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We are seeking an experienced L2 Windows Systems Engineer to join our Infrastructure team. In this role, you will be dedicated to supporting a leading workers’ compensation and catastrophic care management client, focusing on proactive monitoring, patching, maintenance, and documentation of their Windows-based infrastructure in a hybrid environment (on-premises + Azure). You will ensure system stability, security, and compliance through independent ownership of operational tasks, building runbooks/SOPs, and maintaining clear escalation paths.
Job Responsibility:
Monitor critical Windows servers, VMs, and infrastructure using PRTG Network Monitor, Azure Monitor, and related tools
proactively respond to alerts and investigate performance trends for the client environment
Execute and manage Windows OS patching (monthly security updates, cumulative updates, emergency patches), software stack updates, and OS-layer patching in virtualized environments (e.g., Citrix App Layering or similar)
Perform controlled testing and deployment of patches/updates with minimal disruption, including rollback planning
Build, maintain, and continuously improve runbooks, Standard Operating Procedures (SOPs), and knowledge articles for patching, maintenance, recovery, and common operational tasks
Develop and own monitoring dashboards and alert configurations in PRTG/Azure for infrastructure health
Analyze system trends, patch compliance rates, and alert patterns
recommend proactive improvements to enhance reliability
Maintain detailed documentation of escalation paths, RACI matrices, and handoff procedures for complex issues
Collaborate with cross-functional teams to support infrastructure stability in a regulated healthcare environment
Requirements:
Bachelor's degree in Computer Science, Information Technology, Engineering, or equivalent (or relevant experience/certifications in lieu)
7+ years of hands-on experience in Windows Server administration and support (Windows Server 2016/2019/2022 preferred)
Strong expertise in large-scale patching and update management (WSUS, SCCM/MECM, PowerShell scripting, or manual methods)
Experience with PRTG Network Monitor for infrastructure and server monitoring (sensor configuration, dashboards, alerts)
Proficiency in PowerShell scripting for automation and task management
Familiarity with virtualization/layering technologies (Citrix, VMware, or equivalent) is highly desirable
Exposure to Azure infrastructure (VMs, monitoring) and hybrid environments
Understanding of change management and compliance processes (healthcare exposure is a plus)
Proven ability to work independently, document thoroughly, and escalate judiciously
Nice to have:
Relevant certifications (e.g., Microsoft Certified: Windows Server, Azure Administrator)
Experience supporting regulated healthcare or workers' compensation environments