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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Enterprise Technology Support Engagement Specialist - **Company:** Chicago Public Schools - **Location:** Bridgeport, CT, United States - **Experience:** Experienced - **Contract:** Permanent contract - **Skills:** Microsoft Windows, Issue Tracking Systems, Microsoft Office, Software Tools, Enterprise Software Applications, Google Classroom, Casper Suite, Gsuite, Communication Devices - **Published:** August 24, 2026 - **Apply:** https://cpsk12il.taleo.net/careersection/3/jobdetail.ftl?job=250002F1 ## About the Role * 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., * 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 ## Description 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 CPS^TM 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. 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