My Way Out – Now Hiring Reentry Support Partner

April 19, 2023
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Position: Reentry Support Partner / Limited Term Employee (could be extended depending upon mutual fit, ongoing program needs and programming funding)

Our Company:

My Way Out, Inc
Apply: Send Resume to [email protected]


Our Mission:

To empower and enrich the lives of justice-impacted individuals, by bringing together community resources, supportive service providers, and employers. By reducing recidivism, building strong communities, and keeping families together, we will help bring hope and prosperity to marginalized communities.


A Reentry Support Partner (RSP) conducts the same duties as a case manager, but here at My Way Out (MWO), we understand that words have power. Our RSP will listen to how our justice impacted clients view their own Way Out, and will work together with them to create a personalized reentry plan. The RSP will provide personalized guidance and resources including supportive services, employment & training opportunities, and ongoing educational opportunities available to justice- involved individuals. The RSP will work together with the client to help them stay on track with their personalized reentry plan, while also maintaining case notes and updates of every client’s journey in our CMS system and mobile app.

DEPARTMENT: Operations

LOCATION: Milwaukee, WI



Part-Time (20 Hrs. a week)

WORKPLACE TYPE: Remote / Onsite

REPORTING TO: Executive Director

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Manages a caseload of participants and provides counseling and mentoring

Assesses participant competencies, work history, educational attainment, skills and abilities; identifies challenges to finding employment and prompts them to find solutions

Conducts individual meetings/follow-ups with participants for supportive services, job search, education, job retention, and/or job readiness

Completes an individualized overview of available services and works with participant to create an individualized personal reentry plan for short- and long-term goals

Maintains information about area resources and employers

Ensures participant accountability and attendance; tracks and maintains employment retention goals

Provides information to participants on available training and/or jobs that will lead to advancement


Assumes central responsibility for participants achieving self-sufficiency by monitoring progress throughs self-learning mobile app.

Prepares, organizes, and maintains accurate, updated information in confidential electronic files reflecting the entire history of a program participant including a log of supportive services provided

Leverages case management support with a focus on helping justice-involved to prepare for employment that leads to self-sufficiency


A combination of education and training equivalent to the qualifications as stated will be considered.

Encouraged to apply if you have lived life experience and are a justice impacted individual (***Due to partnerships and state and federal grants requirements, we are seeking individuals that are no longer on probation or parole)

Minimum of related Associate Degree from an accredited university or college, or equivalent work experience in responsibilities of position

Excellent verbal and written communication skills

Knowledgeable in Microsoft Word, Excel, and Windows, and Google Drive

Willing to learn other platforms and technology

Demonstrated customer service skills

Familiarity with the communities being served, with knowledge and understanding of local needs and resources

One to three years’ experience in workforce development or related programs preferred

Valid Driver’s License and transportation