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Windows Deployment Jobs in Wisconsin (NOW HIRING)

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 ...

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 ...

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 ...

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 ...

Strong PowerShell and Microsoft Graph automation experience, including scalable deployment and remediation patterns * Experience designing Windows Autopilot and modern device enrollment strategies

Help Desk - 2

Madison, WI · On-site

$20.25 - $27.25/hr

... Windows XP1 YrsProblem documentation and communication1 YrsGeneral understanding of LANDesk (for patch management, software deployment, inventory management an1 YrsActive Directory1 Yrs To apply ...

Senior Endpoint Engineer

La Crosse, WI · On-site

$75K - $112K/yr

Coordinate and validate endpoint deployments, updates, and remediation activities to ensure ... Develop and maintain technology roadmaps for Windows, MECM/SCCM, and related endpoint management ...

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Windows Deployment information

See Wisconsin salary details

$22

$32

$45

How much do windows deployment jobs pay per hour?

As of Jul 16, 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 roles?

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 replaced Windows deployment services?

Windows Deployment Services (WDS) has been largely replaced by Microsoft Endpoint Configuration Manager (formerly SCCM) for large-scale deployment and management of Windows images. Additionally, tools like Microsoft Deployment Toolkit (MDT) and Windows Autopilot are now commonly used for automated and cloud-based deployment processes, offering more flexible and modern solutions for IT professionals.

What is Windows deployment?

Windows deployment involves installing and configuring the Windows operating system across multiple computers, often using specialized tools like Windows Deployment Services (WDS) or Microsoft Deployment Toolkit (MDT). It requires knowledge of imaging, scripting, and network setup to efficiently roll out Windows in enterprise environments.

What is a Windows Deployment job?

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.

Is WDS still used?

Windows Deployment Services (WDS) is still used by IT professionals for network-based deployment of Windows operating systems. It remains a common tool for automating OS installations in enterprise environments, especially when combined with tools like MDT or SCCM. However, newer deployment methods and cloud-based solutions are increasingly being adopted alongside WDS.

What are the key skills and qualifications needed to thrive in the Windows Deployment position, and why are they important?

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 does a deployment technician do?

A deployment technician is responsible for installing, configuring, and maintaining operating systems, software, and hardware on computers and networks. They often work with tools like imaging software and may troubleshoot technical issues during deployment. The role requires technical skills, attention to detail, and knowledge of system configurations and network 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:
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Infographic showing various Windows Deployment job openings in Wisconsin as of July 2026, with employment types broken down into 90% Full Time, 6% Part Time, 1% Temporary, and 3% Contract. Highlights an 86% Physical, 3% Hybrid, and 11% Remote job distribution, with an average salary of $66,617 per year, or $32 per hour.
Systems Administrator - Windows Server + M365

Systems Administrator - Windows Server + M365

Flad Architects

Madison, WI • Hybrid

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 29 days ago


Job description

If you enjoy solving complex challenges in a collaborative environment that celebrates each person’s ideas, experience, and creativity, this might be the opportunity for you. Flad is a national architectural firm with ten offices, looking to hire a Systems Administrator to work in our Madison, WI office. This role assists in the configuration and maintenance of Flad’s system infrastructure, including application license servers, Windows servers, and escalations from the service desk. It also assists with Windows enterprise systems administration and on-premises Microsoft systems. Flad is a team of creative, intelligent, energetic people who help our clients tackle the issues that change people’s lives.


  • Maintain and manage Microsoft 365 services and related processes.
  • Perform system administration for all assigned systems, manage vendor relationships, and maintain the security and integrity of systems and backups.
  • Assist in managing system administration for infrastructure systems such as building security, Microsoft systems infrastructure, and software licensing systems.
  • Assist in the evaluation, research, and implementation of Windows server-based technologies.
  • Oversee the installation, configuration, testing, deployment, upgrading, management, and documentation of Windows server hardware, Hyper-V, and software configurations to maximize security, reliability, and minimize vulnerabilities.
  • Perform overall administration of Flad collaboration systems, such as Microsoft 365 email and account maintenance, Zoom, and Microsoft Teams.
  • Manage the installation, support and updates of software applications and Windows Server operating systems. Participate in technical support on troubleshooting problems and standard software applications.
  • Perform scheduled rotation of routine technical support duties (help desk and pager).

Technical Experience:

  • Minimum one year of relevant systems support experience required.
  • Minimum one year of experience with Microsoft Windows Server operating systems and Microsoft Windows 11 operating system required.
  • Experience with Microsoft Office applications and other similar standard office applications required. Familiarity with AutoCAD, Revit, and Adobe desktop publishing/design applications preferred.
  • Minimum one year of experience installing, configuring, and troubleshooting IP computing devices on a TCP/IP network required.
  • Experience with Powershell scripting, automation methods, InTune policies and GPOs required.
  • Experience with automated software deployment systems such as WSUS, PDQ Deploy, InTune, etc. preferred.

Other Skills:

  • Ability to communicate effectively (written and verbal) with clients, consultants, and team members.
  • Skilled at working well within a team environment, with people at all levels of an organization, while juggling multiple demands.
  • Strong attention to detail, excellent organizational and interpersonal skills, and flexibility in adjusting to shifting priorities and/or deadlines.
  • Ability to problem-solve and resolve client issues while providing a quality, personable experience.
  • Availability during Flad’s business hours of 8:00 a.m. to 5:00 p.m. is required. Must be able to work in the Madison office Tuesday through Thursday each week.

Education:

  • Minimum two-year technology degree required.

Flad offers a wide range of benefits, including: 

  • Health, dental, and vision insurance
  • Generous paid time off and paid holidays
  • Financial health and wellness benefits - retirement savings plan; fiduciary advisor; identity theft plan; Section 125 flexible benefits, including mass transit and parking; income protection – life insurance, short-term disability, long-term disability; Employee Assistance Program (EAP)
  • Continuing education and career development – internal programs; funds set aside for external programs, licensure and sustainability support, annual professional registration, and organization reimbursement
  • Hybrid work environment 

Flad Architects is an Equal Employment Opportunity employer. Flad will provide equal employment opportunities to all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.

If you need a reasonable accommodation to apply for a position, please contact Human Resources at 608-238-2661 or email us at humanresources@flad.com.