Executive Director, Service Delivery

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 Students with Disabilities (OSD) works to support networks, schools, and families with all issues related to special education including instruction, interventions, and legal and compliance support. OSD provides the tools and resources to ensure that all diverse learners receive a high-quality public education that prepares students for success. Diverse Learners in our district refers to students with Individualized Education Programs (IEPs) and 504 Plans. OSD supports networks, schools, and families with all issues related to special education, including instruction, interventions, and legal and compliance support.

Job Summary

Reporting to the Chief of the Office for Students with Disabilities, the Executive Director of OSD Service Delivery assists in the targeted planning and implementation of the department’s strategic plan to increase high-quality standards in instruction and improve outcomes in schools for students with disabilities. The Executive Director of OSD Service Delivery serves as a member of the Office for Students with Disabilities leadership team and ensures consistent implementation of practices and guides the District’s vision for special education. This is a full-time, exempt position that will be paid for time worked on a salary basis.

The Executive Director of OSD Service Delivery will be held accountable for the following responsibilities:

• Leads the strategy, continuous improvement, and operations of the Service Delivery department
• Leads and supports the Service delivery team, functions, and operations, including but not limited to the areas of Vision Impairment, Deaf & Hard of Hearing, Home Hospital, Assistive Technology, Translation Service, and School Assignment to ensure the respective areas are following District policies and practices, and special education law, policies, and best practices
• Ensures compliance with all local, state, and/or federal guidelines and policies as they relate to screening and assessing eligibility for specialized services and/or assignment to specialized placements, per the students’ Individualized Education Program (IEP)
• Ensures the respective areas they support are following special education law and policies as well as best practices
• Monitors and helps report adherence to all compulsory rules and regulations
• Supervises, develops, and manages the performance of a high-functioning, collaborative team of professionals including managers responsible for articulating clear, research-based approaches in Service Delivery; Coordinates, plans, implements, and evaluates training and professional growth experiences for assigned staff
• Assists OSD Senior Leadership team in their comprehensive assessment of needed areas regarding the development of compliant and data-driven IEPs on behalf of students with disabilities
• Investigates and submits written responses to ISBE regarding State Performance Plan indicator findings and supports corrective action plans that might be ordered by ISBE pursuant to these monitoring processes
• Designs, develops, and manages processes and procedures in collaboration with content leads within OSD and with other District offices
• Collects and analyzes process and outcome data to continually gauge effectiveness and improve performance
• Collects and communicates key performance indicators with The Chief, Deputies,
• colleagues, school officials, board members, and the public as appropriate
• Builds the capacity of district staff to effectively address issues related to services for students with disabilities including the resolution of parent concerns
• Measures and evaluates school implementation and provides data and feedback to district administration and OSD senior leadership on an ongoing basis
• Other duties as assigned
  

Education Required

In order to be successful and achieve the above responsibilities, the Executive Director of OSD Service Delivery must possess the following qualifications:

• Master's degree in a relevant educational field from an accredited college or university, required
• A valid Professional Education License (PEL) issued by the Illinois State Board of Education (ISBE), required
• Principal endorsement/valid State of Illinois General Administrative Certificate, strongly preferred
  
  

Experience Required

• Minimum eight (8) years of experience in district leadership, case management or similar roles supporting diverse learners
• Minimum five (5) years of supervisory experience
• Principal experience strongly preferred
  
  

Knowledge, Skills, And Abilities

• Strong leadership, team building and communication skills (speaking, writing, and listening) that create a team culture of high expectations and accountability for achieving results that are timely, accurate, and complete
• Fosters trust and collaboration by seeking input and buy-in from stakeholders; builds and maintains strong relationships internally and externally
• Strong leadership development and coaching ability to provide continual training for the team
• Can establish clear, well-defined structures for monitoring progress toward desired outcomes
• Ability to effectively lead a team of technically-skilled employees in an educational setting
• Ability to manage professionals, review work effectiveness, and develop colleagues’ skills as needed
• Collaboration skills to work effectively with a wide range of district personnel, families, and the general public
• Demonstrated ability to design and implement short and long term objectives
• Ability to effectively lead, organize, and direct the work of others
• Strong decision-making ability and resource management skills
• Strong analytical and problem-solving skills
• Excellent skills in data collection and analysis, interpretation, report writing, and presentations
• Knowledge of research and evaluation methodologies
• Knowledge of data systems including enterprise data warehouses and student information systems
• Ability to handle multiple concurrent activities, work under pressure, and prioritize work effectively to meet deadlines
• Proven ability to make recommendations on various topics, detailed, controversial, simple or complex
• Ability to be flexible and adapt as needed between in-person, virtual, and hybrid environments
• Capable of managing large, high-priority projects and programs within a large, complex organization
• Ability to quickly learn and effectively apply district policies and procedures
  
  

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.
  
  

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.

Posting Date

Oct 2, 2025, 3:50:13 PM

Primary Location

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

CPS Non-Union Job Grade

S11

Estimated Annual Salary Range

115,000.00

Position Type

Non-Union Position

Overtime Status

Exempt