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
Handles inbound calls and warm leads to understand customers’ insurance needs, recommend appropriate property and casualty coverages, and convert prospects into policyholders. The role includes paid training and licensing support, customer relationship building, persuasive sales, and adherence to remote-work requirements. Representatives must work a variable weekday and weekend schedule, maintain a dedicated workspace, and use a wired high-speed internet connection.
Top Skills:
Cable/Fiber/Dsl High-Speed InternetPc
Artificial Intelligence • Fintech • Insurance • Marketing Tech • Software • Analytics
Leads enterprise operational risk management by advising business leaders, identifying and monitoring risks, evaluating internal controls, managing operational events and remediation, conducting root cause analysis, and preparing risk reporting for senior management. Maintains risk policies and governance practices, collaborates with compliance and audit teams, and assesses risks associated with AI tools and business use cases.
Top Skills:
Ai ToolsEnterprise Risk Management FrameworksInternal Control FrameworksRisk Dashboards
Artificial Intelligence • Fintech • Insurance • Marketing Tech • Software • Analytics
Investigates, evaluates, and resolves complex environmental, auto, and general liability claims. Responsibilities include analyzing coverage and policy provisions, determining liability and damages, managing litigation, coordinating with counsel and consultants, maintaining reserves, negotiating settlements, identifying fraud and subrogation opportunities, and recommending case strategies. The role also communicates with policyholders, monitors trials, maintains action plans, and trains less experienced staff.
What you need to know about the Boston Tech Scene
Boston is a powerhouse for technology innovation thanks to world-class research universities like MIT and Harvard and a robust pipeline of venture capital investment. Host to the first telephone call and one of the first general-purpose computers ever put into use, Boston is now a hub for biotechnology, robotics and artificial intelligence — though it’s also home to several B2B software giants. So it’s no surprise that the city consistently ranks among the greatest startup ecosystems in the world.
Key Facts About Boston Tech
- Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
- Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
- Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
- Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories
