Supervisor, Drop-In and Outreach

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Supervisor, Drop-In and Outreach

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Supervisor, Drop-In and Outreach

Outreach Department

Onsite

Full Time, Permanent

Level 8

Requisition Number: DIO-2026-004

Covenant House helps youth ignite their potential and reclaim their lives. As Canada’s largest agency serving youth who are homeless, trafficked or at risk, we offer the widest range of services to hundreds of young people every day.

More than a place to stay, we provide life-changing care with unconditional love and respect. We meet youth’s immediate needs and then we work together to achieve their future goals. We offer 24/7 crisis shelter transitional housing options on-site and, in the community, health and well-being support, training and skill development, and ongoing care once youth move into the community.

For over 40 years, Covenant House has been dedicated to its mission of serving youth on the street and to protect and safeguard all youth with absolute respect and unconditional love. Since 1982, Covenant House has supported more than 100,000 young people.

Overview:
The Drop-In and Outreach Supervisor ensures that Drop-In and Outreach staff and participants can access a safe space and low barrier drop-in program to get their immediate and basic needs met. The Supervisor manages and oversees the work of all youth workers. In addition to coordinating the activities of each shift, the Supervisor is responsible for managing crisis and emergency situations related to young people, staff, the facility and the community.

We are currently recruiting for 1 Full-time, Permanent Supervisor, Drop-In and Outreach. This is a replacement position within the organization.

Responsibilities:

People Management

• Ensure that all staff implement the policies and procedures of Covenant House.
• Ensure all shifts are filled to ensure safety of the program for staff and young people.
• Provide regular supervision and leadership to direct reports and volunteers, supporting staff development using a trauma-informed approach that facilitates a positive, inclusive, and collaborative work environment.
• Ensure that human resource practices are consistent with agency policies and compliant with relevant legislation.
• Facilitate program teams meetings.
• Demonstrate awareness of, and ensures staff work in accordance with organization health and safety policies and procedures.
• Ensure payroll information is accurate in Payworks and update Volunteer Services of hours and other volunteer related data.

Facilities Management

• Responsible for safety, security and contents of the Drop-In space during program hours including the safe evacuation of the building in the event of fire, or other facility issues that jeopardize the safety of residents.
• Monitor youth behavior in program and ensure that threats to the safety of our youth are properly managed by staff.
• Program Management and Administration
• Ensure that services delivered to young people are consistent with Covenant House principles and are responsive to the needs of young people.
• Collaborate with the Drop-In Manager and other departments to identify gaps in service; development and design of new programs that align with the strategic plan and annual service plans.
• Develop partnerships and coordinate services with comparable community programs.
• Quality assurance of program data collection, key performance indicators and monitoring program trends.
• Ensure documentation is complete, and records are compliant with agency guidelines.
• Monitor significant incidents, and discharges; attending case review and team meetings as required.
• Provide as-needed support to staff in decision making, problem solving, and crisis navigation ensuring good clinical judgement that meets the needs of young people.
• Manage petty cash float, TTC tickets and cab vouchers.
• Maintain and monitor food bank numbers and supplies.

Organizational Activities

• Participation in internal and external committees.
• Responsible for taking a lead role in special program projects as assigned.

Qualifications

• 1-2 Years Supervisory experience in a shelter or drop in setting
• Child and Youth Work Diploma or Bachelor of Arts in related subject (i.e. Social Work)
• Possess an understanding of the issues of youth homelessness and human trafficking and the barriers young people experiencing homelessness and/or human trafficking face in relation to employment, education, social inclusion, mental health, and wellbeing.
• Demonstrated ability to work with a trauma-informed approach and an understanding of and personal commitment to anti-oppressive practices, and anti-racism practices.
• Non-violent crisis intervention training and standard first aid training; Suicide intervention training is an asset.
• Demonstrated leadership, supervision skills and ability to develop an effective team is an asset.
• Demonstrated exceptional level of interpersonal, communication, and organizational skills.
• Dedication and openness to continued learning and improvement.
• Proficiency in Microsoft Office 365 required.

Don’t meet every requirement? Studies have shown that women and people of color are less likely to apply to jobs unless they meet all qualifications. If you are excited about the role but your resume doesn’t align perfectly with every qualification in the description, apply anyway. You may still be the right candidate for this or other roles.

What we Offer:

• Meaningful work.
• Competitive compensation.
• Benefits such as Health, Dental, Vision, Personal Days, Employee Assistance Program, Tuition Reimbursement and more.
• Employee perks which include discounts on gym membership, city bike rentals, auto & home insurance and more.

Interested candidates are welcome to apply directly to this posting on or by August 21, 2026. Only those selected to move forward in our recruitment process will be contacted. No agencies or phone calls please.

Use of AI and Technology in the Hiring Process

Covenant House Toronto does not use artificial intelligence (AI) to make or inform hiring decisions. However, we do use an external applicant tracking system (ATS) to help manage applications efficiently.

While our ATS may apply automated filters or sorting functions, all applications are reviewed and evaluated by human recruiters. No hiring decisions are made by AI.

Commitment to Equitable Recruitment

At Covenant House Toronto we believe in a workplace culture of inclusion that is welcoming, respectful and safe for all staff. It is critical to Covenant House Toronto success to eliminate barriers and promote the inclusion of equity groups. Equity groups have been, and continue to be, underrepresented and marginalized in the workforce, leadership roles, and in some specific occupations. Equity groups include but may not be limited to Indigenous persons, racialized people, gender diverse people, 2SLGBTQIA+ people, and people with disabilities.

In accordance with the Ontario Human Rights Code, Accessibility for Ontarians with Disabilities Act and Covenant House Policy on Accommodation, a request for accommodation will be accepted as part of the Covenant House recruitment process.

Please visit our careers page to see more job opportunities.