Employment Type: Part-time, Long Term Contract Posting Date: October 5, 2026 Posting Close: October 19, 2026 The Supervisor, Winter Programs reports to the Manager, Winter Programs and is responsible for providing supervisory and operational support to staff while overseeing the day-to-day operations of assigned sites. Hours of work are Saturday - Sunday with rotating shifts as follows: ~Support and report on departmental projects and initiatives. Participate in the on-call rotation as required.

Foster and maintain community partnerships to strengthen service delivery and policy development. Actively engage in shelter and housing networks within the community and the City of Toronto. Oversee procurement, supply control, and payroll processes for assigned sites.

Manage property and facility-related issues within the assigned portfolio. Site Operations and Daily Oversight Conduct daily morning check-ins with frontline staff to receive shift change updates and review shift reports. Participate in shift changes to ensure consistent communication and continuity of care between shifts.

Organize and facilitate monthly staff meetings and resident meetings to encourage communication and engagement. Record, finalize, and post minutes for all monthly staff and resident meetings in a timely manner. Supervise, coach, and mentor staff to ensure high-quality service delivery and professional growth.

Conduct annual performance evaluations, setting clear goals and expectations. Address performance and behavioural concerns promptly, in alignment with the collective agreement.



Promote understanding of the WSIB claim process and the importance of early return-to-work programs.

Monitor active WSIB claims and support early and safe return-to-work initiatives. Collaborate effectively with Dixon Hall staff, volunteers, and community partners. Ensure compliance with the Occupational Health & Safety Act and the Ontario Fire Code.

Oversee fire and emergency drill implementation and ensure proper follow-up and documentation. Bachelor of Social Work, Social Service Worker Diploma, or related degree/diploma required.

Experience working with individuals experiencing homelessness or barriers to housing stability. Knowledge of the systemic, political, and social causes of homelessness and poverty in Toronto. Robust organizational, administrative, and computer proficiency. Exceptional multitasking, time management, writing, and editing abilities. Proven capacity to work collaboratively across sectors (public, private, non-profit, and community-based organizations).

Dixon

Hall may use Artificial Intelligence-assisted tools during the recruitment process to support efficiency and consistency.

Dixon

Hall is dedicated to fostering an inclusive selection process and work environment, guided by their Race Relations and Employment Equity Policies. To achieve their goal of inclusivity and diversity, Dixon Hall actively seeks exceptional candidates from varied backgrounds and with lived experiences. Individuals who self-identify as being from marginalized communities, including Indigenous peoples, racialized persons, persons with disabilities, and those from the 2SLGBTQIA+ community or who have experienced homelessness, are strongly encouraged to apply.

📌 Supervisor, Winter Programs, PT (Toronto)
🏢 Dixon Hall
📍 Toronto