Career Planner - 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 Career Planner provides career coaching, employment services, and case management to justice-involved individuals as they prepare for release from incarceration and transition back into the community. This position works with participants before and after release to develop employment and career plans, build job readiness skills, connect with education, training, and supportive resources, and obtain and retain meaningful employment. Working in partnership with the Wisconsin Department of Corrections, employers, workforce partners, and community organizations, the Career Planner helps participants build successful pathways to employment and community reintegration.

Position Details

• Reports To: Director of Operations
• Classification: Full-Time | Non-Exempt
• Work Location: Assigned Jackson Correctional Institution or New Lisbon Correctional Institution Regular travel throughout the region may be required.
• Compensation: $49,920–$59,259 annually ($24.00–$28.49/hour), depending on qualifications and experience, in accordance with WCI's Board-approved Pay Plan.
• Benefits: WCI offers a comprehensive benefits package, including health, dental, vision, life, and disability insurance; employer-supported health reimbursement benefits; paid holidays; generous paid leave; and professional development opportunities. Eligibility requirements apply.
  
  
  

Primary Responsibilities

• Provide employment-focused case management and career coaching to Windows to Work participants before and after release from incarceration.
• Assess participant strengths, barriers, employment readiness, and career goals and develop individualized employment and career plans.
• Provide job readiness assistance, including résumé development, interviewing, workplace readiness, career exploration, and job search support.
• Connect participants with employment, education, occupational training, apprenticeships, supportive services, and community resources.
• Build relationships with employers, including those committed to second-chance hiring, and identify employment opportunities that align with participant skills and goals.
• Coordinate services with correctional staff, probation and parole agents, employers, workforce partners, and community organizations.
• Maintain accurate participant records and required program documentation while ensuring 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.