Supervisor, Winter Programs, FT

Employment Type: Full-time, Long Term Contract
Department : Shelter and Respite Services
Union: Excluded
Salary: Up to $65,000 annually
File #: 26-SRS-30 (10 OPEN)
Posting Date: October 5, 2026
Posting Close : October 19, 2026
Reason for vacancy: New Hire

Position Summary
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. This position plays a key leadership role in ensuring a safe, supportive, and client-centered environment for all staff and program participants.

The hours of work are Monday to Friday with rotating shifts as follows:

• 7:00 a.m. – 3:00 p.m.
• 3:00 p.m. – 11:00 p.m.
• 11:00 p.m. – 7:00 a.m.

 

Responsibilities

Operational Leadership

• Plan, coordinate, and monitor all operational activities within the assigned portfolio to ensure efficient service delivery.
• Lead and participate in committees and task groups as required.
• Contribute to the development of the department’s annual operating plan.
• 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.
• Adhere to the expenditure and accounting procedures outlined by the Finance Department.
• 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.
• Review the communication logbook and follow up on new intakes, incidents, and important updates.
• Review and update the bed list daily to ensure accuracy and bed availability; follow up with staff to confirm completion.
• Follow up with clients requiring additional support, referrals, or service coordination.
• Provide coverage and support to staff during lunch breaks or periods of high activity as needed.
• Review and maintain TTC PRESTO card balances daily, ensuring cards are topped up to $30 as required.
• 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.

People and Culture

• Partner with the People and Culture Department on recruitment, onboarding, and labour relations matters.
• 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.
• Administer disciplinary processes fairly and consistently within established timelines.
• 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.

Organizational Accountability

• Collaborate effectively with Dixon Hall staff, volunteers, and community partners.
• Operate in a client-focused, efficient, and solution-oriented manner.
• Ensure compliance with the Occupational Health & Safety Act and the Ontario Fire Code.
• Complete workplace incident and injury reports as required.
• Support the Occupational Health & Safety Committee in meeting all legislative obligations.
• Oversee fire and emergency drill implementation and ensure proper follow-up and documentation.
• Perform other related duties as assigned.

Qualifications

• Bachelor of Social Work, Social Service Worker Diploma, or related degree/diploma required.
• Emergency First Aid/CPR certification preferred.
• Minimum of three (3) years of supervisory or related experience, preferably in a unionized environment.
• Experience working with individuals experiencing homelessness or barriers to housing stability.
• Strong crisis intervention, de-escalation, counselling, and conflict resolution skills.
• Knowledge of the systemic, political, and social causes of homelessness and poverty in Toronto.
• Excellent interpersonal and communication skills, with the ability to engage effectively with staff, clients, and partners.
• Strong organizational, administrative, and computer proficiency.
• Ability to exercise sound judgment, flexibility, and creativity in a fast-paced environment.
• Exceptional multitasking, time management, writing, and editing abilities.
• Proven capacity to work collaboratively across sectors (public, private, non-profit, and community-based organizations).
• Self-directed, with the ability to work both independently and as part of a multidisciplinary team.
• Must be legally eligible to work in Canada.
• Must provide a Vulnerable Sector Screening Check with a satisfactory result meeting agency requirements.

Dixon Hall may use Artificial Intelligence-assisted tools during the recruitment process to support efficiency and consistency. Final hiring decisions are made by the Human Resources team.

 

Dixon Hall is dedicated to fostering an inclusive selection process and work environment, guided by their Race Relations and Employment Equity Policies. If selected for an interview, please inform the hiring manager or the People and Culture team at View email address on dixonhall.applytojob.com of any accommodations you may require during the interview process.

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.