Remote Windows System Administrator Jobs in Madison, WI

Introduction
Lend your technical knowledge and skills support and maintain an array of systems and cloud-based solutions that support Wisconsin's workforce. Apply now to join our team in the Bureau of Information Technology Services as an IT Cloud/System Administrator!
The Department of Workforce Development (DWD) offers interesting and meaningful work with an employee-friendly and inclusive work environment, work-life balance, a casual office environment, flexibility, and many opportunities to grow your skills. Apply now to find out why there's so much to love about working for Wisconsin .
The person hired into this position may request to work the majority of their work hours remotely and will be required to report occasionally to our downtown Madison location ( 201 E. Washington Ave. ).
This recruitment may be used to fill future similar vacancies (permanent, project or Limited Term).
Position Summary
Key responsibilities of the IT Cloud/System Administrator position include:

• Support infrastructure, server application, web-based & third-party applications, identity management, muti-factor solutions, security principles and Cloud technologies used at the agency.
• Interact with various teams including application development, security, workstation support and operations in the support of software used by DWD divisions and partners.
• Collaborate with the Department of Administration/Division of Enterprise Technology technical resources on enterprise services and project activity.
• Provide guidance on IT technical issues and make recommendations to management related to the procurement of new software and technology.
• Provide representation on enterprise-wide committees and interagency work groups and has the responsibility for implementing and managing the technical infrastructure.

This position has access to Federal Tax Information.
To learn more, please review the full position description .
Salary Information
Starting pay is between $93,600 and $108,160 per year, depending on qualifications, plus an exemplary benefits package :

• Generous paid time off , including at least 3 1/2 weeks of vacation/personal time, nine paid holidays, and ample sick time that rolls over each year with no cap.
• Excellent and affordable health insurance options starting at $45/month for single and $111/month for family coverage.
• Other great insurance options (dental, vision, life, and more).
• A top-notch retirement program and optional tax advantaged 457 retirement savings plan.
• A Well Wisconsin program, offering wellness tools and rewards to employees and spouses.
• A free and confidential employee assistance program that offers employees and their household members tools, resources, and professional consultation services.

Use this Total Rewards Calculator to see an estimate of the total value of our competitive benefits package!
The classification title for this position is IS Technical Services Specialist (schedule 07, range 33). A 12-month probationary period will be required. This position is considered exempt under the Fair Labor Standards Act.
Pay will be set in accordance with the State Compensation Plan in effect at the time of appointment. Starting pay may vary for current state employees.
Job Details
Remote work: Employees with approved remote and hybrid-remote work arrangements are generally expected to work within the state of Wisconsin. High-speed internet access is required to meet the needs of remote work. Remote work options are subject to change.
Criminal histories: We also consider all qualified applicants with criminal histories, consistent with applicable federal, state and local law. Finalists for this position may be required to allow DWD to conduct a background check or other checks to determine whether the circumstances of any conviction may be related to the job being filled. For positions with access to sensitive federal tax information, FBI fingerprinting may also be required.
Eligibility to work in United States: Applicants must be legally entitled to work in the United States (i.e. a US citizen or national or a lawful permanent resident) at the time of appointment. DWD does not sponsor visas and is not an eligible OPT employer for those with F1 visas. This is not a contract position. Any appointment made will be contingent on the applicant completing the I-9 upon hire.
Qualifications
The qualifications listed below will be evaluated in the first step of the selection process and should be clearly described in your resume/letter of qualifications.
You need to have the following experience:

• Installing, supporting, and maintaining software (such as Microsoft technologies, third-party software, etc.).
• Supporting Windows OS Servers and IIS Web administration.
• Using Virtualization technologies (such as VMware, Azure, etc.).

It would be nice to have experience supporting:

• Scripting technologies (such as PowerShell, Python, Bash, etc.).
• Microsoft 365 technologies (such as TEAMS, Intune, etc.).
• Infrastructure as Code (IaC) deployment technologies (such as Terraform, Azure DevOps, etc.).
• Cloud computing services (such as SaaS, PaaS, IaaS, etc.).
• Identity & Access Management (such as Microsoft AD, Entra ID, Multi-Factor, etc.).
• Network and end-point security (such as firewalls, MS Defender, etc.).

Additional qualifications may be evaluated in subsequent steps of the selection process.
How To Apply
Note: If you are viewing this posting on an external site, please visit Wisc.Jobs (search 21615) to complete your application.
To apply, click "Apply for Job" to start the application process. That will prompt you to access your existing account or create a new account. You will be asked to attach a resume and a letter of qualifications as part of the application process. Please review this additional guidance on developing your resume and letter of qualifications (including a template) as you prepare to apply.
Please see the Frequently Asked Questions for general Wisc.Jobs user information and technical assistance.

• Technical issues: if you encounter issues submitting your on-line application (e.g. signing in or uploading a resume), please email the Wisc.Jobs Help Desk at wiscjobs@wisconsin.gov or call (608) 267-1012 (Monday - Friday, 7:45am - 4:30pm).
• Position questions: if you have questions about the position or this recruitment (e.g. projected start date, skills needed, etc.), please email Lisa at LKBJobs@dwd.wisconsin.gov or call (608) 266-9310.

Please note that once you submit your application, you will not be able to update your materials.
What happens next? A panel will review your application materials to determine your eligibility for further consideration in the selection process. The most qualified applicants will be invited to participate in the next step of the selection process, which is typically a virtual interview.
DWD values a diverse workforce and is an equal opportunity and affirmative action employer. Veterans, women, people of color, LGBTQIA+, and people with disabilities are encouraged to apply. We provide reasonable accommodations to applicants and employees with disabilities.
The State of Wisconsin offers a special program for qualified veterans with a 30% or greater service-connected disability. If you are a qualified veteran, please visit the Veterans Employment page for application instructions to be considered for the Veterans Non-Competitive Appointment program.
Deadline to Apply
Application materials must be submitted by 11:59 PM (central standard time) on Monday, August 31, 2026.