Lead Windows Infrastructure Engineer

WiseHire are looking for a seasoned Windows Infrastructure Engineer to join a growing technology team. This role focuses on maintaining and evolving a robust Windows server environment, both on-prem and in the cloud. You’ll be working in a fast-paced, collaborative setting that values automation, cloud-native solutions, and continuous improvement.

If you're someone who thrives in both structured enterprise environments and flexible DevOps ecosystems, this opportunity could be a great fit.

Key Responsibilities:

• Lead support and administration efforts for Windows Server ecosystems (2016–2022) across virtual and physical infrastructures
• Manage cloud-hosted systems—particularly AWS—and assist in their evolution through Infrastructure-as-Code (IaC) practices
• Build and maintain automation pipelines using tools such as Jenkins, Ansible, Terraform, and Packer
• Provide timely support for system outages, OS-level bugs, and third-party software issues
• Actively participate in patching cycles, compliance initiatives, and vulnerability mitigation
• Work cross-functionally with various technical teams and vendors to diagnose complex system issues
• Champion process automation to streamline administrative workflows

What You Bring:

• Deep understanding of Windows Server environments (2016, 2019, 2022)
• Practical experience in cloud infrastructure—AWS strongly preferred
• Proficient in PowerShell scripting and system-level automation
• Strong grasp of IaC tools (Terraform, Ansible), and CI/CD workflows
• Familiarity with virtualization technologies like VMware
• Comfortable managing Active Directory and supporting virtualized Windows environments
• Working knowledge of storage technologies such as NAS/SAN and basic networking concepts
• Previous experience with automated builds, server hardening, and vulnerability remediation is a bonus

Ideal Profile:

• 7 years in enterprise-level Windows systems administration
• Adept at troubleshooting, team collaboration, and working under pressure
• Strong interpersonal communication and documentation skills
• Experience supporting large distributed teams or organizations
• Self-motivated with a keen attention to detail and a passion for automation

Why Join Us?

• $140-160k base compensation
• 15% annual bonus
• Flexible hybrid working model—up to two days remote weekly
• Health benefits including medical, dental, and vision coverage
• Generous parental leave, vacation time, and wellness support
• 401(k) with employer contribution (6%)

This is a hybrid role based in Chicago and is not open to visa sponsorship.