Vice President, Generosity

United Way Winnipeg (UWW), together with its donors, volunteers, and partners, exists to unite Winnipeggers from all walks of life around a shared purpose: making Winnipeg a better place for everyone. For more than six decades, United Way Winnipeg has inspired collective action, convened diverse voices, and invested in local solutions that address the root causes of poverty, inequity, and social exclusion.
As one of the largest and most trusted charities in Manitoba, United Way Winnipeg plays a critical leadership role in Winnipeg's social impact landscape. With a long history of community generosity and volunteer leadership, United Way Winnipeg brings individuals, workplaces, businesses, and community partners together to create meaningful and lasting impact.
United Way Winnipeg is a volunteer-led organization, guided by a strong partnership between volunteers and staff that is foundational to its structure and success. Supported by committed and passionate employees and thousands of volunteers across the city, the organization is committed to building a culture of generosity that engages people, strengthens relationships, and inspires collective action. As the philanthropic landscape continues to evolve, United Way Winnipeg is focused on creating new opportunities for participation, deepening donor relationships, and ensuring its legacy of generosity continues for future generations.
The OpportunityUnited Way Winnipeg is seeking a strategic, creative, and values-driven Vice-President, Generosity – an inspirational and collaborative leader who will champion a renewed approach to philanthropy, strengthen community engagement, and inspire Winnipeggers to see themselves as part of a collective movement for change.
Reporting to the President & CEO and serving as a member of the Strategic Leadership Team, the Vice-President, Generosity will provide strategic leadership for United Way Winnipeg's fundraising efforts, including its annual Campaign for the Community Fund, major donor philanthropy, volunteer engagement, and donor stewardship. The Vice-President will be responsible for strengthening donor participation and retention, advancing sustainable revenue growth, and creatively designing the entire giving experience, from the first point of engagement through to ongoing stewardship.
This is an exciting opportunity to shape the future of generosity in a city with a remarkable history of philanthropy and community leadership.
Key Responsibilities
Develop and lead a comprehensive fundraising strategy that builds United Way Winnipeg's established campaign model, introducing innovative approaches to donor engagement, participation, retention, and sustainable revenue growth.
Design and deliver a cohesive, engaging donor experience, ensuring every interaction reflects United Way Winnipeg's values, builds meaningful connections, and inspires long-term commitment and participation.
Provide strategic leadership and oversight of the annual Campaign for the Community Fund, establishing performance measures that balance fundraising results with donor participation, retention, and long-term campaign sustainability.
Identify emerging trends and opportunities within the philanthropic landscape, adapting fundraising strategies to changing workplace environments, donor expectations, and generational giving patterns.
Champion a creative, donor-centred approach to philanthropy, designing meaningful experiences across campaigns, events, workplace initiatives, and stewardship activities.
Build and steward lasting relationships with donors, corporate partners, and community leaders, strengthening engagement across Winnipeg's business, labour, nonprofit, and community sectors to expand participation and philanthropic support.
Foster strong partnerships with Campaign Chairs, Cabinet members, Employee Campaign Chairs, and other volunteers.
Lead, coach, and develop employees through a values-based leadership approach that fosters collaboration, creativity, accountability, and professional growth.
Experience and Background
Senior leadership experience in fundraising, philanthropy, development, or revenue generation, with a demonstrated record of building successful strategies, strengthening relationships, and achieving sustainable growth.
Proven experience leading and developing teams, including building organizational capacity, managing through change, and fostering a collaborative, high-performing, and values-driven culture.
Demonstrated creativity and innovation in developing engagement strategies and experiences that inspire participation, strengthen connections, and translate an organization's purpose into action.
Proven ability to develop and execute strategic plans, establish performance measures, and use data, donor insights, and CRM systems to inform decision-making and improve fundraising effectiveness.
Exceptional relationship-building and communication skills, with the ability to engage and influence diverse stakeholders across corporate, labour, nonprofit, and community environments.
Experience leading organizational transformation, including assessing existing structures, identifying opportunities for improvement, and guiding teams through periods of change and uncertainty.
A genuine commitment to community impact and values-based leadership, with the ability to inspire others, foster belonging, and create meaningful connections between donors and the causes they support.
United Way Winnipeg welcomes leaders who bring diverse professional experiences and perspectives to philanthropy, including those who have successfully built and led organizations or developed innovative approaches to engagement and revenue growth.
About United Way WinnipegUnited Way Winnipeg (UWW) was established in 1965 through a partnership between the Winnipeg Chamber of Commerce and the Winnipeg Labour Council, building on an even longer history of community fundraising. That foundational partnership continues to shape how United Way Winnipeg responds to complex social issues through community leadership, strategic investment, and impactful programs. Thousands of volunteers contribute their time, knowledge, leadership, and passion to guide and strengthen the organization's work.
The Board of Trustees and its many Committees and Councils provide essential community-led guidance, oversight, and vision. These include the Resource Development Committee, Campaign Cabinet, Major Donor Cabinet, Campaign Advisory Committee, and Council for Indigenous Relations, among others. Working alongside staff, these volunteer leaders help shape fundraising strategies, strengthen community partnerships, and guide investment in the programs and agencies that support Winnipeggers. Together, this network of volunteers, donors, and community partners represents the collective leadership and generosity that define United Way Winnipeg.
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