Executive Director

Position Type: Full-time | Hybrid (Toronto-based)

The Shoebox Project for Women is a national Canadian charity dedicated to uplifting and empowering women and gender‑diverse people experiencing or at risk of homelessness. Through in‑kind support, education, and community participation, we work alongside shelters, community agencies, volunteers, and partners across Canada to ensure women have access to essential items and support when they need it most. With a strong grassroots chapter network and a respected national brand, The Shoebox Project is entering an exciting new chapter focused on growth, sustainability, and deepening impact.

The Executive Director is responsible for achieving the organization’s overall goals, implementing and executing policies and procedures, providing organizational leadership, strengthening financial sustainability, and ensuring operational excellence across a national, volunteer chapter‑based charity. The role blends big‑picture strategy with hands‑on execution of day‑to‑day operations and tasks and is ideally suited to a leader who is equally comfortable in the boardroom, with donors, and rolling up their sleeves alongside staff and volunteers.

• Lead and execute a comprehensive fundraising strategy to grow and diversify revenue, including individual and monthly giving, corporate partnerships and sponsor ships, foundations and grants, and major gifts.
• Serve as a key relationship‑builder and fundraiser with donors, funders, and partners.
• Strengthen fundraising systems, data, and performance metrics to support long‑term sustainability.

• Lead the execution of the organization’s mission, vision, and strategic plan in partnership with the Board of Directors.
• Serve as a national ambassador and advocate for the organization and its mission.

• Oversee the financial health of the organization, including budgeting, forecasting, cash flow, and financial reporting.

• Execute day‑to‑day operations, including HR, administration, and policy development.
• Serve as the organization’s primary spokesperson, strengthening public profile through media, communications, and partnerships.
• Lead, mentor, and support a small head office staff team and a national network of volunteer chapter leaders and their team volunteers, balancing grassroots engagement with national consistency.
• Champion equity, inclusion, and belonging across all levels of the organization.

• Work closely with the Board of Directors and Sub‑Committees to support strong governance, strategic decision‑making, and accountability.

You are a self‑directed, operational leader who thrives in a flat organizational structure. You are motivated by mission, grounded in strong business and financial discipline, and energized by building relationships that drive impact. You are a results‑oriented, collaborative, and strategic leader who brings both heart and rigor to completing the work in a hands‑on environment.

• 5–7+ years of senior experience, preferably in the nonprofit, charitable, or social impact sector.
• Demonstrated success in fundraising, such as through donor stewardship, major gifts, and corporate partnerships.
• Strong financial acumen with experience managing budgets and preparing financial reporting.
• Excellent communication skills, with confidence as a public spokesperson.
• Exceptional relationship building with experience leading small teams and managing volunteers in distributed or chapter‑based models.
• A deep commitment to equity, inclusion, and dignity‑based approaches to supporting women.

• Experience leading or working within a national organization, previous experience working with a Board of Directors.
• Knowledge of issues related to homelessness, poverty, and gender equity.

• Competitive salary plus benefits
• Hybrid work environment
• Governance support through an engaged Board of Directors
• Opportunity to make an impact for women across…