Windows Systems Engineer Expert

Cherokee Federal•Herndon, VA

About The Position

The Windows Systems Engineer - Expert will be responsible for managing and automating patch deployment and configuration management across multiple domains and enclaves. This role involves developing automation solutions using PowerShell, Python, APIs, or orchestration frameworks to streamline system updates and administrative tasks. The engineer will support hybrid and cloud patching capabilities using tools like Azure Update Management, AWS Systems Manager (SSM), and SCCM/ConfigMgr. Key responsibilities include engineering improvements to the enterprise patching infrastructure, designing a new automated update and hotfix distribution system, and performing automation-driven server configuration, baseline enforcement, compliance reporting, and STIG/vulnerability remediations. The position also requires providing Tier 3 troubleshooting and root-cause analysis for complex Windows systems, migrating and modernizing server workloads for cloud compatibility and virtualization, monitoring infrastructure performance with automated remediation, translating customer requirements into technical specifications, and preparing technical documentation. The role demands independent work in a fast-paced environment with strong communication and problem-solving skills, delivering excellent customer service and collaborating effectively with technical teams. Other job-related duties may be assigned.

Requirements

Active TS/SCI with Polygraph
Minimum of eleven (11) years of relevant experience
Bachelors' 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)
Must have Cloud certifications (Azure/AWS)
Strong, written and verbal communication skills
Strong documentation skills
Robust troubleshooting skills
Must pass pre-employment qualifications of Cherokee Federal
Must be a US Citizen AND possess an active TS/SCI with Polygraph clearance

Nice To Haves

Preferred to have Microsoft AZ900 and MS900 certifications
Experience in the following: Automation/orchestration tools such as AWS Lambda
Cloud-native monitoring tools (Azure Sentinel, CloudWatch) or Splunk automation
Creating enterprise-level documentation and architectural diagrams
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
Familiar with Azure
DevOps
Working knowledge of GIT Hub

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