Matthew Cutler

Matthew Cutler has served as President and CEO of United Way Winnipeg since August 2025, bringing together a lifetime of grassroots community involvement and more than two decades of executive leadership in the public sector—including roles at the Canadian Museum for Human Rights, in Manitoba’s Public Service, and with the Toronto Public Service.

His first year has been defined by deep listening and deliberate action. Matthew has invested in understanding the breadth and complexity of Winnipeg’s social landscape—from the community agencies on the front lines of the city’s most pressing challenges, to the donors and volunteers whose generosity powers the movement. That learning has informed a renewed organizational design, a clearer operational framework, and a leadership team built for the adaptive, collaborative work ahead.

Having worked for and volunteered with many United Way agencies, he understands firsthand the vital role these organizations play in people’s lives and in building strong, caring neighbourhoods. His graduate training in organizations and leadership theory, combined with his experience leading complex institutions through periods of significant change, enables him to align strategy and vision with community need—especially at a moment when that alignment has never mattered more.

At United Way Winnipeg, Matthew leads a movement: thousands of volunteers, more than 80 staff, and a network of over 125 local agencies and initiatives working together to strengthen our city’s social safety net. Guided by the 2025–2030 Strategic Plan, his leadership is marked by heart, strategy, and integrity—anchored in the belief that lasting social change is achieved through inclusive collaboration, strong relationships, and a deep respect for community.

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Brief Version

Known for combining heart, strategy, and integrity to create lasting social change, Matthew Cutler has served as President and CEO of United Way Winnipeg since August 2025. Bringing both grassroots community experience and over two decades of executive leadership, he is honoured to lead a century-long movement of thousands of volunteers, more than 80 staff, and a network of over 125 local agencies that work united toward a Winnipeg where everyone has pathways to heal, grow, and thrive.

Short Version

Matthew Cutler has served as President and CEO of United Way Winnipeg since August 2025. With more than 20 years of leadership in the public sector and a lifetime of grassroots community involvement, he brings both breadth of executive experience and a deep respect for community. His first year has been marked by deliberate listening—to the city’s agencies, donors, volunteers, and the people they serve—and by building the organizational conditions needed to deliver on United Way Winnipeg’s 2025–2030 Strategic Plan. Matthew has worked for and volunteered with many United Way agencies, led large teams, and built the kind of cross-sector partnerships that deliver impact at scale. Today he leads a movement of thousands of volunteers, more than 80 staff, and a network of over 125 local agencies working together toward a Winnipeg where everyone has pathways to heal, grow, and thrive.