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Windows Server Engineer (Terraform, CICD, Kubernetes)

Request Technology, LLC
Chicago, IL Full Time
POSTED ON 11/26/2025
AVAILABLE BEFORE 12/25/2025

***Hybrid, 3 days onsite, 2 days remote***

***We are unable to sponsor as this is a permanent full-time role***

A prestigious company is looking for a Windows Administrator (AWS, VMware, CICD, Automation). This role is focused on AWS/On-prem Windows server 2016, 2019, 2022 administration, CICD pipeline automation, Terraform, Ansible, Jenkins, VMware, etc.

Responsibilities:

  • Administer, support, and optimize Windows Server environments (2016, 2019, 2022) across on-prem and AWS.
  • Design and maintain automated CI/CD pipelines for server builds and AMIs using Jenkins, Terraform, Ansible, and Packer.
  • Manage hybrid infrastructure including VMware-based virtualization (vSphere, ESXi, vCenter) and AWS cloud workloads.
  • Troubleshoot complex system, OS, and application issues; collaborate with vendors and cross-functional teams for resolution.
  • Automate infrastructure provisioning, patching, and operational tasks to reduce manual effort and increase reliability.
  • Participate in security patching, hardening, and vulnerability remediation.
  • Provide input on infrastructure modernization initiatives, including container platforms (Kubernetes as a plus).

Qualifications

  • Bachelor s degree in computer science, Information Technology, or related field preferred.
  • Professional Experience: 7 years of Windows Server engineering and infrastructure support in enterprise environments, with at least 2 3 years in hybrid (on-prem AWS) environments.
  • Platform Skills: Strong Windows Server expertise; experience with VMware, AWS, and hybrid infrastructure. Exposure to Kubernetes/container platforms is a plus.
  • Solution Design: Proven ability to build automated, reliable, and secure infrastructure solutions leveraging IaC and CI/CD pipelines.
  • Advanced administration of Windows Server 2016, 2019, 2022.
  • Hands-on experience with CI/CD pipelines and automation (Terraform, Ansible, Jenkins, Packer).
  • Experience building and maintaining custom AMIs and golden images.
  • VMware administration (vSphere, ESXi, vCenter) and virtualization concepts.
  • AWS experience with EC2, networking, and hybrid integrations.
  • PowerShell scripting; experience with Python or Bash scripting is a plus.
  • Active Directory and Group Policy administration.
  • Networking fundamentals (TCP/IP, DNS, DHCP, VLANs, firewalls, load balancers).
  • Vulnerability remediation and patch management experience.

Salary : $150,000 - $170,000

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