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Remote Windows Systems Engineer Jobs in Chicago, IL

Automationtechies

Automation & Controls Engineer

Chicago, IL · On-site +1

$86K - $113K/yr

Hybrid/Remote Possible near Chicago, IL A reputable Systems Integrator located northwest of Chicago ... General IT and troubleshooting skills (Windows, Networks, Software & Hardware) * Ability ...

Talent Solutions Group Inc

Be Seen First

Senior Backend TypeScript Engineer - Node.js / GraphQL

Chicago, IL · Remote

$100K - $180K/yr

Distributed systems * Angular * C/C++ * Windows, Linux and macOS development environments * CI/CD ... Location Remote within the United States Chicago-area candidates are preferred but not required

Anomalix

Remote Consulting Engineer

Chicago, IL · On-site +1

Remote - Work from home - 75% travel to client site Status: Contract; Contract-to-hire; Full time ... Troubleshoot customer systems and work with software engineering staff to resolve problems ...

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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

See Chicago, IL salary details

$11

$52

$77

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

As of Aug 26, 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 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?

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 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 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
Infographic showing various Remote Windows Systems Engineer job openings in Chicago, IL as of June 2026, with employment types broken down into 100% Full Time. Highlights an 33% In-person, and 67% Remote job distribution, with an average salary of $110,011 per year, or $52.9 per hour.

Search Systems Engineer - Expert - AI Trainer

Chicago, IL • Remote

Mercor
See more jobs at Mercorexternal

$80 - $150/hr

Full-time

Posted 16 days ago

Job description

About the job

Mercor connects elite creative and technical talent with leading AI research labs. Headquartered in San Francisco, our investors include Benchmark, General Catalyst, Peter Thiel, Adam D'Angelo, Larry Summers, and Jack Dorsey.

Position: Software Engineer — Agentic Search Systems
Type: Contract
Compensation: $80–$150/hour
Location: Remote

Role Responsibilities

  • Evaluate the accuracy and depth of AI-generated content in search systems to strengthen reasoning and rigor in model outputs.
  • Develop and optimize systems related to agentic search for improved performance and reliability.
  • Scale data infrastructure to support modern search systems and enhance retrieval capabilities.
  • Collaborate with AI research teams to quantify impact and improvements in search systems.
  • Work independently and asynchronously to meet deadlines while improving AI model performance.

Qualifications

Must-Have

  • Experience shipping production search systems.
  • Ownership of relevance or retrieval on systems used by real users.
  • Ability to quantify impact and improvements in search systems.
  • Experience building systems related to agentic search.
  • Experience scaling data infrastructure for search systems.

Interview Process

  • 25 mins conversational interview. No coding, no take-home.
  • Follow-up with a paid 30-minute live conversation if interview stands out; $200 for your time.

Application Process (Takes 20–30 mins to complete)

  • Upload resume
  • AI interview based on your resume
  • Submit form

Resources & Support

  • For details about the interview process and platform information, please check: https://talent.docs.mercor.com/welcome
  • For any help or support, reach out to: support@mercor.com

PS: Our team reviews applications daily. Please complete your AI interview and application steps to be considered for this opportunity.


#hiringmercor