Work Based Learning Jobs in Chicago, IL (NOW HIRING)

Student Support, Coaching & Self-Advocacy

• Supervision & Behavioral Management: Supervise students in groups and individually, monitoring behavior to ensure alignment with programmatic expectations.

• Student Counseling: Counsel students on personal, social, behavioral, or academic issues affecting their educational progress.

• Person-Centered Planning: Ensure every student actively leads or participates in their own Individualized Education Program (IEP) transition meetings. Utilize assistive technology, visual choice boards or person-centered tools to provide a voice for students with limited or non-verbal communication.

• Goal Realism & Guidance: Manage complex dynamics where a student's post-secondary dream conflicts with parental wishes or current skill realities. Apply strategies like "failing safely" (e.g., career-testing, job shadowing and temporary classes) alongside stepping-stone goals to gently navigate reality without crushing student ambition.

Compliance, Data, & Transition Assessments

• Student Evaluations: Evaluate individual student abilities, interests and personality characteristics using tests, records, interviews and professional sources.

• Multi-Faceted Assessment: Administer age-appropriate formal and informal transition assessments evaluating independent living, travel/transit skills, and actual work behaviors to formulate compliant, measurable post-secondary goals.

• IDEA Compliance: Apply strong knowledge of Individualized Education Act (IDEA) transition mandates to draft audited, highly scrutinized goals and dynamically pivot plans based on assessment data.

• Rigorous Progress Tracking: Utilize robust organizational systems such as digital tracking tools, rubric-based feedback from job coaches, and student self-monitoring checklists to track and document progress when students are off-campus at work-based learning sites.

Collaboration, Networking & Program Development

• Community Site Development: Develop and maintain strong relationships with community sites, public transit systems, and external agencies.

• Work-Based Opportunities: Develop work-study programs, internships, and volunteer opportunities for students to gain competitive experience while completing their high school curriculum.

• Agency Connections: Manage the "Service Cliff" by facilitating warm handovers introducing families directly to agency contacts and connecting students with Vocational Rehabilitation (VR), Pre-Employment Transition Services (Pre-ETS), and developmental disability boards.

• Business Empathy & Partnerships: Proactively engage local business owners, pitching inclusive hiring benefits and demonstrating how a transitioning student adds tangible value to their workforce.

Workplace Intervention & Crisis Management

• Workplace Learning Labs: Safely intervene when work-based placements experience friction, behavioral incidents, or employer misunderstandings.

• Student Independence Coaching: Use workplace mistakes as a live curriculum, coaching students on how to navigate portals, look up records, request legal accommodations,and repair professional relationships independently rather than filling out paperwork for them.

• Education: Bachelor's Degree strongly preferred.

• Background in education or social work preferred.

• Regulatory Knowledge: Demonstrate deep, compliance-centered knowledge of transitioning students as per the Individuals with Disabilities Education Act (IDEA) mandates.

• Transition & Coaching Experience: Documented knowledge and/or experience placing and coaching students in jobs, as well as assisting them in transitioning to college, career, and independent life.

• Systemic Mindset: Demonstrated ability to constantly focus on the "real world," utilizing community agency networks, public transit routes, and outer-community resources.

• Behavioral & Performance Knowledge: Knowledge of human behavior, performance, and specific student needs (e.g., Autism Spectrum Disorder, ADHD).

• Professional Soft Skills: High level of professionalism, strong decision-making skills, and the ability to communicate calmly, transparently, and effectively in writing across varied audiences, including resistant families, school teams, and litigious stakeholders.

This job description is not intended to be all-inclusive, and the employee shall perform other reasonably related school duties as assigned by administrators.  This organization reserves the right to revise or change job duties and responsibilities as the need arises. This job description does not constitute a written or implied contract of employment.