AWS Windows Infrastructure Engineer

Phoenix Oversight Group LLC

2d • Remote

About The Position

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.

Requirements

• 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.

Nice To Haves

• 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.

Responsibilities

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level