Windows Systems Engineer Expert

Compensation & Benefits

Estimated Starting Salary Range: $190,939. Full time benefits include Medical, Dental, Vision, 401K, and other possible benefits as provided.

Responsibilities

• Manage and automate patch deployment and configuration management across multiple domains and enclaves.
• Develop automation solutions using PowerShell, Python, APIs, or orchestration frameworks to streamline system updates and administrative tasks.
• Support hybrid and cloud patching capabilities using tools such as Azure Update Management, AWS Systems Manager (SSM), and SCCM/ConfigMgr.
• Engineer improvements to the enterprise patching infrastructure and contribute to the design of a new automated update and hotfix distribution system.
• Perform automation-driven server configuration, baseline enforcement, compliance reporting, and STIG/vulnerability remediations.
• Provide Tier 3 troubleshooting and root-cause analysis for complex Windows systems.
• Migrate, refactor, and modernize traditional server workloads to support cloud compatibility and virtualization strategies.
• Monitor infrastructure performance, proactively identify issues, and implement automated remediation with minimal user impact.
• Translate customer requirements into hardware/software specifications and perform system integration, verification, and validation.
• Prepare technical documentation, diagrams, and patching process workflows for customer and team use.
• Work independently in a fast-paced environment while maintaining strong communication and problem-solving skills.
• Deliver strong customer service and collaborate effectively with technical teams.
• Performs other job-related duties as assigned.

Qualifications

• Active TS/SCI with Polygraph.
• Minimum of eleven (11) years of relevant experience.
• Bachelor's Degree in a related field of study.
• Significant engineering experience supporting Windows platform environments.
• Experience in Advanced PowerShell scripting.
• Experience with WSUS across multiple enclaves and in offline/air-gapped systems.
• Familiarity with cloud patching tools (Azure Update Management, AWS SSM).
• Familiarity with SCCM/ConfigMgr or similar enterprise patching tools.
• Experience with vulnerability remediation automation and STIG compliance workflows.
• Experience with VMware (vSphere 4.x–6.x) and Microsoft Hyper-V (2016–2022).
• Knowledge of commercial cloud providers including Azure, Google Cloud (GCP), and Oracle Cloud (OCI).
• Cloud certifications (Azure/AWS).
• Preferred: Microsoft AZ900 and MS900 certifications.
• Experience with automation/orchestration tools such as AWS Lambda.
• Experience with cloud-native monitoring tools (Azure Sentinel, CloudWatch) or Splunk automation.
• Experience creating enterprise-level documentation and architectural diagrams.
• Experience with DSC, CI/CD pipelines, GitHub/GitLab, Jenkins Pipeline.
• AWS services including VPC, EC2, ELB, S3, IAM, Security Groups, Fleet Manager, and EventBridge to perform a variety of engineering analyses, software, hardware, development, integration, testing, maintenance tasks, and support duties.
• Working knowledge of Virtual Desktop Infrastructure.
• Familiarity with Azure DevOps.
• Working knowledge of GIT Hub.
• Strong written and verbal communication skills.
• Strong documentation skills.
• Robust troubleshooting skills.
• Must pass pre-employment qualifications of Cherokee Federal.