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Remote Windows System Administrator Jobs in Milwaukee, WI

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Remote Insurance Sales Associate

Milwaukee, WI · Remote

$50K - $120K/yr

Must have a cell phone & computer or laptop with a camera that operates on the Windows system ... Remote, work-from-home position, responsibilities include working over the phone and Zoom to assist ...

Everlight Solar

Salesforce Administrator

Milwaukee, WI · Remote

$80K - $100K/yr

This will be a full-time, work-from-home "remote" position. Must own a Mac computer and be fluent ... systems and processes Requirements: * Minimum two years of experience as a Salesforce.com ...

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Speech-Language Pathologist

Milwaukee, WI · Remote

$40 - $54/hr

100% remote | W2 employment | $40 - $54/hour | Flexible Scheduling (It is required to hold a state ... Our clinician-built AI assistant, Scout, dramatically cuts documentation time and admin tasks ...

Ascension

Medical Staff Services Manager

Glendale, WI · Remote

Remote Department: Medical Affairs Admin Schedule: Full-Time | Day Shift How you'll make an impact ... Where purpose meets opportunity Ascension is a leading nonprofit Catholic health system with a ...

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All JobsWindows System Administrator JobsRemote Windows System Administrator JobsRemote Windows System Administrator Jobs in Milwaukee, WI

Remote Windows System Administrator information

See Milwaukee, WI salary details

$53.2K

$94.5K

$128.6K

How much do remote windows system administrator jobs pay per year?

As of Aug 7, 2026, the average yearly pay for remote windows system administrator in Milwaukee, WI is $94,541.00, according to ZipRecruiter salary data. Most workers in this role earn between $77,800.00 and $108,900.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a remote Windows system administrator?

To thrive as a Remote Windows System Administrator, you need expertise in Windows Server administration, Active Directory, network protocols, and typically a degree in IT or related certifications like Microsoft Certified: Windows Server or Azure Administrator. Familiarity with tools such as PowerShell, Remote Desktop Services, VMware, and monitoring platforms is essential for managing and troubleshooting systems remotely. Excellent problem-solving, communication, and time-management skills help you to efficiently address issues and collaborate with distributed teams. These competencies ensure system reliability, security, and fast resolution of technical challenges in a remote environment.

What is a remote Windows system administrator?

A Remote Windows System Administrator is an IT professional responsible for managing, configuring, and maintaining Windows-based servers and systems from a remote location. Their duties include monitoring system performance, applying updates and patches, troubleshooting technical issues, and ensuring the security and reliability of Windows environments across an organization. They often use remote access tools to perform their tasks, helping organizations maintain efficient and secure IT operations without being physically present on-site.

What are some common challenges faced by remote Windows system administrators and how can they be addressed?

Remote Windows System Administrators often face challenges such as ensuring secure remote access, coordinating with geographically dispersed teams, and promptly resolving issues without on-site presence. To address these, effective communication tools, robust security protocols (like VPNs and multi-factor authentication), and proactive monitoring solutions are essential. Building strong documentation practices and maintaining regular updates with team members can also help manage tasks efficiently and ensure smooth operations.

What is the difference between Remote Windows System Administrator vs Remote Network Administrator?

AspectRemote Windows System AdministratorRemote Network Administrator
CertificationsMicrosoft Certified: Windows Server, CompTIA Network+Cisco CCNA, CompTIA Network+
Work EnvironmentManaging Windows servers, Active Directory, and server infrastructureManaging network hardware, routers, switches, and network security
Employer & Industry UsageIT departments across various industries focusing on Windows environmentsOrganizations needing network infrastructure management across industries

Remote Windows System Administrators primarily focus on managing Windows server environments, Active Directory, and related infrastructure. In contrast, Remote Network Administrators concentrate on network hardware, routing, switching, and network security. While both roles require networking certifications like CompTIA Network+ or Cisco CCNA, their daily tasks and focus areas differ significantly, catering to different aspects of IT infrastructure management.

What are popular job titles related to Remote Windows System Administrator jobs in Milwaukee, WI? For Remote Windows System Administrator jobs in Milwaukee, WI, the most frequently searched job titles are:
What job categories do people searching Remote Windows System Administrator jobs in Milwaukee, WI look for? The top searched job categories for Remote Windows System Administrator jobs in Milwaukee, WI are:
What cities near Milwaukee, WI are hiring for Remote Windows System Administrator jobs? Cities near Milwaukee, WI with the most Remote Windows System Administrator job openings:
Remote Windows System Administrator jobs near you
Infographic showing various Remote Windows System Administrator job openings in Milwaukee, WI as of August 2026, with employment types broken down into 1% As Needed, 83% Full Time, 13% Part Time, and 3% Contract. Highlights an 92% Physical, 2% Hybrid, and 6% Remote job distribution, with an average salary of $94,541 per year, or $45.5 per hour.

IT Cloud & Hosting System Administrator

Innio

Waukesha, WI • On-site, Remote

Other

Re-posted 7 days ago

Job description

About Us:

By combining a rich legacy in the power and gas compression space with pioneering technology, INNIO brings our customers affordable, reliable, and sustainable energy solutions for today-and tomorrow. We are helping to meet today's energy needs with 64 GW of installed capacity and 48,000 of our powerful Jenbacher and Waukesha engines, which can be found in more than 100 countries. And, by harnessing our history of energy industry first along with the power of digital innovation, we will continue to deliver for the future. It's time to take engines to a place no one else can. Welcome to the world of Innovation and Inspiration. Welcome to INNIO!

Location:

This is a hybrid remote position, ideally location is near Waukesha WI.

Essential Responsibilities:

  • Contribute to the administration, operation, and optimization of cloud environments (AWS, Azure) and on-premises IT infrastructure
  • Support modern hosting models, including serverless architectures and platform-based deployments
  • Support the administration and maintenance of VMware vSphere and ESXi host environments to ensure stable and efficient virtual infrastructure operations
  • Assist in the development and operation of CI/CD pipelines and Infrastructure-as-Code (Terraform)
  • Support identity and access management (IAM) for both cloud and on-premises environments
  • Contribute to the administration and support of data analytics and data platform services (e.g., Tableau, Power BI)
  • Participate in implementing and monitoring cybersecurity measures, including automation of routine operational tasks
  • Support and ensure backup, disaster recovery, and business continuity concepts
  • Troubleshoot infrastructure and cloud-related issues and provide 2nd level support
  • Collaborate closely with global IT teams and stakeholders to deliver scalable, stable, and secure solutions
  • Contribute to documentation and continuous improvement of operational processes

Qualification Requirements:

  • Completed IT education (apprenticeship, technical degree) or comparable professional experience
  • Hands-on experience in cloud environments (Azure and/or AWS).
  • High Experience with VMware vSphere and ESXi host administration in virtualized infrastructure environments is an advantage.
  • Basic to solid understanding of infrastructure automation (e.g., Terraform) and CI/CD concepts.
  • Experience or interest in serverless architecture and modern cloud hosting. Familiarity with IAM concepts across cloud and on-prem systems.
  • Understanding of backup/recovery, monitoring, and operational best practices in the IT Infrastructure environment.
  • Knowledge of data platforms or analytics tools is a plus.
  • Strong analytical and troubleshooting skills with a structured working approach Proactive, solution-oriented mindset and ability to work in an international environment.
Employment Type: Experienced

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