Play a key role in the future of this iconic community foundation!

About Winnipeg Foundation

Winnipeg Foundation is For Good. Forever. We help people give back to our shared community by connecting generous donors with causes they care about For Good. We are an endowment-based public foundation, so gifts are pooled and invested, and the annual earnings are distributed back to the community Forever. Founded in 1921, we are proud to be Canada's first community foundation. Our vision is ‘a Winnipeg where community life flourishes for all.’

The Opportunity

Reporting to the Vice President, Community Generosity, the Director of Generosity will lead donor-facing units within Community Generosity, including Generosity Planning and Planned Giving. This role will oversee donor-facing programs, including professional advisor engagement, donor-advised funds, legacy circle, family generosity, corporate generosity, employee giving, next-generation generosity, fund establishment, donor acquisition, and onboarding, and strategic or transformational generosity. The successful incumbent will be a strategic, supportive, relationship-driven leader who can translate strategic objectives into coordinated operational plans and align work across teams to contribute to donor satisfaction, fundraising performance and overall engagement.

Compensation The salary range for this role is $115,000 to $150,000. The successful candidate will be placed in the salary range depending on experience and qualifications.

Key Responsibilities

- In collaboration with the VP Community Generosity, develop and implement the Foundation’s Donor engagement strategy in alignment with the Foundation’s mission and values.
- Translate strategic objectives, set cross-team priorities, allocate approved resources,



and establish operational practices to ensure smooth deliverables of Generosity Planning and Planned Giving.
- Oversee workplans, fundraising performance, donor satisfaction, process discipline, employee engagement, and team-alignment.
- Lead, coach, and develop Generosity Planning and Planned Giving teams. establishing transparent accountabilities, performance expectations, decision-making authority, and a collaborative, inclusive, improvement-focused culture.
- Provide strategic leadership to develop, maintain, and expand philanthropic relationships with donors, coaching managers to navigate complex donor goals and concerns with sensitivity.
- Manage a small portfolio of transformational donors, overseeing donor engagement activities, stewardship approaches to enhance long-term connection and alignment with policies, values, and community priorities.
- Responsible for the management of resources, regulatory compliance, budget, contracts, procurement, forecasting, and planning, including staffing needs.
- Build and integrate systems, processes, and procedures to achieve effective workflow, optimal fundraising performance, and seamless administration and reporting.

Selection Criteria

- Degree in Fundraising, Non-Profit Management, Business, or related field, or equivalent combination of education and experience.
- Certified Fund-Raising Executive (CFRE) designation or willingness to obtain.




- 10+ years’ progressive experience in fundraising, donor engagement, generosity planning, planned giving or related field.
- 5+ years of people-leadership experience, including leading fundraisers or donor-facing professionals.
- Experience managing individual donor relationships and a donor portfolio.
- Proven ability to lead and manage staff, including developing teams and overseeing organizational priorities.
- Seasoned team leader and coach, focused on fostering a positive culture, employee engagement, and on-going learning.
- Operational and change leader with the ability to build and execute departmental plans, manage a diverse portfolio and multiple projects and integrate processes with cross-functional teams.
- Experience with portfolio and project management, building management frameworks, and leading cross-functional initiatives.
- Experience implementing or integrating a CRM system, leading change, and configuring business process and workflows.
- Excellent strategic, critical thinking, analytical and decision-making skills, coupled with a relationship-driven approach.
- MFA-P, CSPG, and/or TEP designations are assets.

To apply, please submit a resume and cover letter detailing how you meet the position requirements. If your background looks different from described above, in your cover letter, tell us why you would be a good fit!

Applicants who do not fully satisfy all the essential requirements are nonetheless encouraged to submit their applications for consideration regarding this position. We firmly believe in the potential for diverse perspectives, skills, and experience to enrich our team and contribute to the Foundation’s overall success.

📌 Director of Generosity - Winnipeg Foundation
🏢 Harris Leadership Strategies
📍 Winnipeg