Reentry Coordinator - Windows to Work

About Workforce Connections

At Workforce Connections, Inc. (WCI), we believe that meaningful work changes lives. As a nonprofit organization dedicated to connecting people, work, and training, we provide innovative workforce development, family support, education, and community-based services that empower individuals, strengthen families, support employers, and build thriving communities. Every member of our team plays an important role in creating opportunities, removing barriers, and helping people discover their purpose, passion, and potential.

Position Summary

The Windows to Work Reentry Career Planner helps individuals prepare for a successful transition from incarceration back into their communities, with a strong emphasis on employment, stability, and long-term success. Working with individuals before and after release, this position provides individualized reentry planning, case management, career coaching, and connections to community resources that address barriers to successful reintegration. Working in partnership with the Wisconsin Department of Corrections, probation and parole agents, employers, workforce development partners, and community organizations, the Reentry Career Planner helps participants navigate the challenges of returning to the community, develop realistic employment goals, access essential resources, and build a foundation for lasting independence.

Primary Responsibilities

• Provide individualized reentry case management and transition planning to individuals preparing for release from incarceration and returning to their communities.
• Assess participant strengths, needs, barriers, and readiness for reentry, and develop individualized plans that support employment, stability, and successful community reintegration.
• Help participants identify and address barriers to successful reentry, including employment, housing, transportation, identification, education, and access to community-based support services.
• Provide career coaching, job readiness training, résumé development, interview preparation, job search assistance, and employment retention support.
• Build relationships with employers, including second-chance employers, to identify employment and training opportunities for individuals returning from incarceration.
• Coordinate with correctional institution staff, probation and parole agents, workforce partners, and community organizations to support continuity of services before and after release.
• Maintain accurate participant records, document services and progress, and ensure compliance with Windows to Work, Department of Corrections, and organizational requirements.

Qualifications

Education & Experience

• Associate degree in human services, criminal justice, social work, education, workforce development, or a related field and relevant experience required. Bachelor's degree or additional related experience preferred.
• Experience in case management, workforce development, career coaching, social services, corrections, reentry services, education, employment services, or a related field preferred.

Knowledge & Skills

• Strong communication, coaching, relationship-building, organizational, documentation, and problem-solving skills.
• Ability to work effectively with individuals experiencing multiple barriers to employment and build positive, professional relationships.
• Knowledge of employment readiness, career development, community resources, and supportive service systems.
• Ability to collaborate effectively with correctional staff, employers, workforce partners, and community organizations.

Technology

• Proficiency with Microsoft Office, databases, and case management systems and the ability to learn Windows to Work, Department of Corrections, and other program-specific applications.

Other Requirements

• Must successfully complete required Department of Corrections and Windows to Work onboarding and training and maintain required system access and security credentials.
• Ability to maintain confidentiality, comply with correctional facility security and professional standards, exercise sound judgment, and travel as required.

Why Join Workforce Connections?

At Workforce Connections, our work changes lives. Every day, our team helps people overcome barriers, build employment and financial stability, and create new opportunities for themselves and their families. As a Windows to Work Career Planner, you'll have the opportunity to help individuals prepare for a successful return to their communities and build a new future through meaningful employment.

If you're passionate about workforce development, second chances, and helping people create lasting change, we'd love to hear from you. Workforce Connections, Inc. is an Equal Opportunity Employer.

Applications will be reviewed beginning November 16, 2026. The position will remain open until filled. Interested applicants are encouraged to apply early.