Homeless Outreach Specialist

POSITION TITLE: Homeless Outreach Specialist (full-time, salaried)
REPORTING TO: Executive Director
SALARY: $52,000/year; benefits include paid holidays, paid time off, health, dental, and vision insurance, and more!

Deadline to Apply: May 14th, 2025 – Noon
Initial Screening: May 15th and 16th
First Interview: May 22nd and 23rd
Second Interview: May 27th
Decision Date: May 30th
Approximate Start Date: June 13th
How to apply: Send a resume AND cover letter to office@madisonstreetmedicine.org.

If a cover letter is not included you will not be considered for the position.


Summary:
The Homeless Outreach Specialist works with an interdisciplinary team of staff and volunteers to provide housing services for Madison Street Medicine programs dedicated to filling gaps in access to healthcare and housing in the Madison Area. They focus on outreach to individuals living unsheltered in Madison—on the streets, in tents, vehicles or other places not meant for human habitation. You’ll distribute essential supplies, build relationships grounded in trust, and support clients through finding housing, care coordination, and connection to healthcare and other services.

We’re looking for someone who’s passionate about housing justice, trauma-informed in their approach, and comfortable with a strong harm reduction approach. Experience in homeless services, lived experience in houselessness or bilingual in Spanish is especially valued. If you’re organized, adaptable, able to work independently and ready to support clients through complex challenges, this is your chance to make a tangible impact in our community and we’d love to hear from you.


GENERAL RESPONSIBILITIES

  • Outreach: Perform weekday outreach to places where unsheltered homeless individuals reside providing basic survival gear and other supplies. Serve as a resource for unsheltered individuals to meet needs.
  • Engagement: Once a relationship is developed through outreach, engage with individuals about goals and needs while providing information about community resources.
  • Housing Search & Placement: Assist interested individuals in getting connected to Coordinated Entry as well as perform other housing search and placement tasks.
  • Case Management and Care Coordination: Using a client-centered approach, assist in coordinating medical and housing related appointments and associated paperwork and data entry. Assist in connecting clients to appropriate services based on their needs.
  • General Expectations: Be a dependable team player aligned with Madison Street Medicine’s vision, mission and values including respectful and compassionate interactions with people experiencing homelessness and maintaining client confidentiality. Maintain a positive attitude, exercise good communication skills, meet deadlines, follow personnel policies, attend required staff meetings, one-on-ones and trainings and use technology provided by the organization. Actively participate in sociocratic circles as assigned.

SPECIFIC JOB DUTIES INCLUDE:

  • Proactive weekday, daily outreach and engagement activities to various places people experiencing homelessness reside (street, woods, parking lots, etc) providing basic supplies and information and referrals.
  • Monitoring housing priority lists and opportunities to connect clients with housing opportunities, including chronic homelessness documentation, assistance connecting with other service providers and landlords.
  • Timely data entry and updates to the Dane County Homeless Management Information System (HMIS) for Madison Street Medicine program participants, including completing monthly interim assessments and entry/exits from the program.
  • Ensuring confidentiality for our clients, including obtaining releases of information and providing information about rights and responsibilities related to the data of program participants.
  • Attend Homeless Services Consortium Outreach and Case Conferencing meetings and report back to staff and volunteers as needed.
  • Assist in educating Madison Street Medicine volunteers and staff housing matters.
  • Assist in connecting clients to other housing and mainstream resources, as needed.
  • Provide case management and care coordination for clients enrolled in our programs.
  • Other duties as assigned.

SKILLS AND QUALIFICATIONS:

  • A passion for ending homelessness and working with people without homes.
  • Ability to be trained in HMIS and maintain required certifications.
  • Ability to be trained in Madison Street Medicine Electronic Health Records system.
  • Commitment to maintaining confidentiality of our program participants.
  • Ability to interact with clients in a trauma-informed way that includes harm reduction and centers on the program participants needs.
  • Ability to meet clients where they are at and be flexible in providing services.
  • History of positive working relationships with people of diverse racial/ethnic, socio-economic, and educational backgrounds.
  • Demonstrated ability to use creative problem-solving skills to assist persons of diverse backgrounds and abilities, often in extreme personal crisis.
  • Good organizational skills and ability to work independently and with close attention to details.
  • Ability to learn about government or social services agencies that assist people without homes.
  • Commitment to the mission of a small, volunteer driven non-profit organization.
  • Ability to have a flexible schedule.
  • Use of personal vehicle for doing outreach (mileage reimbursed).
  • Lived experience of homelessness, experience in the homeless services system in Dane County, bilingual in Spanish or ASL a plus.

If you feel that you are a good fit, please apply by sending your resume AND a cover letter to office@madisonstreetmedicine.org or by applying below.

Apply for this position

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