CPS-WINDOWS SERVER UPGRADE ENGINEER

Role Title: Windows Server Upgrade Engineer

Location: Chicago, IL

Duration: Long-term Contract

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

• Coordinate with application owners to schedule and perform comprehensive Windows Server OS upgrades, including in-place upgrades and new deployments (e.g., from 2012 to 2016/2019/2025) within a large-scale Hyper-V environment.
• Perform physical hardware upgrades on Dell R620 servers located at various school sites, leveraging Dell-specific tools including iDRAC, onboard flash memory, and Dell OpenManage Essentials (OME).
• Develop and utilize automation scripts using PowerShell, Ansible, or similar tools to streamline OS deployments, upgrades, and other repetitive tasks.
• Taking direction from managers or team leads, work independently to complete server provisioning and support tasks.
• Work with team members to provide cross-training on individual roles and responsibilities
• Manage day-to-day server operations, using standard tools
• Respond to and resolve alerts generated by Server Infrastructure monitoring tools
• Work with application teams to resolve issues as relates to software installation on to servers managed by Infrastructure Server Team.
• Consults with third party vendors to obtain support, make recommendations, and assist customers with their requests.
• Perform the initial input of Enterprise Server assets into the Server Asset database.
• Participate in Windows server On-Call rotation, which provides for an engineer to be available to deal with server emergencies on a 24x7 basis.

To be successful and achieve the above responsibilities, the Windows Server Engineer must possess the following qualifications:

Type of Education Preferred:

• Bachelor's Degree or equivalent

The following certifications are a plus but not required:

• MCSE

Type of Experience and Number of Years:

• 5 years or more experience managing Windows Server OS (2012, 2016, 2019, 2025) in an enterprise Hyper-V / System Center Virtual Machine Manager (SCVMM) environment.
• Expert-level Windows troubleshooting/triage experience.
• Demonstrated experience planning and executing OS upgrades, including in-place upgrades and new deployments.
• Hands-on experience with physical Dell server hardware (e.g., R620) and remote management tools, including iDRAC and Dell OpenManage Essentials (OME).
• Experience with Microsoft Failover Clustering, Host/OS Patching, Migrations, SCCM, and Azure administration.

Knowledge, Skills, and Abilities:

• Strong scripting and automation skills using PowerShell, Ansible, or similar technologies.
• Must possess strong planning, organizational, and prioritizing skills. Ability to manage multiple projects simultaneously.
• Experience with translating business requirements into IT specifications (strategy, platform selection, reference engineering designs)
• Must have good interpersonal, leadership, collaboration, facilitation and negotiation skills and be able to manage conflict.
• Must have excellent communication skills, and be able to explain complex technical issues in a way that non-technical people can understand as well as be able to explain customer needs and priorities in a way that technical people can understand.
• Must be dedicated to improving the lives of Students, Parents, Teachers and Principals through the judicious use of Information Technology.