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Enterprise Technology Support Engagement Specialist

Chicago Public Schools
Chicago, IL Full Time
POSTED ON 7/10/2026
AVAILABLE BEFORE 9/7/2026
Enterprise Technology Support Engagement Specialist
Job Number: 250002F1
Posting Date: Jul 24, 2025, 2:51:57 PM
Primary Location: Southwest Side-501 W 35th St (Bridgeport)
CPS Non-Union Job Grade: S07
Estimated Annual Salary Range : 66,000.00 - 87,500.00
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 Department of Information and Technology Services (ITS) works to build the capacity of schools to use information and technology, maintain network infrastructure, security standards, and support other departments to meet district goals. ITS provides innovative technology solutions that improve the quality of education for students, reduce the administrative burden on educators, facilitate parent interaction, increase community engagement, and support CPS’ mission of transparency by focusing on the ease and equity of access to information.


Job Summary:

Reporting to the Enterprise Technology Support (ETS) Engagement Specialist Team Lead, the ETS Engagement Specialist will partner with applicable ITS, Central Office, Schools, and Strategic Vendors to support the I Innovate CPSTM Program, a professional development/training program, with the goal of advancing the use of technology within CPS classrooms (and other like programs as needed). The ETS Engagement Specialist will provide teachers with support ranging from one-on-one instructional support to team, grade-level, and whole-school professional development planning and facilitation regarding technology usage. The ETS Engagement Specialist will also serve as a School Customer Liaison between ITS and Schools.

The ETS Engagement Specialist will be held accountable for the following responsibilities:

  • Assist End Users in a variety of ways in order to optimize the educational return on the district’s investment of devices and related software tools and apps. Assistance includes teleconferences, webinars, screencasts, live chats, partner site visits, classroom visits, etc.
  • Collaborate with school leadership teams to assess professional development/training needs/opportunities, to include producing a comprehensive action plan/customized strategy for lasting engagement with devices in alignment with the district’s organizational strategy, as requested.
  • Train end users on particular device management tools, for example: GoGuardian, Google Classroom, Apple Classroom, JAMF Pro, and Apple School Manager (ASM).
  • Manage, maintain, support, and troubleshoot access to JAMF Pro and ASM.
  • Create, own, and/or assist in the development of knowledge content (i.e., training slide decks, device usage best practices, etc.) used by schools and the IT Service Desk to assist end users. Monitor and resolve applicable support requests or incidents via the internal ticketing system, recognizing priority tickets and taking action within the expected response time. Design, train, and support the use of GSuite and key Google applications across all device platforms.
  • Other duties as assigned.

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

Education:

  • Bachelor’s degree from an accredited college or university is required.
  • ITIL certification with an understanding of associated ITIL principles is preferred.
  • Microsoft Office Specialist certification or Microsoft Certified Professional Certification and/or Google Level 1 or Level 2 Certification is preferred.

Experience

  • Minimum of six (6) years of IT Enterprise experience, including a minimum of five (5) years experience with at least one device platform (Apple, Chrome, Windows) is required.
  • Previous experience with in-person and/or remote training and presenting to small and large groups is required.
  • Minimum of four (4) years Mobile Device Management (MDM) administration and support is preferred.
  • Previous experience with large deployments of over 500 users and sites including hands-on experience with enterprise mobility management technologies in an educational environment is preferred.
  • Practical instructional experience with one or more device platforms in the classroom - 1:1 classroom management and instruction is preferred.

Knowledge, Skills, and Abilities:

  • Proficiency with one or more device platforms (Apple, Chrome, Windows).
  • In-depth knowledge of troubleshooting a wide array of device usage issues.
  • Able to facilitate end user training on device technology with one or more platforms (Apple, Chrome, Windows).
  • Demonstrated analysis and investigation skills, with a structured approach to problem-solving.
  • Excellent customer service skills.
  • Strong interpersonal, verbal, and written communication, and organizational skills.
  • Experience using Google Suite apps
  • Proactive, decisive, action-oriented individual
  • Diligent in following team processes
  • Self-starter, with the ability to function independently and work in a team to contribute to the team’s success; willingness to share information

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.

Salary.com Estimation for Enterprise Technology Support Engagement Specialist in Chicago, IL
$71,915 to $89,307
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