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Entry Level Windows Systems Administrator Jobs in Milwaukee, WI

Robert Half

Systems Administrator

Milwaukee, WI · On-site

$38 - $44/hr

We are looking for a Systems Administrator to support and strengthen a dynamic IT environment in ... Maintain and support Windows server environments, including core services that keep business ...

River Run Computers

Systems Administrator

Milwaukee, WI · On-site

Windows Desktop Administration * Windows Server Administration * Mastery of Basic TCP/IP Skills ... Every Systems Administrator will be expected to hold at minimum a basic competency certificate in ...

River Run Computers Inc

Systems Administrator

Glendale, WI · On-site

$55K - $90K/yr

Windows Desktop Administration * Windows Server Administration * Mastery of Basic TCP/IP Skills ... Every Systems Administrator will be expected to hold at minimum a basic competency certificate in ...

No Limit Technology

System Administrator

New Berlin, WI · Hybrid

... IT systems while supporting a growing internal development team and scaling business needs. Responsibilities Infrastructure & Operations Administer and maintain Windows Server environments (AD, DNS ...

Tanis Brush

IT Systems Administrator

Delafield, WI · On-site

$85 - $120/hr

The role independently administers Microsoft 365, Active Directory, Windows Server and Hyper‑V ... The Systems Administrator evaluates technical and business requirements, compares alternative ...

LDV, Inc.

Entry Level Builder

Burlington, WI · On-site

$19 - $22.50/hr

Installation of flooring, walls, ceilings, cabinets, shelves, doors, windows, and trim. * Cutting ... Installing AC/DC wiring systems. Requirements Candidates should have these qualifications:

LDV, Inc.

Entry Level Builder

Burlington, WI · On-site

$19 - $22.50/hr

Installation of flooring, walls, ceilings, cabinets, shelves, doors, windows, and trim. * Cutting ... Installing AC/DC wiring systems. Requirements Candidates should have these qualifications:

LDV, Inc.

Entry Level Builder

Burlington, WI

$19 - $22.50/hr

Installation of flooring, walls, ceilings, cabinets, shelves, doors, windows, and trim. * Cutting ... Installing AC/DC wiring systems. Requirements Candidates should have these qualifications:

JX Enterprises, Inc

Sales Administrator

Hartland, WI · On-site

$21/hr

From entry-level opportunities to experienced roles, this position is tailored for motivated and ... Enter, maintain, and review information relevant to the sale of trucks into the business systems ...

JX Enterprises, Inc.

Sales Administrator

Hartland, WI · On-site

$21 - $25/hr

From entry-level opportunities to experienced roles, this position is tailored for motivated and ... Enter, maintain, and review information relevant to the sale of trucks into the business systems ...

JX Enterprises Inc

Sales Administrator

Hartland, WI · On-site

$21 - $25/hr

From entry-level opportunities to experienced roles, this position is tailored for motivated and ... Enter, maintain, and review information relevant to the sale of trucks into the business systems ...

TEKsystems

Systems Engineer

Kenosha, WI

$38 - $50/hr

Windows Server Administration * Active Directory * VMware * Systems Administration * Microsoft 365 ... It is unlawful in Massachusetts to require or administer a lie detector test as a condition of ...

MDAEdge

Network and Infrastructure Engineer

Racine, WI · On-site

... Administer Windows Server operating systems including Windows Server 2016, monitoring, troubleshooting, and parts swaps/repair. • Configure and manage DHCP, DNS, print servers, file shares, and ...

MDAEdge

Network and Infrastructure Engineer

Kenosha, WI · On-site

... Administer Windows Server operating systems including Windows Server 2016, monitoring, troubleshooting, and parts swaps/repair. • Configure and manage DHCP, DNS, print servers, file shares, and ...

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All JobsWindows Systems Administrator JobsEntry Level Windows Systems Administrator JobsEntry Level Windows Systems Administrator Jobs in Milwaukee, WI

Entry Level Windows Systems Administrator information

See Milwaukee, WI salary details

$53.2K

$94.5K

$128.6K

How much do entry level windows systems administrator jobs pay per year?

As of Aug 28, 2026, the average yearly pay for entry level windows systems 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 does an entry level Windows Systems Administrator do?

An Entry Level Windows Systems Administrator is responsible for assisting with the setup, configuration, and maintenance of Windows-based servers and workstations within an organization. Their duties often include monitoring system performance, installing updates, troubleshooting basic technical issues, and helping ensure the security of the IT environment. They usually work under the supervision of more experienced administrators and provide support to end-users as needed. This role is ideal for those starting a career in IT and looking to build foundational skills in system administration.

