Windows Systems Engineer Expert

Windows Systems Engineer - Expert

This position requires an active TS/SCI with Polygraph clearance to be considered.

Cherokee Preting is seeking an experienced Windows Systems Engineer – Expert to support multiple enterprise domains. This role is responsible for engineering, automating, and maintaining patching and configuration management solutions across a complex, heterogeneous IT environment spanning physical, virtual, and cloud-based systems.

Compensation & Benefits:

Estimated Starting Salary Range for Windows Systems Engineer - Expert: $190,939

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.

Windows Systems Engineer - Expert Responsibilities Include:

• 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

Windows Systems Engineer - Expert Experience, Education, Skills, Abilities requested:

• 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 familiarity 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

Company Information: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.

#CherokeeFederal #LI-CK2 #IntelCareers

Cherokee Federal is a military friendly employer. Veterans and active military transitioning to civilian status are encouraged to apply.

Legal Disclaimer: Cherokee Federal is an equal opportunity employer. Please visit cherokee-federal.com/careers for information regarding our Affirmative Action and Equal Opportunity Employer Statement, and Accommodation request.

Many of our job openings require access to government buildings or military installations. Candidates must pass pre-employment qualifications of Cherokee Federal.

As required by our governmental client, this position requires being a US Citizen AND an active TS/SCI with Polygraph clearance.

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