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Remote Windows Deployment Jobs in Chicago, IL (NOW HIRING)

EXOS

Endpoint Management Engineer

Evanston, IL · Remote

Migrate and validate application packaging and deployment workflows * Support new application ... Ability to work independently in a remote environment * Strong communication and documentation ...

HirexHire

AI Cloud Engineer

Elk Grove Village, IL · Remote

$55 - $73.50/hr

Chicago, IL (Remote) Industry: E-Commerce Company Size: What They Do: Our client offers a powerful ... Develop and support CI/CD pipelines that improve deployment speed, reliability, and operational ...

HirexHire

AI Cloud Engineer

Elk Grove Village, IL · Remote

$55 - $73.50/hr

Chicago, IL (Remote) Industry: E-Commerce Company Size: What They Do: Our client offers a powerful ... Develop and support CI/CD pipelines that improve deployment speed, reliability, and operational ...

Inspira Financial

Cloud Engineer (Remote)

Oak Brook, IL · On-site +1

$56.25 - $75.25/hr

AZ-900, AZ-104 Skills & Abilities: • Minimum of 3 years of experience with: o Windows and/or Linux Operating systems that include building, security and deployment in both a physical and Cloud ...

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All JobsWindows Deployment JobsRemote Windows Deployment JobsRemote Windows Deployment Jobs in Chicago, IL

Remote Windows Deployment information

See Chicago, IL salary details

$23

$32

$46

How much do remote windows deployment jobs pay per hour?

As of Jul 31, 2026, the average hourly pay for remote windows deployment in Chicago, IL is $32.69, according to ZipRecruiter salary data. Most workers in this role earn between $25.00 and $43.32 per hour, depending on experience, location, and employer.

What is the difference between Remote Windows Deployment vs Remote Systems Administrator?

AspectRemote Windows DeploymentRemote Systems Administrator
Primary FocusDeploying and configuring Windows OS remotelyManaging and maintaining IT systems remotely
Required SkillsWindows OS, imaging tools, scriptingNetwork management, security, troubleshooting
CertificationsMicrosoft Certified: Windows Server, CompTIA A+Microsoft Certified: Azure Administrator, CompTIA Network+
Work EnvironmentIT support teams, deployment labsIT departments, enterprise networks

Remote Windows Deployment focuses on remotely installing and configuring Windows OS on devices, often during initial setup or updates. In contrast, Remote Systems Administrators oversee ongoing system health, security, and performance remotely. Both roles require technical certifications and work within IT environments, but their core responsibilities differ: deployment versus management.

What are the most commonly searched types of Windows Deployment jobs in Chicago, IL? The most popular types of Windows Deployment jobs in Chicago, IL are:
What are popular job titles related to Remote Windows Deployment jobs in Chicago, IL? For Remote Windows Deployment jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Windows Deployment jobs in Chicago, IL look for? The top searched job categories for Remote Windows Deployment jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Windows Deployment jobs? Cities near Chicago, IL with the most Remote Windows Deployment job openings:
Remote Windows Deployment jobs near you

Systems Engineer - Windows

Hudson River Trading

Chicago, IL • On-site, Remote

Other

Re-posted 7 days ago

Job description

Hudson River Trading (HRT) is seeking a Windows Systems Engineer to join our Enterprise Engineering team. In this role, you will help scale HRT's global hybrid Windows deployment and develop automation, configuration-as-code, and infrastructure-as-code solutions to seamlessly manage fleets of top-of-the-line user endpoints, mission critical servers, cloud infrastructure, and secure remote computing environments around the world. You will apply configuration-as-code practices to reduce operational overhead, build PowerShell-based systems that improve platform stability and resilience, and enhance the reliability of our Windows platform by designing and implementing automation that identifies and resolves technical inefficiencies across on-premises and Azure infrastructure.

The ideal candidate is a Microsoft-based technology engineer and eager problem solver who is comfortable working in a fast-paced environment. Terrific communication and collaboration skills, as well as a positive attitude towards team members and internal customers, are crucial to success within this role. 

Responsibilities

  • Leverage configuration-as-code paradigms to reduce the operational overhead of managing Windows infrastructure
  • Use infrastructure-as-code to consistently configure Microsoft Azure resources
  • Develop PowerShell-based systems to automate operational tasks and enhance the reliability of the Windows platform
  • Leverage automation to identify and remediate technical inefficiencies across Windows endpoints, Windows infrastructure, and Microsoft Azure resources
  • Participate in ongoing engineering, maintenance, and support efforts to improve the Windows environment

Qualifications

  • 10+ years of experience as a Microsoft-based technology engineer
  • Experience using Ansible (or similar configuration-as-code tool) to manage a fleet of Windows devices
  • Proven ability to provision Microsoft Azure resources with Terraform
  • Proficiency with Microsoft Graph API development
  • Experience developing scripts and tools using PowerShell
  • Familiarity with Microsoft Intune, Autopilot, Entra ID, and Active Directory
  • A general design approach that incorporates security best practices, business continuity, high availability, and scalability
  • A self-motivated and driven work ethic

The estimated base salary range for this position is 150,000 to 250,000 USD per year (or local equivalent). The base pay offered may vary depending on multiple individualized factors, including location, job-related knowledge, skills, and experience. This role will also be eligible for discretionary performance-based bonuses and a competitive benefits package.

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