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 enterp…
Skills: Windows Systems Engineering, PowerShell, Python, Automation, Patch Management
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Full-time
bachelor degree
Medical, Dental, Vision, 401k
Posted 17d ago
~40 hrs/week
Responsibilities
The Windows Systems Engineer will manage and automate patch deployment and configuration management across complex, heterogeneous IT environments. They will also perform root-cause analysis, modernize server workloads, and ensure compliance with security standards.
Requirements
Candidates must possess an active TS/SCI with Polygraph clearance and at least eleven years of relevant experience. A bachelor's degree in a related field is required, along with strong expertise in Windows platform engineering and automation tools.
Full job description
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
AWS services includingVPC, 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.
Cherokee Federal is a top 100 federal contractor advancing America’s interests worldwide through innovative solutions in defense, technology, health and intelligence.
With proven expertise that delivers and transformative impact that endures, Cherokee Federal empowers mission success for more than 60 U.S. federal agencies. We provide the people, systems, infrastructure and operations that keep critical missions performing in the real world.
As the federal contracting division of Cherokee Nation Businesses, Cherokee Federal combines deep technical expertise with a purpose-driven approach to solving today’s most complex challenges while preparing for tomorrow’s mission. Our success supports Cherokee Nation, the largest Native American tribe in the United States, by helping fund programs and services that strengthen Cherokee communities for generations to come.
Offices: 2 W 2nd St, 1500, Tulsa, Oklahoma 74103, US
Federal ContractingNon ProfitProfessional ServicesGovernmentPublic Relations
How much do Security & Safety jobs in Herndon, VA pay?
Based on 569 listings with disclosed salaries, most security & safety jobs in Herndon, VA pay between $92k–$216k per year. Individual offers vary with seniority, company size, and specialization.
How many Security & Safety jobs are open in Herndon, VA right now?
There are currently 688 open security & safety positions in Herndon, VA listed on Clera. New openings are added daily as companies post roles.
Which companies are hiring for Security & Safety roles in Herndon, VA?
Companies currently hiring include Amazon, Peraton, General Dynamics Information Technology, Dark Wolf, VT Group (VTG), among others. Browse the listings above to see every active employer.
Are there remote or hybrid Security & Safety jobs in Herndon, VA?
Yes — 118 of the 688 open security & safety positions offer remote or hybrid work (25 remote, 93 hybrid).
How do I apply for Security & Safety jobs in Herndon, VA?
Each listing links directly to the employer's application page. Apply early — fresh listings get the most recruiter attention in the first two weeks.