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Chicago Public Schools (CPS) is one of the largest school districts in the United States, serving over 320,000 students in 600+ schools and employing approximately 40,000 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.  In order to fulfill this mission, we make three commitments to our students, their families, and all Chicagoans: academic progress, financial stability, and integrity.  Six core values are embedded within these commitments – student-centered, whole child, equity, academic excellence, community partnership, and continuous learning.

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 Device Management Manager, the Windows Management Engineer integrates and supports enterprise information systems management, including Windows systems (SME), server administration, virtualization, application packaging, networking, scripting automation, and classroom management applications. Working from a central location, this role is a Level III (resolver) resource in a tiered service desk hierarchy. The Windows Management Engineer ultimately supports teachers in educational institutions and implements end-user technology into the classroom, as well as supporting staff across the district to perform critical business functions. 

The Windows Management Engineer will be held accountable for the following responsibilities:

• Serves as the subject matter expert for the enterprise Windows Workstation OS Ecosystem
• Tests and deploys of new and updated software to Windows client systems
• Implements policy changes on clients via the most appropriate methods
• Develops and deploys Windows Image including building Windows OS Image for network-based deployment (PXE), USB image, and vendor factory imaging including crucial core applications
• Modifies source installation media for Windows Application Packaging to redeploy with customized configuration settings across the Windows fleet
• Supports the service desk, vendors, and Technical Coordinators as they support the schools and students.
• Creates and maintains documentation for Windows Management processes, procedures, and configurations 
• Defines and manages the device support lifecycle for Windows systems within the classroom and across the institution
• Manages and configures the Windows System, including, developing computer collections, managing advertisements, and deploying patches, updates, applications, and modifying configurations to ensure standardization as well as to improve the functionality of the enterprise fleet of devices using device management tools such as configuration manager, Intune, etc.
• Uses applications for device lockdown to prevent student tampering; monitoring/tracking tools to ensure student time-on-task; and efficient educator workflows.
• Assembles technical architecture documentation, as well as end-user training documentation, to disseminate to staff across the District
• Collaborates with support teams to help ensure standards are maintained, problems are addressed, field issues are understood and future states anticipated
• Updates all assigned tickets capturing troubleshooting activities and resolution, resolving escalations from the Service Desks
• Takes the lead for discovery and ownership of Windows desktop and related product issues
• Implements platform-agnostic and supportable solutions across Microsoft Windows, Apple macOS iOS, and ChromeOS
• Collaborates with teachers on Google Apps for Education on Windows devices
• Collaborates with the technology curriculum and educational assessment partners to ensure Windows devices are fully suitable for classroom usage and student assessments
• Other duties as assigned

In order to be successful and achieve the above responsibilities, the Windows Management Engineer must possess the following qualifications: 

Education and Experience Required: 

• High School Diploma or GED equivalent and a minimum of ten (10) years of professional experience in technology and a minimum of five (5) years of Windows system administration experience (Windows systems (SME), server administration, virtualization, application packaging, networking, and scripting automation is required); Associate degree preferred; or
• Bachelor’s degree from an accredited college or university and a minimum of five (5) years of professional experience in technology, including a minimum of five (5) years of Windows system administration experience (Windows systems (SME), server administration, virtualization, application packaging, networking, and scripting automation) is required; Computer Science, Engineering, or a related field, preferred 
• Experience with Classroom Management Technology, preferred
• Experience with Windows technology in the classroom, preferred
• Experience with OS image deployment leveraging MDT/WDS/PXE/Autopilot, preferred
• Mobile Device Management (MDM) administration experience, preferred
• Relevant industry certifications (e.g., CompTIA Certifications, CompTIA A+, Network+, Server+), preferred

Knowledge, Skills, and Abilities: 

• Ability to troubleshoot complex systems
• In-depth knowledge of client, network, and server-side troubleshooting methods
• Understanding of Windows configuration management via WMI, policy, registry, and scripting 
• Excellent verbal and written communication skills; capable of communicating and collaborating with a wide variety of internal and external stakeholders 
• Self-motivated with the ability to successfully prioritize tasks, as well as, function independently and collaboratively
• Familiarity with Hyper V virtual environment  
• Knowledge of TCP/IP and Wireless network (Wi-Fi) setup
• Analysis and investigation skills, with a structured approach to problem-solving
• Outstanding customer service skills.
• Knowledge of  Microsoft technologies (Active Directory, Configman, Intune, Azure AD)
• Knowledge of Chicago Public Schools’ network infrastructure
• Knowledge of wireless network (Wi-Fi) setup using enterprise-standard secure solutions
• In-depth knowledge of technical troubleshooting with Windows systems
• Ability to perform end-user training on Windows platforms
• Understanding of at least one enterprise-level configuration management tool such as Microsoft Configuration Manager, Windows InTune, etc.
• Familiarity with virtualization technologies and implementations in a distributed server and VDI ecosystem
• Strong interpersonal and organizational skills and demonstrated capability to abstract manual tasks into automated solutions

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.
• Be Fully Vaccinated Against COVID-19 -Unless approved for a medical or religious exemption, all employees are required to be up-to-date on COVID-19 vaccinations, including boosters, and to submit proof of vaccination to the district within 30 days of hire. “Up-to-date” on vaccination is defined as being at least two weeks past all primary vaccine doses and any applicable boosters.