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Windows Deployment Jobs in Wisconsin (NOW HIRING)

CLEAResult

WI · On-site

$120 - $130/hr

... windows, and go/no-go criteria. * Design, maintain, and optimize CI/CD pipelines in Azure DevOps Pipelines and GitHub Actions, including build, test, artifact, and deployment stages. * Manage ...

Progress

DevOps Engineer II

Madison, WI · On-site +1

$83K - $97K/yr

We are seeking a DevOps Engineer to lead automation of deployment and upgrade processes for our Windows-based software products in Azure, while also contributing directly to the maintenance and ...

Progress

DevOps Engineer II

Madison, WI · On-site +1

$83K - $97K/yr

We are seeking a DevOps Engineer to lead automation of deployment and upgrade processes for our Windows-based software products in Azure, while also contributing directly to the maintenance and ...

Progress

DevOps Engineer II

Madison, WI · On-site +1

$83K - $97K/yr

We are seeking a DevOps Engineer to lead automation of deployment and upgrade processes for our Windows-based software products in Azure, while also contributing directly to the maintenance and ...

Progress

DevOps Engineer II

Madison, WI · On-site +1

We are seeking a DevOps Engineer to lead automation of deployment and upgrade processes for our Windows-based software products in Azure, while also contributing directly to the maintenance and ...

Andersen Windows, Inc.

Manager I Engineering

Menomonie, WI · On-site

$111.14 - $172.26/hr

Our portfolio of brands -- Andersen Windows & Doors, Renewal by Andersen and Fenetres MQ -- is ... Define and communicate performance targets established through strategy deployment for safety ...

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$22

$32

$45

How much do windows deployment jobs pay per hour?

As of Aug 14, 2026, the average hourly pay for windows deployment in Wisconsin is $32.03, according to ZipRecruiter salary data. Most workers in this role earn between $24.52 and $42.45 per hour, depending on experience, location, and employer.

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 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 popular job titles related to Windows Deployment jobs in Wisconsin?

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

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

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

Windows Deployment jobs near you
Infographic showing various Windows Deployment job openings in Wisconsin as of August 2026, with employment types broken down into 87% Full Time, 7% Part Time, and 6% Contract. Highlights an 84% Physical, 5% Hybrid, and 11% Remote job distribution, with an average salary of $66,617 per year, or $32 per hour.

Senior Microsoft Windows Field Deployment Technician

MKS2 Technologies

Milwaukee, WI

$60K - $70K/yr

Full-time

Posted 7 days ago

Job description

Sr. Microsoft Windows Field Deployment Technician 

Location: Milwaukee, WI

Pay rate: $60,000 - $70,000 annually with full benefits
As a Senior Microsoft Windows Field Deployment Technician on our project, you'll work with a team of onsite technicians supporting the VA's EHR deployment and training project and assist with oversight of workload.  In this role you will be deploying, imaging, and setting up equipment (PCs, Laptops, Docking Stations, Monitors, Printers, Scanners, and Network Connections) around the VA medical center campus as well as offsite training centers.  This role combines strong technical skills with an emphasis on delivering a high level of customer service.  You will be responsible for unboxing, setting up, installing, configuring, removing equipment, re-packaging hardware for shipment, and with limited supervision.  This role will also require setup of equipment at various training sites, verifying each computer has the most current VA computer image, computer is available for scheduled security scans and update, Active Directory assignment for training use, configure network connectivity in the training room, and computer peripherals are installed at each training seat. You will be managing inventory and network connectivity at each training site and ensuring connectivity during all training sessions.  This position is located onsite at Veterans' Administration Medical Centers and offsite training locations with daytime hours and may require evening hours and the potential for weekend hours.  The staff may be required to travel to other sites outside of the metropolitan area throughout the week. 
You Have: 

  • 5 years' experience in imaging, installing computer equipment and managing teams of technical staff
  • Must be able to unpack/re-pack, move, and install pallets of IT equipment with each item weighing up to 50 pounds with no restrictions
  • Must have personal transportation available during work hours     
  • Will need to consistently traverse around the site campus transporting equipment to various office buildings and frequently stoop, crouch, and reach to setup/remove computers/pull cords under desks and in server closets
  • Will frequently need to be able to push carts carrying equipment
  • Experience with hardware and software support, troubleshooting, system imaging, hardware break-fix support (i.e. laptops, desktops, and printers), refresh, upgrade, and deployment projects as well as excellent customer service skills
  • Experience with conducting routine system administration tasks and logging data in system admin logs
  • Experience with maintaining troubleshooting a wide variety of systems and networks, including high availability systems
  • Knowledge of debugging protocols and processes and the ability to work independently while providing excellent customer service
  • Bachelor's degree in computer science, Information System, Information Technology, or Equivalent and 5 total years of experience; or 13 total years of experience in lieu of a degree

Nice If You Have: 

  • Experience with the ServiceNow ticketing system a plus
  • Experience with the VA
  • Public Trust clearance
  • Experience with Microsoft windows desktop deployments
  • Experience as IT helpdesk Tier 1 or 2

Apply