Job Description
Are you a results-driven Windows Server Engineer ready to apply your expertise at true enterprise scale—where your work directly impacts the future of education?
Chicago Public Schools (CPS) is seeking a highly skilled and motivated Windows Server Engineer to join our Server Operations Team and play a vital role in powering the technology that supports a world-class learning experience for every student, in every school, and in every neighborhood. This role is central to the stability, security, and modernization of CPS’ vast infrastructure—spanning approximately 1,800 physical and virtual servers across Dell hardware platforms and a large-scale Hyper-V ecosystem.
This is a full-time, hybrid/on-site position with standard working hours of 9:00 AM to 5:00 PM CST, Monday through Friday. While the role offers flexibility through remote work, it also includes occasional on-site visits to CPS school locations, giving you the opportunity to work hands-on with mission-critical infrastructure where it matters most.
In this high-impact, hands-on role, you will lead the end-to-end lifecycle management of Windows Server environments, driving enterprise-wide OS upgrades and modern deployments across Windows Server 2012, 2016, 2019, and 2026. You will partner closely with application owners to align system requirements, define maintenance windows, and execute seamless deployments. Your expertise will also be applied on-site through hardware upgrades to Dell R620 servers, using tools such as iDRAC, onboard flash memory, and Dell OpenManage Essentials (OME). As a Tier III escalation point, you will respond to critical alerts, diagnose complex infrastructure issues, and ensure the ongoing performance, reliability, and security of CPS’ server environment.
Beyond operations, you will be a key driver of automation, efficiency, and innovation, developing and maintaining scripts using PowerShell, Ansible, and related technologies to streamline deployments, patching, migrations, and recurring workflows. You will work with a high level of autonomy while collaborating with technical leadership, support cross-training and knowledge sharing, partner with application teams on software installations and issue resolution, and engage with third-party vendors for advanced troubleshooting and solution evaluations. You will also ensure accurate enterprise server asset documentation and participate in a rotating 24x7 on-call schedule to protect CPS’ mission-critical systems at all times.
Required Experience & Technical Qualifications
5+ years of enterprise-level experience managing Windows Server OS (2012, 2016, 2019, 2026) within a Hyper-V / SCVMM environment
Expert-level Windows Server troubleshooting and triage experience in complex production environments
Proven success planning and executing OS upgrades, including in-place upgrades and full new server deployments
Hands-on experience with Dell physical server hardware (including Dell R620) and remote management tools such as iDRAC and Dell OpenManage Essentials (OME)
Experience with Microsoft Failover Clustering, Host/OS patching, system migrations, SCCM, and Azure administration
Required Skills
Strong scripting and automation skills using PowerShell, Ansible, or similar technologies
Excellent planning, organizational, and prioritization skills with the ability to manage multiple projects simultaneously
Proven ability to translate business requirements into IT specifications, including strategy development, platform selection, and reference engineering designs
Strong interpersonal, leadership, collaboration, facilitation, and negotiation skills, with the ability to manage conflict effectively
Outstanding verbal and written communication skills, including the ability to:
Explain complex technical issues in a clear, non-technical manner
Translate customer needs and business priorities into actionable technical requirements
Demonstrated commitment to using Information Technology to improve the lives of Students, Parents, Teachers, and Principals
If you are a highly driven engineer who thrives in complex environments and wants your technical expertise to serve a greater purpose, this is your opportunity. Apply now and help power the future of education at Chicago Public Schools.
Pay: $28.14 - $33.89 per hour
Expected hours: 40.0 per week
Education:
Bachelor's (Required)
Experience:
managing Windows Server OS (2012, 2016, 2019, 2026) : 5 years (Required)
License/Certification:
MCSE (Preferred)
Work Location: Hybrid remote in Chicago, IL 60602
Chicago Public Schools (CPS) is seeking a highly skilled and motivated Windows Server Engineer to join our Server Operations Team and play a vital role in powering the technology that supports a world-class learning experience for every student, in every school, and in every neighborhood. This role is central to the stability, security, and modernization of CPS’ vast infrastructure—spanning approximately 1,800 physical and virtual servers across Dell hardware platforms and a large-scale Hyper-V ecosystem.