What are the key skills and qualifications needed to thrive as an entry level Windows Systems Administrator?

To excel as an Entry Level Windows Systems Administrator, a solid understanding of Windows operating systems, basic networking concepts, and troubleshooting skills—often supported by a relevant degree or coursework—is essential. Familiarity with Active Directory, PowerShell scripting, and foundational certifications like CompTIA A+ or Microsoft Certified: Windows Server Fundamentals is highly beneficial. Strong problem-solving abilities, attention to detail, and effective communication are standout soft skills for this role. These skills and qualifications are crucial for ensuring reliable system performance, quick issue resolution, and seamless collaboration within IT teams.

What are some common challenges faced by entry level Windows Systems Administrators during their first year on the job?

Entry level Windows Systems Administrators often encounter challenges such as learning to efficiently troubleshoot unfamiliar system errors, managing time while juggling multiple support tickets, and adapting to the organization's specific network and security protocols. Balancing day-to-day maintenance tasks with urgent support requests can be demanding, especially when prioritizing issues for minimal disruption. However, most teams foster a collaborative environment, so asking questions and seeking guidance from more experienced admins is encouraged and can help build confidence and technical proficiency.

What is the difference between Entry Level Windows Systems Administrator vs Network Support Technician?

AspectEntry Level Windows Systems AdministratorNetwork Support Technician
CertificationsCompTIA A+, Microsoft Certified: Windows Server FundamentalsCompTIA A+, Cisco CCNA
Work EnvironmentServer rooms, data centers, IT departmentsHelp desks, client sites, network operations centers
Primary ResponsibilitiesManaging Windows servers, user accounts, system updatesTroubleshooting network issues, configuring routers/switches

Entry Level Windows Systems Administrators focus on managing and maintaining Windows server environments, while Network Support Technicians primarily troubleshoot and support network infrastructure. Both roles require foundational certifications and are common entry points in IT, but they differ in daily tasks and work settings.

What are popular job titles related to Entry Level Windows Systems Administrator jobs in Milwaukee, WI?

For Entry Level Windows Systems Administrator jobs in Milwaukee, WI, the most frequently searched job titles are:

What job categories do people searching Entry Level Windows Systems Administrator jobs in Milwaukee, WI look for?

The top searched job categories for Entry Level Windows Systems Administrator jobs in Milwaukee, WI are:

What cities near Milwaukee, WI are hiring for Entry Level Windows Systems Administrator jobs?

Cities near Milwaukee, WI with the most Entry Level Windows Systems Administrator job openings:

Entry Level Windows Systems Administrator jobs near you
Infographic showing various Entry Level Windows Systems Administrator job openings in Milwaukee, WI as of August 2026, with employment types broken down into 85% Full Time, 9% Part Time, 5% Contract, and 1% Nights. Highlights an 89% Physical, 3% Hybrid, and 8% Remote job distribution, with an average salary of $94,541 per year, or $45.5 per hour.

Windows Systems Administrator (xin001_JN8T)

Xinnovit

Milwaukee, WI

Full-time

Re-posted 26 days ago

Job description

Company Description

Xinnovit is a global leader in technology consulting, outsourcing, and workforce management solutions.
Our mission is to enable our clients to become more agile and competitive with the help of innovative technologies. We empower our clients to respond faster and more intuitively to changing market dynamics.
The business environment is complex, often under significant constraints and pressures from various sources. We have the knowledge, experience and capabilities to provide our clients the tools they require to achieve better, faster and effective transformation that make them the leaders in their industry.
Our Goals Are:


To use our expertise to the benefit of our clients and partners through open communication and collaboration.
To ensure sustainable and profitable long-term growth.
To provide a return on investment to shareholders.
To promote employee development.

Job Description

MCSE certified

Strong Windows Server skills (Windows Server 2008 and 2012)

Strong Active Directory implementation and operation skills

Active Directory troubleshooting

Active Directory OU/GPO creation and testing

Windows Security

Windows Patching / Patch Automation

Windows Automation / Powershell

VMware v5 and v6 skills (vSphere hosts, vCenter, vROPs, SRM, VMware View, VCAC)

Team leadership

Strong communications skills

Additional Information

All your information will be kept confidential according to EEO guidelines.

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