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Remote Windows Systems Engineer Jobs in Chicago, IL

UpStream Global Services

Systems Engineer

Chicago, IL · Remote

The System Engineer will be responsible for designing, implementing, maintaining, and optimizing ... Strong knowledge of Windows and Linux server environments. Experience with virtualization ...

UpStream Global Services

Systems Engineer

Chicago, IL · On-site +1

The System Engineer will be responsible for designing, implementing, maintaining, and optimizing ... Strong knowledge of Windows and Linux server environments. Experience with virtualization ...

Akuna Capital

Senior Systems Engineer

Chicago, IL · On-site +1

$145K/yr

Familiarity with Windows environments is a plus * Experience working with SOAP and REST APIs a plus ... This role is open to hybrid and fully remote candidates In addition to technical skillsets, Akuna ...

Akuna Capital

Systems Engineer

Chicago, IL · On-site +1

$120K/yr

What you will do as a Systems Engineer at Akuna: We are looking for a versatile and driven Systems ... This role is open to hybrid and fully remote candidates In addition to technical skillsets, Akuna ...

Humana

Senior Systems Engineer

Chicago, IL · Remote

$107K - $147K/yr

Systems software engineering/programming is a specialized area of software engineering/programming ... While this is a remote position, occasional travel to Humana's offices for training or meetings may ...

Humana

Senior Systems Engineer

Chicago, IL · Remote

$107K - $147K/yr

Systems software engineering/programming is a specialized area of software engineering/programming ... While this is a remote position, occasional travel to Humana's offices for training or meetings may ...

Humana

Senior Systems Engineer

Chicago, IL · Remote

$107K - $147K/yr

Systems software engineering/programming is a specialized area of software engineering/programming ... While this is a remote position, occasional travel to Humana's offices for training or meetings may ...

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All JobsWindows Systems Engineer JobsRemote Windows Systems Engineer JobsRemote Windows Systems Engineer Jobs in Chicago, IL

Remote Windows Systems Engineer information

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How much do remote windows systems engineer jobs pay per hour?

As of Jul 13, 2026, the average hourly pay for remote windows systems engineer in Chicago, IL is $52.89, according to ZipRecruiter salary data. Most workers in this role earn between $41.83 and $63.41 per hour, depending on experience, location, and employer.

What are some common challenges faced by Remote Windows Systems Engineers, and how can they be effectively managed?

Remote Windows Systems Engineers often encounter challenges such as troubleshooting complex system issues without direct physical access, ensuring secure remote connectivity, and coordinating across distributed teams and time zones. Effective management of these challenges involves utilizing robust remote monitoring and management tools, maintaining clear and regular communication with colleagues, and following best practices for system security and documentation. Staying proactive with updates and leveraging collaboration platforms can significantly enhance productivity and reduce downtime.

What is the difference between Remote Windows Systems Engineer vs Remote Network Administrator?

AspectRemote Windows Systems EngineerRemote Network Administrator
CertificationsMicrosoft Certified: Windows Server, CompTIA Network+Cisco CCNA, CompTIA Network+
Work EnvironmentManaging Windows servers, troubleshooting OS issues, deploying updatesConfiguring and maintaining network infrastructure, monitoring network performance
Industry UsageIT, technology, enterprise environmentsIT, telecommunications, service providers
Search IntentFocus on Windows server management and supportFocus on network infrastructure and connectivity

The Remote Windows Systems Engineer primarily manages and supports Windows server environments, ensuring system stability and security. In contrast, the Remote Network Administrator focuses on maintaining network infrastructure, including routers, switches, and connectivity. While both roles require networking knowledge and certifications, their core responsibilities differ, with the Systems Engineer centered on Windows OS and server management, and the Network Administrator on network hardware and connectivity.

What does a Remote Windows Systems Engineer do?

A Remote Windows Systems Engineer is responsible for designing, implementing, and maintaining Windows-based server environments from a remote location. They manage tasks such as installing updates, configuring security settings, troubleshooting technical issues, and ensuring system performance and reliability. These engineers often work with cloud platforms, virtualization technologies, and collaborate with IT teams to support business operations. Their remote role allows them to provide support and maintenance without being physically present on-site.

What are the key skills and qualifications needed to thrive as a Remote Windows Systems Engineer, and why are they important?

To thrive as a Remote Windows Systems Engineer, you need expertise in Windows Server administration, system troubleshooting, and network protocols, often backed by a degree in IT or computer science and certifications like Microsoft Certified: Windows Server Hybrid Administrator Associate. Familiarity with tools such as Active Directory, PowerShell, virtualization platforms, and remote management software is essential. Strong problem-solving abilities, effective communication, and self-motivation are critical soft skills for managing systems and collaborating virtually. These skills ensure secure, reliable system operations and efficient remote support in distributed IT environments.
What are the most commonly searched types of Windows Systems Engineer jobs in Chicago, IL? The most popular types of Windows Systems Engineer jobs in Chicago, IL are:
What are popular job titles related to Remote Windows Systems Engineer jobs in Chicago, IL? For Remote Windows Systems Engineer jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Windows Systems Engineer jobs in Chicago, IL look for? The top searched job categories for Remote Windows Systems Engineer jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Windows Systems Engineer jobs? Cities near Chicago, IL with the most Remote Windows Systems Engineer job openings:
Remote Windows Systems Engineer jobs near you
Systems Engineer - Windows

Systems Engineer - Windows

Hudson River Trading

Chicago, IL • On-site, Remote

Other

Posted 20 days ago

Job description

Hudson River Trading (HRT) is seeking a Windows Systems Engineer to join our Enterprise Engineering team. In this role, you will help scale HRT's global hybrid Windows deployment and develop automation, configuration-as-code, and infrastructure-as-code solutions to seamlessly manage fleets of top-of-the-line user endpoints, mission critical servers, cloud infrastructure, and secure remote computing environments around the world. You will apply configuration-as-code practices to reduce operational overhead, build PowerShell-based systems that improve platform stability and resilience, and enhance the reliability of our Windows platform by designing and implementing automation that identifies and resolves technical inefficiencies across on-premises and Azure infrastructure.

The ideal candidate is a Microsoft-based technology engineer and eager problem solver who is comfortable working in a fast-paced environment. Terrific communication and collaboration skills, as well as a positive attitude towards team members and internal customers, are crucial to success within this role. 

Responsibilities

  • Leverage configuration-as-code paradigms to reduce the operational overhead of managing Windows infrastructure
  • Use infrastructure-as-code to consistently configure Microsoft Azure resources
  • Develop PowerShell-based systems to automate operational tasks and enhance the reliability of the Windows platform
  • Leverage automation to identify and remediate technical inefficiencies across Windows endpoints, Windows infrastructure, and Microsoft Azure resources
  • Participate in ongoing engineering, maintenance, and support efforts to improve the Windows environment

Qualifications

  • 10+ years of experience as a Microsoft-based technology engineer
  • Experience using Ansible (or similar configuration-as-code tool) to manage a fleet of Windows devices
  • Proven ability to provision Microsoft Azure resources with Terraform
  • Proficiency with Microsoft Graph API development
  • Experience developing scripts and tools using PowerShell
  • Familiarity with Microsoft Intune, Autopilot, Entra ID, and Active Directory
  • A general design approach that incorporates security best practices, business continuity, high availability, and scalability
  • A self-motivated and driven work ethic

The estimated base salary range for this position is 150,000 to 250,000 USD per year (or local equivalent). The base pay offered may vary depending on multiple individualized factors, including location, job-related knowledge, skills, and experience. This role will also be eligible for discretionary performance-based bonuses and a competitive benefits package.

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