This is a full-time, hybrid/on-site position with standard working hours of 9:00 AM to 5:00 PM CST, Monday through Friday. While the role offers flexibility through remote work, it also includes occasional on-site visits to CPS school locations, giving you the opportunity to work hands-on with mission-critical infrastructure where it matters most.
In this high-impact, hands-on role, you will lead the end-to-end lifecycle management of Windows Server environments, driving enterprise-wide OS upgrades and modern deployments across Windows Server 2012, 2016, 2019, and 2026. You will partner closely with application owners to align system requirements, define maintenance windows, and execute seamless deployments. Your expertise will also be applied on-site through hardware upgrades to Dell R620 servers, using tools such as iDRAC, onboard flash memory, and Dell OpenManage Essentials (OME). As a Tier III escalation point, you will respond to critical alerts, diagnose complex infrastructure issues, and ensure the ongoing performance, reliability, and security of CPS’ server environment.
Beyond operations, you will be a key driver of automation, efficiency, and innovation, developing and maintaining scripts using PowerShell, Ansible, and related technologies to streamline deployments, patching, migrations, and recurring workflows. You will work with a high level of autonomy while collaborating with technical leadership, support cross-training and knowledge sharing, partner with application teams on software installations and issue resolution, and engage with third-party vendors for advanced troubleshooting and solution evaluations. You will also ensure accurate enterprise server asset documentation and participate in a rotating 24x7 on-call schedule to protect CPS’ mission-critical systems at all times.
Required Experience & Technical Qualifications
5+ years of enterprise-level experience managing Windows Server OS (2012, 2016, 2019, 2026) within a Hyper-V / SCVMM environment
Expert-level Windows Server troubleshooting and triage experience in complex production environments
Proven success planning and executing OS upgrades, including in-place upgrades and full new server deployments
Hands-on experience with Dell physical server hardware (including Dell R620) and remote management tools such as iDRAC and Dell OpenManage Essentials (OME)
Experience with Microsoft Failover Clustering, Host/OS patching, system migrations, SCCM, and Azure administration
Required Skills
Strong scripting and automation skills using PowerShell, Ansible, or similar technologies
Excellent planning, organizational, and prioritization skills with the ability to manage multiple projects simultaneously
Proven ability to translate business requirements into IT specifications, including strategy development, platform selection, and reference engineering designs
Strong interpersonal, leadership, collaboration, facilitation, and negotiation skills, with the ability to manage conflict effectively
Outstanding verbal and written communication skills, including the ability to:
Explain complex technical issues in a clear, non-technical manner
Translate customer needs and business priorities into actionable technical requirements
Demonstrated commitment to using Information Technology to improve the lives of Students, Parents, Teachers, and Principals
If you are a highly driven engineer who thrives in complex environments and wants your technical expertise to serve a greater purpose, this is your opportunity. Apply now and help power the future of education at Chicago Public Schools.
Pay: $28.14 - $33.89 per hour
Expected hours: 40.0 per week
Education:
Bachelor's (Required)
Experience:
managing Windows Server OS (2012, 2016, 2019, 2026) : 5 years (Required)
License/Certification:
MCSE (Preferred)
Work Location: Hybrid remote in Chicago, IL 60602
💡 Quick Summary
Seeking a career-building opportunity? The Windows Server Upgrade Engineer- post position is now open for candidates interested in the IT Engineer & Developer Jobs sector. This role in Chicago offers a professional environment and growth potential.
Requirement Snapshot: Candidates should possess basic communication skills, a proactive attitude, and the ability to work in a team. Experience in IT Engineer & Developer Jobs is a plus.
