Krasan Consulting Services
Windows Server Upgrade Engineer (Chicago)
Krasan Consulting Services, Chicago, Illinois, United States, 60290
Job Summary:
The Windows Server Upgrade Engineer will be part of a Server Operations team and will support the day-to-day technical operations of a large-scale infrastructure environment consisting of approximately 1,800 physical and virtual servers running on Dell hardware and Hyper-V. This role involves assessing complex technical issues, recommending and implementing solutions, and providing administration and oversight for server hardware and software infrastructure. The ideal candidate is a self-starter who can independently drive tasks to completion and quickly adapt to changing technical demands.
Key Responsibilities: Coordinate with application owners to schedule and perform comprehensive Windows Server OS upgrades, including in-place upgrades and new deployments (e.g., 2012 to 2016/2019/2025) within a large-scale Hyper-V environment. Perform physical hardware upgrades on Dell R620 servers across multiple sites, using Dell tools such as 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 repetitive operational tasks. Work independently, taking direction from managers or team leads to complete server provisioning and support activities. Collaborate with team members to provide cross-training on roles and responsibilities. Manage day-to-day server operations using standard enterprise tools. Respond to and resolve alerts generated by server infrastructure monitoring systems. Work closely with application teams to resolve software installation and compatibility issues on managed servers. Coordinate with third-party vendors for support, recommendations, and issue resolution. Perform initial entry of enterprise server assets into the server asset management database. Participate in a 24x7 Windows Server on-call rotation to support critical server emergencies.
Education & Certifications: Bachelors degree or equivalent experience preferred. Microsoft certifications (e.g., MCSE) are a plus but not required.
Experience Requirements: 5+ years of experience managing Windows Server OS (2012, 2016, 2019, 2025) in an enterprise Hyper-V / SCVMM environment. Expert-level Windows troubleshooting and triage experience. Proven experience planning and executing OS upgrades, including in-place upgrades and new deployments. Hands-on experience with Dell server hardware (e.g., R620) and remote management tools such as 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. Excellent planning, organizational, and prioritization skills, with the ability to manage multiple projects simultaneously. Experience translating business requirements into IT specifications, including strategy, platform selection, and reference architecture designs. Strong interpersonal, collaboration, leadership, facilitation, and conflict-management skills. Excellent communication skills, with the ability to clearly explain complex technical concepts to both technical and non-technical audiences. Strong commitment to leveraging information technology to positively support organizational and community outcomes.
2009
Key Responsibilities: Coordinate with application owners to schedule and perform comprehensive Windows Server OS upgrades, including in-place upgrades and new deployments (e.g., 2012 to 2016/2019/2025) within a large-scale Hyper-V environment. Perform physical hardware upgrades on Dell R620 servers across multiple sites, using Dell tools such as 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 repetitive operational tasks. Work independently, taking direction from managers or team leads to complete server provisioning and support activities. Collaborate with team members to provide cross-training on roles and responsibilities. Manage day-to-day server operations using standard enterprise tools. Respond to and resolve alerts generated by server infrastructure monitoring systems. Work closely with application teams to resolve software installation and compatibility issues on managed servers. Coordinate with third-party vendors for support, recommendations, and issue resolution. Perform initial entry of enterprise server assets into the server asset management database. Participate in a 24x7 Windows Server on-call rotation to support critical server emergencies.
Education & Certifications: Bachelors degree or equivalent experience preferred. Microsoft certifications (e.g., MCSE) are a plus but not required.
Experience Requirements: 5+ years of experience managing Windows Server OS (2012, 2016, 2019, 2025) in an enterprise Hyper-V / SCVMM environment. Expert-level Windows troubleshooting and triage experience. Proven experience planning and executing OS upgrades, including in-place upgrades and new deployments. Hands-on experience with Dell server hardware (e.g., R620) and remote management tools such as 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. Excellent planning, organizational, and prioritization skills, with the ability to manage multiple projects simultaneously. Experience translating business requirements into IT specifications, including strategy, platform selection, and reference architecture designs. Strong interpersonal, collaboration, leadership, facilitation, and conflict-management skills. Excellent communication skills, with the ability to clearly explain complex technical concepts to both technical and non-technical audiences. Strong commitment to leveraging information technology to positively support organizational and community outcomes.
2009