Reporting to the Executive Director, the Welcoming Streets Program Supervisor & Member Liaison provides operational leadership for the Downtown Kingston BIA's street outreach initiative while serving as its primary bridge to the business community. This role is equal parts people manager and relationship builder: on one side, supervising and supporting a frontline outreach team through scheduling, performance management, training, and day-to-day coordination; on the other, maintaining a proactive and visible presence with BIA members and their employees — checking in, building trust, and translating the realities of the street into practical guidance and programming that members can act on. The ideal candidate brings strong supervisory instincts and a genuine ease with people across very different contexts, from supporting a team doing difficult frontline work to walking into a busy retail environment and starting a conversation.
KEY RESPONSIBILITIES
Team Leadership & Supervision
- Supervise, mentor, and support Welcoming Streets outreach staff, fostering a team culture grounded in compassion, accountability, and continuous learning.
- Develop and manage staff scheduling to ensure consistent and effective outreach coverage across the downtown core.
- Conduct regular performance reviews and provide ongoing coaching to support staff development, program quality, and the well-being of the outreach team.
- Lead the coordination of outreach programming and training initiatives, ensuring alignment with the BIA's values and operational goals.
- Identify emerging needs and trends in the downtown community and adapt programming, accordingly, reporting findings and recommendations to the Executive Director.
- Ensure accurate records of outreach activities and partnership engagements are tracked to support program evaluation, reporting, continuous improvement and funding.
Member Liaison & Business Community Engagement
- Serve as the primary point of contact for BIA members on matters related to the Welcoming Streets program, building trusted, ongoing relationships through proactive outreach and regular check-ins.
- Conduct warm visits to member businesses and their employees — not as crisis response, but as relationship-building — to understand their experiences, answer questions, and develop programming that reflects their needs.
- Deliver training and education to BIA members and their staff, equipping them with practical knowledge, resources, and strategies to respond compassionately and confidently to social challenges in the downtown environment.
- Act as a knowledgeable and approachable advocate for the Welcoming Streets initiative, representing the program with credibility across the business community.
- Gather and synthesize member feedback to inform program development and communicate business community perspectives to the outreach team.
Navigating Competing Needs with Compassion and Clarity
At the heart of this role is the ability to hold two equally legitimate sets of needs in tension — and to do so with integrity. The individuals our outreach team serves are often among the most vulnerable members of our community, and their dignity, safety, and access to support matter deeply to this organization. At the same time, BIA members, their employees, and the visitors who animate downtown Kingston deserve to work, shop, and gather in an environment that feels welcoming and safe. These needs are not opposites, but they are not always easy to reconcile. The people who thrive in this kind of work are those who find genuine meaning — and even moments of joy — in the small wins, the relationships built over time, and the knowledge that showing up consistently makes a difference, even when outcomes are uncertain, or not what you hoped. The ability to thrive with unresolved tension — knowing that some competing interests cannot be easily reconciled — and to help others do the same, is critical to success for this position.
Partnership & Community Coordination
- Oversee coordination with AMHS dedicated outreach staff and the broader network of social service providers, healthcare agencies, and community organizations.
- Collaborate with City of Kingston Bylaw Officers and Kingston Police when situations require additional support.
- Support connections to partner agencies including Home Base Housing, the Integrated Care Hub, and Street Health.
- KEY REQUIREMENTS
Leadership & People Management
Proven ability to supervise, coach, and motivate a team in a dynamic, community-facing environment. Strong organizational skills with experience managing scheduling, conducting performance reviews, and building a collaborative and supportive team culture. Experience leading people through emotionally demanding work is a significant asset.
Relationship Building & Community Engagement
Exceptional interpersonal skills and a genuine ease with people across diverse contexts — from a frontline outreach worker navigating a difficult situation to a business owner looking for practical guidance. Comfort walking into unfamiliar environments, initiating conversations, and building trust over time is essential to this role.
Understanding of Social Issues & Outreach Contexts
A working knowledge of the issues facing individuals experiencing homelessness or living with mental health and addiction challenges, and an understanding of the outreach landscape. Direct outreach experience is not required, but the ability to credibly support, debrief, and guide a team doing that work is essential.
Communication & Facilitation
Confident communicator capable of delivering training, facilitating difficult conversations, and representing the program across a wide range of audiences — from business owners and their staff to community partners and City stakeholders.
Financial Literacy
- Data and reporting: maintain and report on program outcome data (interactions, referrals, member engagement) to support funder reporting and grant applications.
- Budget/resource management: Understanding of financial reports, budget vs. actual, etc.
COMPETENCIES & SKILLS
- Empathy & Trauma-Informed Practice: Engages respectfully and compassionately with individuals and teams facing difficult realities, applying trauma-informed principles across all interactions.
- Supervisory Confidence: Comfortable holding accountability, providing direct feedback, and navigating the interpersonal complexity of managing a small, close-knit team in high-stress work.
- Adaptability & Resilience: Thrives in a dynamic environment, maintains composure under pressure, and adapts quickly to shifting priorities. This role involves regular proximity to distressing situations and requires someone who has developed healthy boundaries, strong coping strategies, and the capacity to support others through difficulty while sustaining their own well-being.
- Collaborative Problem-Solving: Works effectively across teams, service providers, and community stakeholders to find practical solutions and strengthen the program's impact.
- Community Presence: Brings visibility, credibility, and warmth to the role — someone who is recognized and welcomed in both the business community and the broader downtown environment.
OTHER ASSETS
- Certifications (CPR, First aid, Naloxone, etc.)
- Education or equivalent experience in a supervisory/management role
- Exposure to people who suffer from mental health and/or addictions challenges
- 3-5 years’ experience in a professional environment
- Understanding of software systems such as HIFIS
Benefits after 3-months include:
- Extended Health Care Insurance
- Employee Assistance Program
- Wellness Account
- Paid Holiday Time
- Casual dress
- Company events
- Employee RRSP Contribution
Pay: $50,000.00-$75,000.00 per year
Work Location: In person
