Windows Systems Engineer Expert

• 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

• Active TS/SCI with Polygraph
• Must have a minimum of eleven (11 ) years of relevant experience
• Have a Bachelors’ Degree, in a related field of study.
• Significant engineering experience supporting Windows platform environments
• Experience in Advanced PowerShell scripting
• Must have experience with WSUS across multiple enclaves and in offline/air-gapped systems.
• Familiarity with cloud patching tools (Azure Update Management, AWS SSM)
• Have f amiliarity with SCCM/ConfigMgr or similar enterprise patching tools
• Experience with vulnerability remediation automation and STIG compliance workflows virtualization & Infrastructure
• 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)
• Preferred to have Microsoft AZ900 and MS900 certifications.
• Must have 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
• Strong, written and verbal communication skills
• Strong documentation skills
• Robust troubleshooting skills
• Must pass pre-employment qualifications of Cherokee Federal, * Microsoft Azure
• Virtual Desktop Infrastructure
• Windows Server
• Troubleshooting skills
• Microsoft Defender

Pay commensurate with experience, Full time benefits include Medical, Dental, Vision, 401K, and other possible benefits as provided. Benefits are subject to change with or without notice.

Cherokee Preting (Preting) is a part of Cherokee Federal - the division of tribally owned federal contracting companies owned by Cherokee Nation Businesses. As a trusted partner for more than 60 federal clients, Cherokee Federal LLCs are focused on building a brighter future, solving complex challenges, and serving the government’s mission with compassion and heart. To learn more about Preting, visit cherokee-federal.com.