Assistant Regional Director

Benefits

• Generous vacation including all Jewish holidays
• Great culture – we’re always here to help each other out!

Since 2006, Chai Lifeline Canada has been providing services to children and families who are impacted by chronic or life‑threatening illness. In this dynamic role, you will positively impact families as they navigate through difficult times and contribute to a more caring and connected community. At Chai Lifeline Canada, you will be part of a dynamic team that is dedicated to living our core values and leading with integrity and mutual respect.

We provide care and love to families in need and, in doing so, we carry out our roles with empathy, dedication and humility.

The Assistant Regional Director is a senior operational leader responsible for the day‑to‑day management, growth, and sustainability of Chai Lifeline Canada’s Toronto operations. Reporting directly to the Executive Director, this role focuses on operational excellence, team leadership, fundraising execution, and community engagement, ensuring that the Toronto office functions efficiently, professionally, and in alignment with national strategy and organizational values. This is a hands‑on role, and the Director will be personally involved in fundraising planning, execution, and relationship management, with the support of the team.

This position is well suited for an experienced nonprofit leader who thrives in a hands‑on environment, understands that fundraising and operations are inseparable, and is comfortable balancing internal management with external relationship‑building. The Assistant Regional Director is accountable not only for outcomes, but for clear systems, documented processes, and consistent reporting.

• Office Operations & Execution (Primary Focus)
  • Oversee in tandem with the executive director the full operational functioning of the Toronto office, including administration, finance coordination, programs, fundraising activity, and compliance
  • Translate organizational strategy into clear operational plans, timelines, and deliverables
  • Ensure that all key functions operate with clear and documented systems, procedures, accountabilities, and workflows
  • Maintain accountability for deadlines, follow‑through, and measurable outcomes
  • Identify inefficiencies and proactively implement improvements
  • Lead and execute Toronto‑based fundraising initiatives, including events, campaigns, donor cultivation, sponsor ships, and community appeals
  • Actively manage and grow relationships with donors, funders, and community partners
  • Work closely with the Executive Director to align Toronto fundraising efforts with national strategy
  • Ensure accurate tracking, follow‑up, and stewardship of donors
  • Integrate fundraising messaging with program impact and storytelling
• Financial Oversight & Budget Management
  • Manage the Toronto office budget in alignment with organizational goals and approved financial plans
  • Ensure responsible stewardship of funds and adherence to financial controls
  • Lead and support Toronto‑based staff with clarity, consistency, and accountability
  • Foster a professional, respectful, and mission‑driven work environment
• Program Oversight & Service Quality
  • Ensure Toronto‑based programs are delivered effectively, compassionately, and in alignment with Chai Lifeline standards
  • Support program staff in planning, evaluation, and growth
  • Maintain strong relationships with hospitals, referral sources, and partner agencies
  • Monitor service delivery to ensure families receive timely and appropriate support
• Volunteer & Community Leadership
  • Oversee and support Toronto’s volunteer structure, including committee chairs and key volunteers
  • Ensure volunteers are well‑supported, effectively utilized, and aligned with organizational goals
  • Serve as a visible representative of Chai Lifeline in the Toronto community
  • Build strong relationships with community leaders, institutions, and stakeholders
• Reporting, Communication & Accountability
  • Report directly and regularly to the Executive Director with clear updates on operations, fundraising, staffing, and priorities
  • Provide accurate and timely information to support leadership decision‑making
  • Maintain…