Windows Server 2016 Upgrade and Build Engineer

Job Description: Role OverviewThis role supports the Windows Server 2016 Retirement Program, ensuring all servers are upgraded or rebuilt to meet compliance and security standards before the January 2027 end-of-life deadline. The resource will work closely with Platform Engineering, Platform Operations, and application owners to execute upgrade workflows across VMware, Nutanix, Azure, and AWS environments, while adhering to corporate standards for automation, monitoring, and security.Key ResponsibilitiesUpgrade ExecutionPerform in-place upgrades and new builds for Windows Server 2016 to supported OS versions.Validate upgrade paths and ensure minimal downtime during migrations.Automation and ScriptingRead and understand PowerShell scripts for upgrade automation.Execute automation workflows into Azure DevOps pipelines.Infrastructure IntegrationConfigure servers for compliance with enterprise standards (GPOs, baseline hardening).Ensure integration with management tools: BigFix, Splunk, SCOM, CyberArk.Security EnablementDeploy and validate security agents (CrowdStrike, Morphisec).Confirm adherence to CIS benchmarks and internal security posture requirements.Documentation and ReportingMaintain accurate upgrade logs and configuration documentation.Provide status updates and participate in weekly planning/progress meetings.Required Skills and ExperienceTechnical ExpertiseStrong experience with Windows Server administration (2016/2019/2022).Familiarity with VMware, Nutanix, and AWS ..... full job details .....