Haystack
← Back to Jobs
Technology

Windows Server Engineer

GDHSpringdale, AR🇺🇸United StatesPosted 10 Jul 2026

Why This Role Stands Out

This on-site Windows Server Engineer role offers a fantastic opportunity to lead critical modernization efforts, upgrading legacy systems to the latest Windows Server versions and contributing to cloud readiness. You'll thrive here if you have a strong background in Windows Server administration and a passion for infrastructure automation and security, with a competitive hourly rate of $50-$60. Don't miss out on this chance to significantly impact enterprise infrastructure and grow your skills!

Quick Overview

Salary
$50 - $60/hr
Work Type
On Site
Level
Mid Senior

Job Description

Role Summary
A Windows Server Engineer is responsible for leading enterprise-wide end-of-support (EOS) remediation and modernizing Windows Server environments within a hybrid infrastructure. This role involves planning and executing upgrades from legacy systems (2008/2012) to the latest Windows Server versions, including Windows Server 2025, while ensuring system stability, security, and readiness for cloud deployment. The position requires collaboration with cross-functional teams to support application migrations, automation, and infrastructure improvements at a senior level.

Responsibilities

  • Lead EOS remediation efforts for Windows Server 2008 and 2012 environments.
  • Plan, coordinate, and execute server upgrade and rehosting strategies to Windows Server 2025.
  • Assess system vulnerabilities, implement remediation, and ensure security compliance.
  • Support application migrations across VMware ESXi and AWS EC2 platforms.
  • Automate server provisioning and configuration using infrastructure-as-code tools such as PowerShell, Terraform, or Ansible.
  • Collaborate with application and development teams to ensure compatibility during modernization initiatives.
  • Standardize build, patching, and configuration processes across server environments.
  • Implement and maintain CI/CD pipelines supporting infrastructure deployment and management.
  • Improve system performance, operational stability, and resilience through ongoing optimization.
  • Monitor and manage infrastructure risks, ensuring continuous security and operational compliance.

Qualifications

  • Extensive experience with Windows Server administration (2008–2022+), including upgrades and lifecycle management.
  • Proven track record with OS migrations and infrastructure modernization.
  • Hands-on experience with VMware ESXi and AWS EC2 cloud platforms.
  • Strong knowledge of Active Directory, Group Policy, DNS, and patch management procedures.
  • Proficiency with automation and scripting tools such as PowerShell, Terraform, and Ansible.
  • Understanding of security hardening, vulnerability assessment, and remediation practices.
  • Ability to work effectively in a collaborative team environment.
  • Excellent problem-solving skills and attention to detail.
  • Availability for on-site work with flexibility to manage project timelines.
  • Must be legally authorized to work in the United States.

Publishing Pay Range: $50.00 - $60.00 hour

This position is based in office and requires employee to work on-site.

Skills

AWS
Active Directory
Ansible
DNS
PowerShell
Terraform
VMware

Similar jobs