Automates, hardens, deploys, and upgrades Windows Server infrastructure in AWS GovCloud. Builds hardened AMIs, provisions EC2 instances, automates patching and compliance, manages phased upgrades and rollback, integrates infrastructure automation with CI/CD, and documents configurations and runbooks. Requires strong PowerShell, Windows administration, AWS, infrastructure-as-code, and DevSecOps experience, plus eligibility for Public Trust clearance.
AWS Windows Infrastructure Engineer
Overview
The AWS Windows Infrastructure Automation Engineer automates the configuration, hardening, and deployment of a federal client's Windows Server infrastructure, hosted in a FedRAMP-authorized AWS GovCloud environment, in support of the upgrade from Windows Server 2016 to Windows Server 2019 or 2025. Working under the technical direction of the Windows Architect, the role turns upgrade designs and security baselines into automated, repeatable configurations so every server is built and maintained consistently across environment tiers.
Key Functions
- Automate Windows Server configuration, build, and deployment using configuration management tools (e.g., Ansible, PowerShell) and PowerShell scripting.
- Update existing Windows Server 2016 configuration baselines to Windows Server 2019/2025 standards and correct configuration drift.
- Build and maintain hardened Windows AMIs and automate EC2 provisioning for upgraded servers.
- Automate OS hardening and compliance checks (e.g., DISA STIGs, CIS Benchmarks, Group Policy) and remediate security findings.
- Execute upgrades in phased waves, including pre-upgrade backups/snapshots, post-upgrade validation, and automated rollback.
- Automate patching, inventory, and operational tasks using AWS Systems Manager.
- Automate certificate installation and renewal for upgraded servers and services.
- Integrate Windows automation into CI/CD pipelines (e.g., Jenkins, GitHub) with version-controlled, peer-reviewed code.
- Document automation, configurations, and runbooks in Confluence and track work in Jira.
Minimum Qualifications
- Bachelor’s degree and 5 years of relevant experience.
- An additional 2 years of experience (7 years total) with an Associate’s Degree in lieu of a Bachelor’s Degree.
- An additional 4 years of experience (9 years total) with a High School Diploma in lieu of a Bachelor’s Degree.
- Hands-on experience automating Windows Server configuration with Ansible, PowerShell DSC, or similar tools.
- Advanced PowerShell scripting skills.
- Experience supporting Windows Server 2016 to 2019 or 2025 upgrades or migrations in AWS.
- Experience automating Windows OS hardening, preferably in regulated federal or regulated industry.
- Working knowledge of AWS services for Windows workloads (EC2, AMIs, VPC, Systems Manager, EBS snapshots).
- Solid Windows Server administration skills (Active Directory, Group Policy, DNS, certificates, patching).
- Experience with infrastructure-as-code tools (e.g., Terraform, CloudFormation) or image-building tools (e.g., Packer, EC2 Image Builder).
- Experience with Git-based version control and CI/CD pipelines in an Agile, DevSecOps environment.
Preferred Qualifications or Skills
- Microsoft Windows Server certification (e.g., Microsoft Certified: Windows Server Administrator Associate) or AWS certification (e.g., AWS Certified SysOps Administrator – Associate).
- Experience integrating Windows servers with CyberArk for privileged access management.
- Experience in managing software deployments through group policy.
- Experience configuring Windows IIS servers and Power BI Gateway.
- Experience supporting federal government systems with audit and vulnerability management.
Position Details
- Employment type: Full-Time, W2
- Location: 100% Remote (US-based)
- Hours: 40 hours/week with availability during core business hours of 8am-5pm ET
- Eligibility: Must be eligible to obtain a Public Trust clearance
Similar Jobs
Artificial Intelligence • Fintech • Insurance • Marketing Tech • Software • Analytics
Under direct supervision, investigates and manages commercial property, casualty, disability, and automobile claims. Responsibilities include gathering facts, determining coverage and liability, evaluating losses, estimating costs, negotiating settlements, advising policyholders, maintaining claim files, and preparing reports. The role includes comprehensive training, mentoring, and on-the-job development, with hybrid attendance required twice monthly for candidates near select offices.
.png)
eCommerce • Fintech • Hardware • Payments • Software • Financial Services
The Strategic Account Manager is responsible for managing relationships with key Food & Beverage sellers, driving revenue growth through account management, providing technical solutions, and collaborating with cross-functional teams.
Top Skills:
Commerce TechnologyTechnical Solutions
Artificial Intelligence • Cloud • Information Technology • Sales • Security • Software • Cybersecurity
Set the technical direction for Rapid7’s LLM and agentic AI systems. Lead architecture, model strategy, fine-tuning, post-training, inference optimization, evaluation standards, and complex cross-team initiatives. Build critical model and inference code, mentor senior engineers, resolve technical trade-offs, and influence product and platform strategy across cybersecurity products.
Top Skills:
Agentic AiAWSClassical Machine LearningCudaDeepspeedDistributed TrainingDpoFsdpGrpoLlmsLoraPredictive AiPythonPyTorchQloraSglangTensorrt-LlmTransformer ArchitectureTritonVllm
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
