strategies.
• Develop effective solicitation strategies for each constituent group and prospects to lead to positive long-term philanthropic relationships.
• Provide inspired direction in leading the Development Team, by offering coaching, guidance, professional development and supervision.
• Work with the Development staff on tracking each prospect, ensuring that each move through the donor journey process is done with effectiveness and efficiency.
• Identify, recruit, train, and lead volunteers, including meaningful and aligned engagement activities in support of fundraising.

Collaborate with the Communications Team to ensure that all development and engagement materials—such as donor proposals, event collateral, and stewardship pieces—are reviewed for brand consistency, tone, and alignment with institutional messaging, while content creation remains the responsibility of the Development team.

• Demonstrated relationship-building skills
• General business acumen and the ability to leverage key influencers to achieve goals.
• Work effectively with the Senior Leadership Team, Board and Corporation members
• Focused strategist, compelling speaker and excellent written communication skills.
• Ability to reach out to and engage alumni with a broad range of ages and diverse backgrounds.
• Ability to bring together, inspire and motivate a team of professionals.
• Strong organizational, time management and analytical skills.
• Ability to manage organizational change.
• Sound knowledge of how technology can best support integrated advancement strategies.
• Leverage personal past and existing Development staff relationships to develop a robust succession plan.

• Demonstrated success in leading a high achieving team including capital campaigns - from planning through to successful completion.
• Proven track record of success in securing major gifts at $100,000 level and above.
• Outstanding success in revenue generation and the drive to achieve results.
• At least 5 years Development experience with proven Development management experience.
• Ability to develop major gift cultivation and solicitation strategies, including writing custom proposals, negotiating gift terms and bringing solicitations to closure.
• Knowledge of Canada Revenue Agency guidelines pertaining to charitable giving and understanding of the implications for major and planned gifts.
• Knowledge of, and experience working with Raiser’s Edge NXT.
• Strategic thinker who can communicate and implement the school’s vision for growth.
• Strong commitment to Pickering College’s vision, mission and values.
• University degree and ongoing professional development in the fundraising field.

Pickering College provides a competitive compensation package, including a Health Benefits Plan and participation in our group RRSP.

The use of AI is not used during the recruitment process.

Pickering College is committed to building and sustaining a pluralistic community.We actively seek students, families, faculty, and staff of varied backgrounds and encourage them to share their unique gifts to cultivate a rich educational environment. We strive to create a learning environment that exposes students to the value and breadth of differences, informs their perspective, and prepares them to shape the world.

As a condition of employment, the successful candidate(s) must provide a current Vulnerable Sector Screening Police Report. Suitable accommodations are available for applicants with accessibility needs due to disability upon request.