Transition Specialist

Chicago Public Schools (CPS) is a district on the rise, serving over 325,000 students in 500+ schools and employing over 45,000 people, most of them teachers. CPS has set ambitious goals to ensure that every student, in every school and every neighborhood, has access to a world-class learning experience that prepares each for success in college, career, and civic life. Aligned with our transformed philosophy, we are steadfastly focused on ensuring that the District provides resources equitably to support every student, every school, and every community. Six core values guide the work we do every day for our students – student-centered, whole child, equity, academic excellence, community partnership, and continuous learning. Each role in the district supports our vision that every student deserves a rigorous, joyful, and equitable learning experience.

The Office for Student with Disabilities is responsible for student evaluations, creating and monitoring Individualized Education Programs (IEPs), and working with schools, staff, and families to fulfill these plans toward greater student development and achievement. OSD uses a data-driven approach to best support the needs of each individual student and does so in compliance with federal and state regulations regarding special education, including the Individuals with Disabilities Education Act (IDEA) and Section 504 of the Rehabilitation Act of 1973.

Job Summary

Reporting to the Director of Academic Access, the Transition Specialist will be responsible for supporting the implementation, expansion and monitoring the successful execution of transition services for students with disabilities, including but not limited to planning for transition to post-secondary independence and designing thoughtful transitions between grades. The Transition Specialist will implement coordinated activities to support students with disabilities in their transition to successful outcomes in post-secondary employment, education, training, independent living, and community involvement through collaboration with school personnel, students, families, community partners, post-school service providers, governmental agencies, and employers. This is a full-time, exempt position that will be paid for hours worked on a salary basis.

The Transition Specialist will be held accountable for the following responsibilities:

• Vital administrative tasks that directly support our students and connects them to an agency
• Facilitate the intake of DRS referrals
• Oversee the upkeep of our applicant data tracker to ensure comprehensive record-keeping
• Adhere to required yearly application numbers set by DHS
• Collaborate with DHS counselors and personnel to ensure effective support for the DRS process
• Provide essential guidance to families and students on how to connect with DHS and begin their DRS referral journey
• Support schools through providing guidance, technical assistance, and leading professional development sessions for school staff in areas including but not limited to:
• Maintain a focus on inclusive practices
• Promote increased awareness and accessibility to district-wide programs and/or services encouraging participation in activities supporting the three areas of transition: post-secondary employment, post-secondary education and/or training, and independent living skills training
• Support schools in the effective implementation and facilitation of structures promoting student, school and family involvement with agencies, their events, and services available
• Participate in the implementation of post-secondary-related grants, including accurate data collection, providing information to students, families, and school staff regarding new transition opportunities, and sharing relevant information across OSD in support of future grant opportunities
• Collaborate with Transition team colleagues in planning activities and events to increase post-secondary options for students such as career fairs, transition fairs, high school fairs, and job shadow days; recruit and support participants in the successful execution of these events
• Collaborate with community partners, including city and state agencies, community agencies, post-school service providers, university partners, and other organizations to identify new or additional school and community-based transition supports that may benefit CPS students
• Ensure students, families and school personnel are provided with ongoing access to accurate, relevant resources and information regarding topics such as community living, employment and post-secondary education/training. Support schools in the effective implementation and facilitation of structures promoting student, school and family involvement in agency support and services
• Support schools in work on state-level monitoring, completion of required audits, and all aspects of compliance with ISBE indicators 13 and 14:

Collect data for audits, review of post-school activities, and submission of compiled information to ISBE upon completion

Assist school staff with remediating or correcting transition plans and IEPs to bring them into compliance with the ISBE rubric

Support schools selected for audits in contacting students 1-year post-graduation to conduct surveys, obtain and record information regarding their current activities surrounding post-secondary education, employment and independent living

• Promote increased awareness and accessibility to district-wide programs and/or services encourage participation in activities supporting the three areas of transition: post-secondary employment, post-secondary education and/or training, and independent living skills training
• Other duties as assigned

In order to be successful and achieve the above responsibilities, the Transition Specialist must possess the following qualifications:

Education Required

• Bachelor’s degree in Education, Rehabilitation Services, Counseling, or related field from an accredited college or university, required
• Valid teaching certificate/Professional Educator’s License (PEL) issued by the Illinois State Board of Education (ISBE) with LBSI and LBS-II Transition Specialist endorsements, preferred
• Master’s degree in Transition Special Education or Rehabilitation Counseling and/or related graduate certification, preferred

Experience Required

• Minimum of three (3) years educational work and/or social service experience is required
• Experience working with students with disabilities is preferred
• Extensive experience in developing and delivering professional training related to school-to-career initiatives, comprehensive support processes, special education issues, and/or teaching and learning

Other Requirements

• Bilingual fluency in English and Spanish, and/or American Sign Language, preferred

Knowledge, Skills, And Abilities

• Strong knowledge of regulations and procedures stipulated in IDEA, with emphasis on transition planning and IEP compliance
• Knowledge of regulations and procedures stipulated in ADA with emphasis on Section 504 and high school to college differences
• Knowledge of vocational and other transition assessment techniques
• Knowledge of strategies for developing, coordinating, and maintaining community-based work training programs
• Knowledge of federal, state, and local child labor laws
• Excellent verbal and written communication skills
• Ability to build collaborative relationships and work effectively with a variety of constituent groups from diverse backgrounds, including both internal and external stakeholders and agencies, students, parents, and school staff, to cultivate an atmosphere of cultural responsiveness, respect, and teamwork
• Capable of promoting and encouraging parental involvement and participation in the transition process
• Ability to define problems, analyze data, and outline valid conclusions and action steps; capable of utilizing various software programs and data tracking systems for project and program efficiency

Benefits

Health & Wellness: Your Care, Your Choice

CPS Is Committed To Providing Comprehensive Health Coverage To Our Employees And Their Eligible Dependents. You'll Have Access To a Variety Of Choices To Best Fit Your Needs

Medical Plan Options

Pharmacy

Dental

Vision

Behavioral Health & EAP

Employee Wellness Program

Financial Security: Planning for Today and Tomorrow

We understand the importance of financial stability, which is why CPS offers strong retirement and savings options:

Basic Life Insurance

Life and Disability Insurance

Pension Plans

Supplemental Retirement Plans (403(b) and 457(b))

Flexible Spending Accounts (FSAs)

Spot Pet Insurance

Work-Life Balance: Supporting Your Personal and Professional Life

CPS values the well-being of its employees and offers competitive paid time off policies:

Paid Leave

Sick Leave

Vacation Days

Parental Leaves

Short-Term Disability

Religious Holidays

Leaves

Reference the Chicago Public Schools: A Comprehensive Benefits Overview or the benefits handbook for comprehensive details.

Conditions of Employment

As a condition of employment with the Chicago Public Schools (CPS), employees are required to:

• Establish/Maintain Chicago Residency - Employees are required to live within the geographic boundaries of the City of Chicago within six months of their CPS hire date and maintain residency throughout their employment with the district. The Chicago residency requirement does not apply to temporary/part-time positions; however, all CPS employees must be residents of Illinois.

Posting Date

Aug 12, 2026, 11:28:35 AM

Primary Location

Central-42 West Madison Street (Ofc Students w/Disab-Inst Supp)

CPS Non-Union Job Grade

S06

Estimated Annual Salary Range

54,000.00

Position Type

Non-Union Position

Overtime Status

Exempt