Leaves Specialist

Chicago Public Schools; Chicago (IL); On-site; USD 50,000 - 68,000; Full time

Benefits offered by this job

Health plan options

Vision

Retirement plans

Flexible Spending Accounts

Job summary

Chicago Public Schools is seeking a Leaves Specialist in the Absence & Disability Department to manage intake and processing of medical and non-medical leaves and the Short-Term Disability benefit, including communications and records maintenance with email and a Tier II call center.

Reporting to the Absence & Disability Manager, the role requires knowledge of FMLA, CPS policies, HIPAA compliance, and the ability to coordinate with Payroll, Benefits, and other CPS offices.

Qualifications

• Excellent customer service acumen; results-oriented and able to work well in a fast-paced team environment.
• Detail-oriented with strong communication, problem-solving, critical thinking, and interpersonal skills.
• Must be organized, self-starter able to log all completed activities.
• Demonstrate integrity and credibility in handling confidential information.

Responsibilities

• Provide tier 2 customer support regarding leave of absence benefits, insurance, short-term disability and entitlement information.
• Respond to employee inquiries by phone and email with timely and accurate responses.
• Organize, upload and monitor all leave-related information in inboxes.
• Develop knowledge of CPS leave policies, Short-Term Disability Plan and employment policies.
• Complete intake and processing for all leaves of absence in accordance with laws and CPS rules.

Skills

Customer service

Communication

Problem solving

Interpersonal skills

Education

High School diploma or GED

Bachelor’s degree

Tools

Google Suite

PeopleSoft

Oracle

Job description

Posting Date

Sep 15, 2026, 3:01:45 PM

Primary Location

West Side-2651 W Washington Blvd (Dodge-Garfield Park)

Estimated Annual Salary Range

50,000.00 - 67,500.00

Position Type : Non-Union Position

Overtime Status

Exempt

Final salary offers are dependent upon candidate qualifications.

JOB DESCRIPTION ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

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 Absence and Disability Department within the Talent Office is responsible for processing all medical and non-medical leaves of absence, administering the AWOL (absent without leave) process, Short-Term Disability, Benefit Billing, Donation of Sick Days, Fitness for Duty and Reasonable Suspicion exams.

Job Summary

Reporting to the Absence & Disability Manager, the Leaves Specialist is responsible for the intake and processing of all medical and non-medical leaves of absence and the Short-Term Disability benefit, including administration, mailings, communication, and records maintenance through email and a Tier II call center. The Leaves Specialist will be a knowledgeable resource in the areas of FMLA federal law, CPS supplemental medical leaves, non-medical leaves, and Short-Term Disability per CPS policy and Board rules. Additionally, this position will be a liaison between Workers Compensation, Benefits Billing, the ADA Office, the Office of Administrative Hearings, Payroll, CPS Staffing, and the Talent Office. This is a full-time, exempt position that will be paid for time worked on a salary basis.

Responsibilities

• Provide tier 2 customer support regarding leave of absence benefits, insurance, short-term disability and entitlement information
• Responsible for the service quality and efficiency of assigned transactions including responding timely and accurately to employee inquiries by phone and email
• Organize, upload and monitor all leave-related information in inboxes
• Develop a working knowledge of CPS leave policies, Short-Term Disability Plan and employment policies
• Complete intake and processing for all leaves of absence including FMLA, short-term disability, CPS supplemental leaves, paid parental leave, and non-medical leaves, in accordance with FMLA law, CPS Policy and Board Rules, CPS Short-Term Disability (STD) Plan, and Collective Bargaining Agreements
• Research and resolve employee inquiries about leaves of absence and discrepancies with pay from the STD benefit. Escalate STD appeals and FMLA second opinions. Collaborate with team members to respond timely to all questions and escalations.
• Review medical information per FMLA law, STD Plan, Board policy, and collective bargaining agreements. Familiarity with ODG and FMLA guidelines. Input ICD codes accurately.
• Serve as a liaison between the leave of absence program and other CPS departments, schools, and the HR Talent Partners. Provide advice and information on all aspects of the leave of absence and Short-Term Disability programs.
• Ensure HIPAA and ADA compliance and confidentiality of employee matters is maintained
• Other duties as assigned
  

Qualifications

Education Required

High School diploma or GED equivalent is required

Bachelor’s degree from an accredited college or university and a minimum of two (2) years of related experience, preferred

Experience Required

Minimum of five (5) years of relevant experience, including two (2) years of experience administering leaves of absence, healthcare, or Short-Term Disability

Experience administering absence and/or disability leaves and data in an HRIS system (E.g., Peoplesoft) or other applicable leave management system preferred

Experience in a complex, large-scale and fast-paced environment preferred

Knowledge, Skills, and Abilities

Excellent customer service acumen; results-oriented and able to work well in a fast-paced team environment

Detail-oriented with strong communication, problem-solving, critical thinking, and interpersonal skills

Must be an organized, self-starter that is able to log all completed activities

Demonstrate high levels of integrity, honesty, credibility, and the courage to make difficult yet necessary decisions

Strong leadership and team-building skills

Ability to quickly develop a strong working knowledge of CPS leave policies, Short-Term Disability Plan and employment policies

Ability to build collaborative relationships with a variety of constituent groups, including external partners, to ensure the entire system operates in the most effective manner possible to support schools and principals

Ability to define problems, understand reports and related data, and outline valid conclusions and action steps

Ability to quickly gain a working knowledge of Google Suite, PeopleSoft, Oracle, and other CPS systems

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
• 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:

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.

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