JOB TITLE: Housing Outreach Worker
POSITION TYPE: Full-time Contract Position (35 hours/week)
START DATE: 1 June 2026
END DATE: 31 March 2028
REPORTING TO: Community Programs Manager
COMPENSATION TYPE: Salary & benefits
OFFICE LOCATION: Newmarket, with work throughout York Region
POSITION SUMMARY
CAYR COMMUNITY CONNECTIONS (CAYR) strives to create safe, confidential, and inclusive spaces and services in York Region where people can access dignified support and meaningfully engage in self-determined pathways to well-being. We envision an informed, healthy, stigma-free, and compassionate community.
We offer specialized and combined programs for people living with HIV/AIDS (newly diagnosed to long-term survivors); people affected by or at risk of HIV and Hep C; people who use drugs; people who identify as 2SLGBTQ+; and people supporting vulnerable and marginalized community members.
The Housing Outreach Worker plays a key role in delivering the CAYR Connecting to Home program, a Housing First–informed initiative that combines low-barrier outreach, harm reduction, and housing support for individuals experiencing or at imminent risk of homelessness in York Region.
Working as part of a multidisciplinary team, the Outreach Worker engages individuals in encampments, public spaces, shelters, and community settings, with a focus on building trust and facilitating pathways to housing stability. The role prioritizes individuals experiencing chronic homelessness, mental health challenges, substance use, and those from equity-deserving communities, including Black and 2SLGBTQ+ populations.
Key Responsibilities
Outreach & Engagement
- Conduct regular, proactive outreach in encampments, public spaces, shelters, and community settings across York Region
- Build trusting, non-judgmental relationships using trauma-informed, harm reduction, and anti-oppressive approaches
- Identify individuals experiencing or at imminent risk of homelessness and support initial engagement, through system coordination and community engagement
- Provide comprehensive case management support to program participants, including conducting needs assessments, developing individualized housing and support plans, coordinating referrals to community resources, monitoring participant progress, advocating for client needs, maintaining accurate case documentation, and supporting individuals in achieving housing stability and overall well-being.
Housing Support & System Navigation
- Support participants in accessing housing through Coordinated Access and other referral pathways
- Assist with housing applications, lease agreements, and system navigation including Ontario Works (OW) and Ontario Disability Support Program (ODSP) applications.
- Work collaboratively with Housing Program Specialist (e.g. CMHA) to support housing placement and retention
Prevention & Diversion
- Identify individuals experiencing unsheltered homelessness or at risk of losing housing.
- Provide basic support and referrals related to eviction prevention, discharge planning, and housing stabilization
Client Support Services
- Distribute practical supports (e.g., food, clothing, tents, sleeping bags, hygiene supplies, transit support) in collaboration with CAYR’s Harm Reduction team
- Facilitate access to health care, mental health supports, substance use services, and other community resources
Collaboration & Systems Work
- Collaborate with CAYR’s internal teams and external partners including shelters, housing providers, health services, and community agencies
- Participate in Coordinated Access processes and relevant community tables as required
- Support continuity of care for individuals transitioning between systems (e.g., hospital, corrections, shelters)
Documentation & Reporting
- Maintain accurate and timely client records using systems such as HIFIS
- Track outreach activities, service delivery, and participant outcomes
- Contribute to program evaluation, data collection, and reporting requirements
Qualifications
- As a requirement of this position the successful candidate must have a working knowledge of working with marginalized communities or identify as a member of one or more of the communities served (e.g. People Living with HIV, 2SLGBTA+ Individuals, People with lived experience of homelessness, incarceration or substance use)
- Diploma or degree in Social Work, Social Services, or a related field, or equivalent lived/living experience
- Minimum 2 years’ experience in outreach, homelessness services, harm reduction, or related fields
- Strong understanding of Housing First, harm reduction, and trauma-informed care
- Experience working with people who use substances, individuals experiencing homelessness, and equity-deserving populations
- Knowledge of York Region housing and social service systems is an asset
- Valid driver’s license and ability to travel throughout York Region
- Knowledge of HIFIS
Core Competencies
- Ability to maintain confidentiality and strong working boundaries
- Strong relationship-building and engagement skills
- Ability to work independently in community-based settings
- Non-judgmental, anti-oppressive, and culturally responsive practice
- Crisis intervention and de-escalation skills
- Effective communication and documentation skills
Working Conditions
- Regular outreach in outdoor and community settings, including encampments
- Evening and occasional weekend work may be required (Prior Approval)
- Exposure to challenging environments; adherence to safety protocols required
Other
- Adhere to CAYR’s policies and procedures.
- Other duties as assigned by Program Manager
Compensation
- $49,740 per annum, pro-rated (as per approved funder program budget)
- benefits
To apply, please submit cover letter and resume highlighting qualifications and experience by:
- Email to [email protected] with subject line Housing Outreach Worker Position in the subject line
CAYR COMMUNITY CONNECTIONS promotes the principles of anti-oppression and adheres to the tenets of the Ontario Human Rights Code. We encourage applicants with lived experience of substance use, HIV/AIDS, and/or Hep C. We also encourage people of all races, ethnic origins, religions, abilities, sexual orientations, gender identities and expression.
We thank all applicants. However, only those who are to be interviewed will be contacted.
Pay: $49,740.00 per year
Benefits:
Work Location: Hybrid remote in Newmarket, ON L3Y 3E3
