ABOUT US
Ascend Housing Services is a Wisconsin Medicaid 1915(i) certified Housing Support Services agency based in Madison. We help unsheltered adults in Dane County find and keep stable housing through hands-on, community-based field support. Our services are fully funded through Wisconsin Medicaid — no cost to the people we serve.
THE ROLE
You will carry a caseload of 6–10 members and work with them directly in the community — helping with housing searches, rental applications, landlord outreach, move-in coordination, and ongoing stability check-ins after they are housed. You meet members where they are: at shelters, apartment viewings, landlord offices, and community locations across Dane County.
This is independent, flexible, field-based work. You set your own schedule. You will not be in an office. You will be in the community building real relationships and producing real outcomes for people who need consistent, trusted support.
DETAILS
Type: Independent contractor (1099) — not an employee
Pay: $21.00 per hour, paid weekly
Hours: 15–20 hours per week, flexible scheduling
Location: Community-based across Dane County — no office required
Caseload: 6–10 members
Start date: Immediate
As a 1099 contractor you set your own schedule, manage your own taxes, and use your own vehicle and phone. No employer-provided benefits or paid time off.
WHAT YOU WILL DO
Search for available housing units that match member needs and budget
Contact landlords by phone, email, and in person on behalf of members
Accompany members to apartment viewings and help evaluate options
Assist with rental applications and gather required documents
Coordinate move-in logistics and support the transition into housing
Conduct stability visits with recently housed members
Respond to housing crises — eviction threats, landlord conflicts, lease issues
Connect members to community resources including benefits, healthcare, and employment
Document sessions the same day using a mobile app
Communicate daily with agency administrator
WHO WE ARE LOOKING FOR
We are not looking for a perfect resume. We are looking for people who show up reliably, communicate proactively, and care deeply about the people we serve.
Required:
Reliable transportation in Dane County and valid driver's license
Smartphone capable of running a mobile documentation app
Ability to work independently without daily in-person supervision
Ability to pass a Wisconsin caregiver background check
High school diploma or GED
Strongly preferred:
- Certified Peer Specialist (CPS) certification
- Lived experience of homelessness, housing instability, mental health challenges, or substance use recovery — this is valued, not disqualifying
- Experience in peer support, outreach, case management, shelter work, or social services
- Knowledge of Dane County housing resources and community organizations
Bilingual in Spanish, Hmong, Somali, or another language
THIS ROLE IS A GOOD FIT IF YOU:
- Show up when scheduled, every time, without being chased
Communicate proactively — if something comes up, you reach out before the session, not after
- Complete documentation the same day, not the next day
- Are comfortable working independently without a supervisor physically present
- Are passionate about housing justice and the population we serve
This role is NOT a good fit if you:
- Need daily reminders to complete tasks or show up to appointments
- Treat documentation as optional or something to catch up on later
- Are looking for a flexible gig you may deprioritize when life gets busy
- Are not comfortable working with people experiencing homelessness, addiction, or mental health challenges
HOW WE WORK
Every session is documented the same day using a mobile app. GPS is recorded at session start and end — this is a Medicaid compliance requirement. Payment is weekly and based only on approved, documented sessions. Sessions without completed documentation are not paid until documentation is submitted and approved.
You will send a brief check-in text before and after each session. You will be available for a weekly 15-minute check-in call. If you need to cancel a session, you notify the administrator and the member at least 2 hours in advance.
We do not micromanage people who are doing the job. We move quickly when someone is not.
APPLICATION PROCESS
Submit your application below
Complete applications are reviewed within 3 business days. Qualified applicants are invited to a 20-minute phone screen followed by an interview.
QUESTIONS? Email info@ascendhousingservices.org | Call 608-284-1335 | ascendhousingservices.org
Ascend Housing Services is committed to building a team that reflects the communities we serve. We strongly encourage applications from individuals with lived experience of homelessness, mental health challenges, substance use recovery, and other marginalized identities. We do not discriminate on the basis of race, color, religion, sex, national origin, age, disability, sexual orientation, gender identity, or background.