CTA Outreach Supervisor

The CTA Outreach Supervisor leads The Night Ministry's CTA-based outreach program, currently operating Wednesday and Thursday nights, and is responsible for the safety, quality, and consistency of services delivered to people experiencing homelessness in CTA transit locations. This role builds trust with clients through a trauma-informed, risk reduction approach, supervises outreach staff in the field, and ensures the program runs smoothly from night-of logistics through funder reporting.

Outside of scheduled CTA outreach shifts, the Supervisor completes program administration, staff supervision, data review, partner coordination, client follow-up, outreach, and operational support across OHM as assigned.

• Oversee all operations of the CTA Outreach Program, including staffing, planning, site coordination, shift execution, follow-up, documentation, and continuous program improvement
• Develop and maintain standard CTA outreach workflows, including shift preparation, field roles, safety response, client follow-up, documentation, and post-shift closeout
• Act as team leader in the field, directing outreach activities and adjusting plans as conditions change
• Carry out periodic community needs assessments to inform program direction
• Supervise CTA outreach staff as applicable, including regular bi-weekly supervision and bi-annual performance evaluations; approve timesheets and time-off requests within 48 hours of submission
• Support recruitment, hiring, onboarding, and ongoing coaching of outreach staff and interns
• Serve as a liaison to volunteers and organizational partners, providing orientation and building relationships that encourage community involvement
• Serve as the primary point of contact for safety issues during outreach, assessing risk and re-routing the team as needed
• Provide crisis intervention and de-escalation support
• Build rapport with clients using motivational interviewing, risk reduction, and trauma-informed practices, and connect them to services and referrals
• Coordinate supply provision, keeping outreach inventory stocked, organized, and accessible
• Coordinate vehicle logistics, including scheduling and driving the outreach van as needed
• Monitor program performance, review data quality and outcomes, and prepare accurate and timely grant reports, program updates, and supporting documentation
• Attend grant-related meetings as the programmatic liaison for the CTA program
• Support other outreach programs within OHM
• Support client follow-up visits in coordination with other team members
• Stay current on issues affecting the target population, including relevant literature, resources, and street dynamics
• Attend staff, agency, and inter-agency meetings, and participate in training opportunities as required
• Occasionally represent The Night Ministry at community events and public relations or fundraising activities
• Complete special projects and other duties as assigned

• BA degree from an accredited college or university
• Demonstrated experience in crisis intervention and de-escalation
• Comfortable working in all Chicago neighborhoods
• Excellent interpersonal and organizational skills
• Valid driver's license, evidence of insurability, and willingness to drive the Outreach Van
• Physically able to be outdoors and mobile for up to six consecutive hours in all Chicago weather conditions
• Flexible schedule to accommodate early morning, evening, and weekend hours

• Spanish language proficiency

The physical demands and work environment described here are representative of those an employee must meet to perform the essential functions of this role. Reasonable accommodations may be made for individuals with disabilities.

• Occasionally required to stand, walk, sit, use hands, climb stairs, crouch, or crawl, and to talk, hear, taste, or smell
• Occasionally required to lift and/or move up to 50 pounds, and to drive an automobile or the outreach van
• Vision requirements include close vision, distance vision, color vision, peripheral vision, depth perception, and the ability to adjust focus
• Exposure to all varieties of Chicago weather, with work occurring during daytime and evening or late-night hours

Women, people of color, LGBTQ individuals, and those with lived experience of homelessness are encouraged to apply.

Employees are expected to adhere to all organizational policies and regulations specified by the State of Illinois and The Night Ministry.