Employment Specialist

Job Number:

260002HI

Posting Date

: Oct 2, 2026, 1:04:16 PM

Primary Location

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

CPS Non-Union Job Grade: S05

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.

Substitute Services administers four substitute pools totaling 7,914 employees, including payroll processing, benefit day approvals, and incentive and PD payments. The department also oversees seven retention pools with more than 850 enrolled employees and manages their school assignments and payroll. In addition, Sub Services manages the Frontline automated sub placement system for over 25,000 full‑time employees and handles rehires, cadre staffing, discipline cases, handbook updates, and the sub exclusion processes. The team also supports daily assignments for citywide cadres, ODLSS and ADA coverage, and long‑term ESP placements. This work ensures consistent daily coverage, operational continuity, and compliance across all substitute and retention groups districtwide.

Job Summary:

Reporting to the Manager of Substitute Services, the Employment Specialist supports Core Cadre staffing and daily districtwide coverage by coordinating Core Cadre assignments and payroll, managing citywide daily assignments, and monitoring incentive payments. The position works closely with Network Chiefs to assign Core Cadre to schools requiring additional support. This role will build positive relationships with substitutes and school leaders to ensure the district is maximizing all resources to cover absences, resulting in higher fill rates. This is a full-time, exempt position that will be paid for time worked on a salary basis.

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

• Manage daily placement of CORE cadres and their payroll
• Generate reports from Substitute Services’ automated sub placement system (Frontline)
• Submit sub teacher tier payments in the Supplemental Payroll System (SPS)
• Research and verify all tier payment inquiries in a timely manner
• Assign citywide cadres to daily assignments
• Troubleshoot Frontline issues as they arise
• Provide customer service support via email, in-house, and telephone
• Perform other duties as they might be assigned

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

Education Required:

• High school diploma or GED equivalent required
• Bachelor’s degree from an accredited college or university preferred

Experience Required:

• Minimum of three (3) years of experience with payroll systems required
• Experience with CPS-specific payroll systems (Kronos, SPS) highly preferred
• Five (5) years of customer service experience preferred

Knowledge, Skills, and Abilities:

• Willingness to work collaboratively with others to achieve district and/or departmental goals and objectives.
• Ability to manage and prioritize a variety of tasks/responsibilities in a timely and efficient manner.
• Communicates effectively through various media and articulates industry terminology in an easily understood manner.
• Proven track record of thoroughness and follow-through on projects and daily tasks.
• Excellent customer service skills with an ability to empathize and be attentive to customers’ needs and concerns.
• Strong team-building skills (e.g., ability to work with high-performing teams united around a clear vision for serving schools and achieving student success)
• Strong technology skills in Microsoft Office Suite, Google, Kronos, SPS, and applicant tracking systems.
• Readiness to work extended hours when necessary along with flexibility to adapt to changing timelines.

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.