Director of Philanthropy, Stewardship & Engagement - W1381

Summit Search Group has been retained by Siloam Mission on the recruitment of a Director of Philanthropy, Stewardship & Engagement. Located at 300 Princess Street in the heart of downtown Winnipeg, Siloam Mission has been a cornerstone of the community since 1961, providing comprehensive support to people experiencing homelessness and poverty through meals, shelter, clothing, crisis services, and long-term programming. The organization serves approximately 1,600 meals daily, engages more than 900 volunteers, and is driven by a mission to address and ultimately end chronic homelessness in Winnipeg.

Siloam Mission operates with a genuine belief that every person deserves dignity, community, and support. It is a place where the work is tangible, the impact is immediate, and the people behind the mission bring remarkable commitment to everything they do. For the right candidate, Siloam offers something few workplaces can: the opportunity to see, in real and human terms, the difference your work makes every single day.

The Opportunity

Reporting to the Chief Executive Officer, the Director of Philanthropy, Stewardship & Engagement is a senior leadership role with dual accountability: personally generating revenue through a portfolio of major gift relationships, and providing strategic oversight of a multidisciplinary department of approximately 15 people spanning fundraising, donor stewardship, communications, and volunteer services. This role calls for an experienced philanthropy leader who is equally at home closing a major gift and building the systems, culture, and team capability that sustain long-term fundraising growth.

This is a meaningful moment for Siloam Mission’s development function. The team has been strengthened through a period of interim leadership, with important progress made on stewardship practices, donor impact reporting, and overall team development. The incoming Director will inherit a department on an upward trajectory and will be expected to lead it into its next phase: driving growth in planned giving, expanding the donor base to younger generations, reactivating a historically successful schools outreach program, and modeling for the team what excellent major gift fundraising looks like in practice. The role also calls for a confident public presence, as the Director serves as a key spokesperson for Siloam Mission alongside and on behalf of the CEO.

Key Responsibilities

• Lead and oversee Siloam Mission’s fundraising, donor stewardship, communications, and volunteer services functions, collaborating with the senior leadership team and a multidisciplinary department of approximately 15 to achieve an annual fundraising goal and ensure the organization’s long-term financial sustainability.
• Personally maintain a portfolio of major gift prospects, cultivating and soliciting relationships through direct engagement, and support the CEO in managing a short list of transformational gift prospects with the potential to make a significant impact on the organization’s mission.
• Develop and execute a comprehensive, multi-channel fundraising strategy spanning individual giving, major and planned gifts, corporate partnerships, grants, monthly giving, and third-party fundraising, with particular focus on unlocking growth in planned giving and building the next generation of Siloam Mission supporters.
• Champion and model a culture of outstanding donor stewardship, overseeing the development of a Donor Journey that supports acquisition, retention, recognition, and long-term engagement, and ensuring donor impact reporting and charitable receipting meet the highest standards of accuracy, timeliness, and AFP and CRA compliance.
• Lead, coach, and develop a department team through a period of strategic growth and change, establishing clear expectations, fostering accountability and collaboration, supporting professional development, and building an aligned, high-performing culture across fundraising, stewardship, communications, and volunteer services.
• Represent Siloam Mission professionally and credibly across the community, including media engagements and public events; be genuinely present and visible within the organization’s operations; and prepare strategic reports, financial updates, and departmental forecasts for the CEO and other stakeholders.

Qualifications

• Post-secondary education in Fundraising, Nonprofit Management, Business Administration, Communications, or a related field; a Certified Fundraising Executive (CFRE) designation is considered a strong asset.
• A minimum of 5 years of progressive non-profit sector experience, including at least 5 years in a senior leadership role with direct accountability for both team performance and personal fundraising results; a track record of meeting or exceeding revenue targets is essential.
• Demonstrated personal success in major gift solicitation, with a proven track record of identifying, cultivating, and closing significant gifts; a working network of existing relationships within the Winnipeg philanthropic community is a meaningful asset.
• Breadth across the full fundraising spectrum, including major gifts, planned giving, annual and monthly giving, corporate partnerships, and grants, paired with the strategic thinking and analytical capability to turn data and trends into informed fundraising decisions.
• A results-driven, coaching leadership style with genuine comfort leading through change, building team capability, mentoring staff, and setting clear expectations; the ability to model the fundraising behaviours expected of the team is a core requirement of the role.
• Strong public presence and communication skills, with comfort engaging media, donors, and community partners across diverse settings; experience with DonorPerfect or similar CRM platforms; and a valid Class 5F driver’s licence with a clean abstract.

For more information or to submit your resume, please reach out to Matt Erhard at Summit Search Group, [email protected].

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