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Windows Deployment Jobs in Illinois (NOW HIRING)

Gelber Group

Windows Administrator

Chicago, IL · On-site

$75K - $95K/yr

Build and maintain deployment images using Windows Deployment Services (WDS) and Microsoft Deployment Toolkit (MDT) * Apply basic networking knowledge including DHCP * Collaborate across ...

TEKsystems

Hardware Deployment Technician

Evanston, IL

$23/hr

Utilize deployment tools such as SCCM, Microsoft Intune, and Windows Autopilot to provision and manage endpoint devices. * Perform device migrations, workstation replacements, and hardware refresh ...

Posted today

TEKsystems

Hardware Deployment Technician

Evanston, IL

$23/hr

Utilize deployment tools such as SCCM, Microsoft Intune, and Windows Autopilot to provision and manage endpoint devices. * Perform device migrations, workstation replacements, and hardware refresh ...

New

Light Edge

Managed Services Technician

Chicago, IL · On-site

This position is for a full-time Administrator for deploying and configuring various Windows and Linux Operating Systems. This position will be responsible for the VM creation, OS deployment ...

US Bank

Senior Windows Endpoint Engineer

Chicago, IL · On-site

Support application packaging, deployment, and lifecycle management processes * Assist with Windows Autopilot and modern device management initiatives * Participate in platform upgrades, migrations ...

Lightedge

Managed Services Technician

Chicago, IL

This position is for a full-time Administrator for deploying and configuring various Windows and Linux Operating Systems. This position will be responsible for the VM creation, OS deployment ...

Lightedge

Managed Services Technician

Chicago, IL · On-site

This position is for a full-time Administrator for deploying and configuring various Windows and Linux Operating Systems. This position will be responsible for the VM creation, OS deployment ...

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Windows Deployment information

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How much do windows deployment jobs pay per hour?

As of Aug 23, 2026, the average hourly pay for windows deployment in Illinois is $30.75, according to ZipRecruiter salary data. Most workers in this role earn between $23.51 and $40.77 per hour, depending on experience, location, and employer.

What is a Windows Deployment?

A Windows Deployment job involves installing, configuring, and managing Windows operating systems across multiple devices in an organization. This includes using tools like Windows Deployment Services (WDS), Microsoft Deployment Toolkit (MDT), or System Center Configuration Manager (SCCM) to automate and streamline installations. Professionals in this role ensure systems are properly configured, secure, and optimized for performance. They may also handle troubleshooting, updates, and migration to newer Windows versions.

What are the key skills and qualifications needed to thrive in Windows Deployment?

To thrive in a Windows Deployment role, you need a solid understanding of Microsoft Windows operating systems, imaging and deployment methodologies, and networking fundamentals—often backed by relevant IT certifications such as CompTIA A+, Microsoft Certified: Modern Desktop Administrator Associate, or similar. Hands-on experience with deployment tools like Microsoft Deployment Toolkit (MDT), Windows Deployment Services (WDS), and System Center Configuration Manager (SCCM) is highly valuable. Strong problem-solving skills, attention to detail, effective communication, and the ability to work both independently and in teams set top candidates apart. These capabilities are vital to ensure seamless rollouts, rapid troubleshooting, and successful user adoption in diverse business environments.

What are some of the most common challenges faced by professionals working in Windows Deployment?

Windows Deployment professionals often encounter challenges such as managing hardware and software compatibility across different devices, troubleshooting deployment failures, and ensuring minimal downtime for end users. Staying current with evolving deployment technologies and best practices is also essential, as is handling large-scale rollouts efficiently. On a day-to-day basis, you may work closely with IT support, network engineers, and end users to coordinate upgrades, resolve issues, and refine deployment processes. Overcoming these challenges requires both technical expertise and strong communication skills, making the role both dynamic and rewarding.

What are the most commonly searched types of Windows Deployment jobs in Illinois?

The most popular types of Windows Deployment jobs in Illinois are:

What are popular job titles related to Windows Deployment jobs in Illinois?

For Windows Deployment jobs in Illinois, the most frequently searched job titles are:

What job categories do people searching Windows Deployment jobs in Illinois look for?

The top searched job categories for Windows Deployment jobs in Illinois are:

Windows Deployment jobs near you
Infographic showing various Windows Deployment job openings in Illinois as of August 2026, with employment types broken down into 94% Full Time, 2% Part Time, and 4% Contract. Highlights an 84% Physical, 5% Hybrid, and 11% Remote job distribution, with an average salary of $63,955 per year, or $30.7 per hour.

Systems Engineer - Windows

Hudson River Trading

Chicago, IL • On-site, Remote

Full-time

Re-posted 7 hours 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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