The Organization:

Summit Search Group has been retained by Big Brothers Big Sisters of Winnipeg (BBBSW) on the recruitment of their next Executive Director. With a proud history rooted in serving the local community, BBBSW provides opportunities for children and youth facing adversity to build meaningful, supportive relationships with caring adult mentors. These relationships create positive outcomes in self-esteem, school engagement, social connection, and long-term success.

Each year, BBBSW supports approximately 300 young people through a diverse mix of programming, including traditional one-to-one matches, In-School Mentoring, group programs, and the PRISM program, which provides safe and inclusive support to LGBTQ+ youth. Their work is made possible through the efforts of 8–10 dedicated staff, a committed volunteer base, and the generosity of donors and funders. Operating from their owned facility on Ellice Avenue, they provide program space and collaborate with community partners by sharing their office space.

BBBSW is at an important juncture, navigating leadership transition, strategic planning for long-term sustainability, and the exploration of potential partnerships and collaborative opportunities. This moment offers an exciting opportunity for a leader who is passionate about youth empowerment and ready to shape the next chapter of BBBSW’s impact.

The Position:

The Executive Director (ED) provides overall leadership and direction for Big Brothers Big Sisters of Winnipeg, balancing strategic vision with hands-on operational management. Reporting to the Board of Directors, the ED is responsible for guiding staff, managing programs, ensuring compliance, overseeing finances, and driving fund development. A key part of this role involves building and maintaining strong relationships with donors, community stakeholders, and the national Big Brothers Big Sisters federation.

The ED will act as the face of the organization, representing BBBSW in the community, strengthening partnerships, and ensuring youth and families receive high-quality programming. The role requires a leader who is both strategic and pragmatic, someone who can inspire staff and volunteers, safeguard organizational sustainability, and drive growth in an environment of evolving funding landscapes and compliance requirements.

The ideal candidate is a strategic, values-driven leader with proven experience in nonprofit or community-based organizations, who can balance visionary growth with hands-on operational management.

Leadership and Organizational Management:

• Provide strategic vision and day-to-day leadership to ensure the effective delivery and continuous improvement of all youth programs.
• Build and maintain a positive, collaborative, and inclusive organizational culture that empowers staff and volunteers.
• Recruit, supervise, and support staff while ensuring role clarity, performance accountability, and opportunities for growth.
• Guide long-term planning efforts, balancing program innovation with sustainability and financial prudence.

Financial Stewardship and Fund Development:

• Oversee annual budgeting, financial monitoring, reporting, and compliance with funders, regulators, and the Board of Directors.
• Ensure the organization maintains strong financial health by diversifying and growing revenue streams, including government contracts, community grants, private donations, and special events.
• Lead donor relations, sponsorship cultivation, and community fundraising, acting as a trusted and visible representative to supporters.
• Proactively manage organizational risks, including insurance, liability, and compliance obligations.

Governance, Partnerships, and Community Impact:

• Serve as the primary liaison to the Board of Directors, ensuring strong governance, timely communication, and informed decision-making.
• Ensure compliance with all national Big Brothers Big Sisters federation standards, government requirements, and reporting obligations.
• Act as the organization’s ambassador within Winnipeg, strengthening partnerships with schools, community organizations, funders, and local leaders.
• Advocate for youth mentorship, equity, and inclusion, ensuring BBBSW remains a trusted voice and champion for young people.

Qualifications:

• Proven leadership experience in nonprofit, social service, youth-serving, or community-based organizations; prior experience as an Executive Director or senior manager is a strong asset.
• Demonstrated ability to manage budgets, financial reporting, and compliance requirements with government funders and regulatory bodies.
• Successful track record in fund development, including donor relations, grant writing, sponsorship, and community fundraising.
• Strong skills in staff leadership, team building, and fostering an inclusive, high-performance workplace culture.
• Excellent communication and relationship-building abilities, with the capacity to engage diverse stakeholders including youth, families, donors, community partners, and board members.

Big Brothers Big Sisters of Winnipeg operates on Treaty No. 1 Territory, the traditional lands of the Anishinaabe, Cree, Oji-Cree, Dakota, and Dene peoples; as well as the homeland of the Metis Nation. We further acknowledge the water of which we drink comes from the Anishinaabe First Nation of Shoal Lake.

We respect the Treaties formed on these territories and acknowledge that We Are All Treaty People. We recognize the long-term effects of colonization and the harmful legacy of the residential schools endured by Indigenous peoples. We commit to making space for Indigenous voices, to celebrate Indigenous culture, and to honour Indigenous heritage. We are Bigger together and we will work in partnership with Indigenous communities toward justice, equity, and reconciliation.

For more information, or to submit your resume, please reach out to Jessica Willis, Partner and Senior Recruitment Consultant at Summit Search Group, Jessica.Willis@summitsearchgroup.com

Summit Search Group has a strong commitment to Diversity, Equality and Inclusion. We strive for continuous development, modeling, inclusive behaviors and proactively managing bias throughout our process.