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Flex Time Remote Windows System Administrator Jobs in Chicago, IL

Shure

Senior Systems Administrator

Niles, IL · On-site +1

$86.50K - $117.10K/yr

This role will lead key functions including Windows and Linux administration, SAN management, and ... Focus on optimizing system performance, scalability, and security across all platforms. * Manage ...

Auria

Systems Engineer

Chicago, IL · Remote

$95K - $130K/yr

Remote Job Id: 13690-CPAW # of Openings: 1 Auria Innovations is seeking a talented Systems Engineer ... including Flex Time 11 paid days off: 6 fixed company holidays plus 5 floating holidays 401(k) ...

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Flex Time Remote Windows System Administrator information

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$55.6K

$98.8K

$134.4K

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

As of May 28, 2026, the average yearly pay for flex time remote windows system administrator in Chicago, IL is $98,849.00, according to ZipRecruiter salary data. Most workers in this role earn between $81,400.00 and $113,800.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a Flex Time Remote Windows System Administrator, and why are they important?

To thrive as a Flex Time Remote Windows System Administrator, you need strong expertise in Windows server administration, Active Directory management, and network troubleshooting, typically backed by a relevant IT degree or certifications such as CompTIA, MCSA, or MCSE. Familiarity with remote management tools (like PowerShell, RDP, and SCCM), virtualization platforms, and security protocols is essential. Exceptional problem-solving, time management, and clear communication skills help you efficiently support users and coordinate with distributed teams. These abilities ensure reliable system performance, secure operations, and productive collaboration in flexible, remote work environments.

What are some unique challenges faced by Flex Time Remote Windows System Administrators, and how can they be addressed?

Flex Time Remote Windows System Administrators often encounter challenges related to managing system updates, troubleshooting, and maintaining security across distributed environments. Working flexibly and remotely means coordinating with teams in different time zones and ensuring clear communication when resolving issues. To address these challenges, it's important to establish strong documentation practices, use robust remote monitoring tools, and maintain regular check-ins with team members to stay aligned on priorities and incident responses.

What is a Flex Time Remote Windows System Administrator?

A Flex Time Remote Windows System Administrator is an IT professional responsible for managing, maintaining, and troubleshooting Windows-based servers and systems, while working remotely with flexible working hours. This role involves tasks such as system updates, security monitoring, user account management, and ensuring system reliability. Flex time means the administrator can set their own work schedule within agreed parameters, rather than adhering to standard office hours. This setup is ideal for those who need adaptability in their work-life balance while supporting business IT operations.

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

AspectFlex Time Remote Windows System AdministratorFlex Time Remote Network Administrator
CertificationsMicrosoft Certified: Windows Server, CompTIA Network+Cisco CCNA, CompTIA Network+
Work EnvironmentManaging Windows servers, Active Directory, and system security remotelyConfiguring and maintaining network infrastructure, routers, switches remotely
Industry UsageIT services, enterprise environments, cloud providersTelecommunications, enterprise networks, data centers

Both roles often require similar certifications and work remotely in IT environments. The main difference is that the Windows System Administrator focuses on managing Windows servers and related systems, while the Network Administrator handles network infrastructure and connectivity. Your choice depends on whether you prefer working with server management or network hardware and configurations.

What are popular job titles related to Flex Time Remote Windows System Administrator jobs in Chicago, IL? For Flex Time Remote Windows System Administrator jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Flex Time Remote Windows System Administrator jobs in Chicago, IL look for? The top searched job categories for Flex Time Remote Windows System Administrator jobs in Chicago, IL are:
Flex Time Remote Windows System Administrator jobs near you
System Administrator

System Administrator

MatchPoint Solutions

Chicago Heights, IL • Remote

Other

This job post has expired today. Applications are no longer accepted.

Job description

MatchPoint Solutions is a fast-growing, young, energetic global IT-Engineering services company with clients across the US. We provide technology solutions to various clients like Uber, Robinhood, Netflix, Airbnb, Google, Sephora, and more! More recently, we have expanded to working internationally in Canada, China, Ireland, UK, Brazil, and India. Through our culture of innovation, we inspire, build, and deliver business results, from idea to outcome. We keep our clients on the cutting edge of the latest technologies and provide solutions by using industry-specific best practices and expertise.
We are excited to be continuously expanding our team. If you are interested in this position, please send over your updated resume. We look forward to hearing from you!
Title: System Administrator (Contract)
Location: 100% Remote (USA Only)
Shift: 2nd or 3rd Shift (Evening/Night)
Duration: Contract
Rate: $ 30 - 35/hr
We are seeking a System Administrator to support and maintain IT infrastructure in a fully remote environment. The ideal candidate will be responsible for monitoring, troubleshooting, and ensuring the stability and security of systems during off-hours operations.
Key Responsibilities
Monitor system performance, servers, and network infrastructure during assigned shift
Perform routine maintenance, updates, and patch management
Troubleshoot and resolve system, server, and network issues
Manage user accounts, permissions, and access controls
Respond to incidents, alerts, and service requests in a timely manner
Support backup and recovery operations
Maintain system documentation and update logs
Collaborate with cross-functional IT teams for issue resolution
MatchPoint Solutions provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.
This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

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