Associate Director, Stewardship

WILLIAM OSLER HEALTH SYSTEM FOUNDATION

Job Posting

JOB TITLE: Associate Director, Stewardship (Full-Time, Permanent)

REPORTING TO: Vice President, Philanthropy

LOCATION: Peel Memorial Centre for Integrated Health & Wellness, with travel to Brampton Civic and Etobicoke General Hospitals

WILLIAM OSLER HEALTH SYSTEM FOUNDATION:

Osler Foundation is the fundraising arm of William Osler Health System (Osler). Osler serves 1.3 million people in Brampton, Caledon, North Mississauga, Etobicoke, and the surrounding region. This is one of the fastest growing and most ethnically diverse regions of Canada. Osler Foundation builds and fosters relationships in our hospitals and the community to raise funds to support the clinical priorities at Brampton Civic Hospital and Etobicoke General Hospital, Osler’s two acute-care sites, and Peel Memorial Centre for Integrated Health and Wellness.

As part of the Osler System family, we are committed to providing a fulfilling work environment that inspires our staff to learn, innovate, and grow. Year after year, Osler is proud to be recognized as one of Greater Toronto’s Top Employers and Canada’s Best Diversity Employers. Osler Foundation is committed to supporting our employees through flexible work arrangements, professional development, and a commitment to creating an environment of inclusiveness and belonging.

POSITION SUMMARY:

Osler Foundation is entering a defining moment in its history through a transformational Capital Campaign that will shape the future of health care in our community. Reporting to the Vice President, Philanthropy, the Associate Director, Stewardship will play a pivotal leadership role within a high-performing fundraising team during a period of significant growth and strategic opportunity. This role provides direct supervision to a Philanthropy Officer and is accountable for advancing a best-in-class donor experience function that strengthens stewardship, recognition, and long-term donor engagement.

This position offers the opportunity to design and lead a comprehensive donor experience and stewardship strategy that elevates donor recognition, deepens engagement, and clearly demonstrates philanthropic impact. The successful candidate will bring a strategic, innovative, and donor-centred approach to building and enhancing engagement programs, leveraging sector best practices and emerging trends in philanthropy to position Osler Foundation as a leader in donor stewardship, retention, and growth.

In close collaboration with colleagues across the Foundation and William Osler Health System, the Associate Director, Stewardship will lead the development and execution of tailored stewardship strategies for major gift donors while overseeing the delivery of integrated cultivation, stewardship, and recognition initiatives that support campaign priorities and broader fundraising objectives.

This role requires a sophisticated understanding of donor-centred philanthropy, exceptional strategic and operational judgement, and the ability to translate vision into high-quality execution. Strong leadership, meticulous attention to detail, and the ability to navigate complexity, anticipate needs, and drive solutions will be essential to success.

RESPONSIBILITIES (including but not limited to):

Strategic Stewardship & Donor Experience (35%)

• Develop and lead a comprehensive donor relations, recognition, and stewardship program that enhances the donor experience across all giving segments and strengthens donor engagement, retention, and long-term philanthropic support.
• Design and implement innovative and customized stewardship strategies that meaningfully connect donors to the impact of their philanthropy and inspire continued support for the Foundation’s mission and strategic priorities.
• Develop tailored stewardship and engagement plans for major gift donors.
• Champion a donor-centred culture by serving as an advocate for the donor perspective across stewardship, communications, engagement, and recognition activities.
• Oversee donor recognition initiatives, including naming recognition and plaque processes, ensuring commitments are executed accurately, thoughtfully, and in alignment with donor agreements and Foundation standards.
• Stay informed of emerging trends, best practices, and innovations in donor relations, stewardship, and philanthropy through ongoing professional development and participation in relevant networks and associations.

Events, Engagement & Communications (35%)

• Collaborate with the Foundation’s Fundraising Communications Specialist and William Osler Health System to create compelling donor communications and stewardship collateral, including impact reports, naming opportunity proposals, recognition materials, presentations, and donor correspondence.
• Design and execute meaningful donor cultivation, stewardship, and recognition initiatives — including events, digital engagement opportunities, and customized experiences — that strengthen relationships with donors, volunteers, and prospective supporters.
• Lead the planning, coordination, and execution of donor cultivation and stewardship events, ensuring exceptional experiences and seamless logistics.
• Support donor and volunteer engagement strategies that increase awareness, deepen connection to the Foundation’s mission, and advance fundraising priorities, including the Foundation’s future campaign initiatives.
• Represent the Foundation at community events, donor functions, and organizational activities as required.

Leadership & Team Development (20%)

• Provide leadership, mentorship, and day-to-day supervision to the Philanthropy Officer, fostering professional growth, collaboration, accountability, and a strong donor-centred approach to stewardship and donor relations activities.
• Contribute to a collaborative, high-performing team environment while demonstrating initiative, sound judgment, adaptability, and the ability to manage multiple priorities in a dynamic and fast-paced setting.

Operations, Collaboration & Administration (10%)

• Maintain accurate and timely donor records, stewardship activities, recognition tracking, and engagement documentation within Raiser’s Edge to support relationship management, reporting, and operational excellence.
• Foster strong collaborative relationships across Foundation and hospital departments to support integrated fundraising, stewardship, and donor engagement strategies.
• Demonstrate a commitment to the mission, vision, and values of William Osler Health System and Osler Foundation, including an appreciation for serving one of Canada’s most culturally diverse communities.
• Other duties as assigned.

QUALIFICATIONS:

• University degree in fundraising management, marketing, communications, business administration, or a related field, or an equivalent combination of education and experience.
• A recognized fundraising designation (CFRE) or related professional certification is considered an asset.
• Minimum five (5) years of progressive experience in donor relations, stewardship, donor experience, or major gifts fundraising, including designing and delivering innovative donor engagement and recognition programs.
• Demonstrated experience working in a major gifts and/or capital campaign fundraising environment; experience within health care philanthropy or a complex not-for-profit organization is preferred.
• Proven ability to develop and implement strategic donor stewardship, recognition, and engagement initiatives that strengthen donor relationships and inspire continued philanthropic support.
• Experience managing donor recognition programs, stewardship reporting, naming opportunities, and fulfillment of donor agreement commitments.

WHAT YOU WILL ENJOY:

• A comprehensive benefits package including a defined-benefit pension plan (HOOPP), outstanding health/dental benefits, and a generous vacation allowance.
• An expected starting salary range of $95,000 - $110,000.
• The Foundation is working under a hybrid model of work from home and in office on a weekly basis.
• State-of-the-art accessible facility located close to major highways in Brampton, Ontario
• A dynamic and professional office setting in a hospital environment.
• A highly collaborative team environment with the opportunity to participate in first-in-class fundraising events.

APPLICATION INSTRUCTIONS:

Please submit a PDF of your cover letter and resume addressed to Jacqueline Rodgers, President’s Office & Board Liaison

• Email: jacqueline.rodgers@williamoslerhs.ca
• Subject Line: Associate Director, Stewardship
• Deadline: Friday August 14, 2026

We thank all candidates for their interest. Only those selected for an interview will be contacted. No telephone or walk-in inquiries, please. Please note that we will be conducting interviews with chosen candidates prior to the closing date.

All applications are considered confidential.

Osler values inclusivity and diversity in the workplace. We welcome and encourage applicants from diverse backgrounds. We are committed to providing accessible employment practices that comply with the Accessibility for Ontarians with Disabilities Act (AODA). If you require accommodation at any stage of the recruitment process, please notify us through your application.

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