Executive Director

About The Shoebox Project for Women

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 Opportunity

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.

As the successful candidate, you will spend your days on:

Fundraising & Revenue Generation

• Lead and execute a comprehensive fundraising strategy to grow and diversify revenue, including individual and monthly giving, corporate partnerships and sponsorships, 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.

Strategic & Organizational Leadership

• 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.

Financial & Business Leadership

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

Operations, Communications & External Relations

• 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.

People, Culture & Chapter Leadership

• 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.

Board Governance & Collaboration

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

The Ideal Candidate

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.

You bring:

• 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.

You might also bring:

• 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.
• Bilingualism (English/French).

We offer:

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

Why Join Us?

This is a pivotal leadership role with a respected national charity that is poised for growth. As Executive Director, you will have the opportunity to shape the future of The Shoebox Project for Women and work alongside a passionate volunteer and donor community committed to dignity, compassion, and meaningful impact across Canada.

This is a full-time, hybrid position with an expectation of working from the Toronto head office approximately 50% of the time. The role offers a competitive salary range of $85,000–$115,000 per year, commensurate with experience, plus benefits.

How to Apply

Qualified candidates are invited to submit a resume and cover letter outlining their interest in the role to the Chair of the Board at chair@shoeboxproject.com by February 27, 2026 at 5:00 p.m. Applications will be reviewed on a rolling basis.

We appreciate the interest of all applicants; however, only those selected to move forward in the recruitment process will be contacted. The comprehensive job description will be provided to candidates invited to interview.

The Shoebox Project for Women is committed to equity, inclusion, and diversity. We welcome applications from all qualified candidates and all inquiries and applications will be kept strictly confidential. We are happy to provide accommodations throughout the recruitment process upon request.