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Remote Windows Systems Engineer Jobs in Chicago, IL

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 ...

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 ...

Senior Systems Engineer

Chicago, IL · Remote

$107K - $146K/yr

As our next Senior Systems Engineer , you won't just be maintaining our corporate infrastructure ... stipend for remote workers, and a four-week paid sabbatical with bonus after five years ...

Senior Systems Engineer

Chicago, IL · On-site +1

$113K - $138K/yr

As our next Senior Systems Engineer , you won't just be maintaining our corporate infrastructure ... stipend for remote workers, and a four-week paid sabbatical with bonus after five years ...

Senior Systems Engineer

Downers Grove, IL · On-site +1

$104K - $142K/yr

The Senior Systems Engineer is responsible for designing, implementing, and maintaining components of the internal technology architecture. By combining deep technical expertise and exceptional ...

The Cloud and Systems Engineer is a hands-on technical role responsible for designing, implementing ... Proficiency with Windows Server (2012-2022) and Windows 10/11. * Experience with virtualization ...

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Remote Windows Systems Engineer information

See Chicago, IL salary details

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

As of Jun 17, 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 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:
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 100% Remote job distribution, with an average salary of $110,011 per year, or $52.9 per hour.
Senior Systems Engineer

Senior Systems Engineer

Akuna Capital

Chicago, IL • On-site, Remote

$145K/yr

Other

Medical, Dental, Vision, Retirement, PTO

Posted 18 hours ago


Job description

About Akuna: 

Akuna Capital is an innovative trading firm with a strong focus on collaboration, cutting-edge technology, data driven solutions, and automation. We specialize in providing liquidity as an options market-maker - meaning we are committed to providing competitive quotes that we are willing to both buy and sell. To do this successfully, we design and implement our own low latency technologies, trading strategies, and mathematical models.  

Our Founding Partners first conceptualized Akuna in their hometown of Sydney. They opened the firm's first office in 2011 in the heart of the derivatives industry and the options capital of the world - Chicago. Today, Akuna is proud to operate from additional offices in Sydney, Shanghai, London and Singapore. 

What you will do as a Senior Systems Engineer at Akuna: 

We are looking for a versatile and driven Senior Systems Engineer to join our Engineering team in building a best-in-class trading infrastructure. In this role, you'll tackle complex, large-scale technical challenges and play a key role in the architecture and design of low latency platforms, building automated deployments and tooling, and optimizing and maintaining of our high-performance global trading environment. The ideal candidate will be self-motivated, proactive, and able to take ownership of projects and problemswith minimal oversight. In this role, you will: 

  • Analyze complex technical problems and collaborate on designing solutions for Akuna's global Infrastructure platform 
  • Drive projects and solutions to completion in a fast-paced environment 
  • Design, develop and maintain orchestration and configuration solutions 
  • Collaborate with developers and other infrastructure engineers to research new products and techniques that drive innovation and improve efficiency and performance in the environment 
  • Architect and maintain multi-vendor, tier-based storage solutions 
  • Build out a test automation framework for systems performance testing and tuning 
  • Create and institute process enforcement across environments 
  • Create tools that assist teams to optimize the available infrastructure 
  • Develop and maintain comprehensive technical documentation, including system configurations, procedures, and troubleshooting guides 
  • Lead knowledge transfer sessions and mentor team members to ensure continuity and operational excellence 
  • Collaborate with cross-functional teams to optimize system performance, security, and reliability 

Qualities that make great candidates: 

  • Degree in Computer Science, Information Systems, or a related field 
  • 5-7 years of systems engineering experience (trading industry experience a strong plus) 
  • Advanced Linux knowledge including, but not limited to, kernel bypass, kernel tuning, and customizing kernels 
  • Deep understanding of virtualization and containerization technologies 
  • Extensive experience with a variety of Linux distributions (RedHat, Ubuntu, etc.) 
  • Deep understanding of system monitoring and configuration management tools (Ansible, Foreman, Prometheus and Icinga/Nagios) 
  • Proficiency in scripting and using automation and orchestration tools such as Python and Bash 
  • Expertise in troubleshooting multicast and TCP related performance issues 
  • Experience automating daily software and hardware related tasks 
  • Demonstrated ability to lead large technical projects 
  • Experience with automating infrastructure builds, such as Preseed, NetBoot, Anaconda, Kickstart and Ansible customization 
  • Familiarity with git or a similar version control tool 
  • Working knowledge of database systems, including PostgreSQL and MySQL 
  • Familiarity with Windows environments is a plus  
  • Experience working with SOAP and REST APIs a plus 
  • The ability to react quickly and accurately to rapidly changing market conditions, including the ability to quickly and accurately respond and/or solve math and coding problems are essential functions of the role
  • This role is open to hybrid and fully remote candidates

 In addition to technical skillsets, Akuna values the unique perspectives people can bring to the table to collaboratively solve complex problems and drive Akuna forward. We want everyone to feel empowered to apply. We welcome your application and encourage you to take the first steps toward your future with us!

In accordance with Illinois Equal Pay Act, the minimum base salary starts at $145,000. Exact compensation offered may vary based on many factors including, but not limited to, the candidate's experience, qualifications, and skill set. This role is also eligible for a discretionary performance bonus as part of the total compensation package and includes a comprehensive benefits package that may encompass employer-paid medical, dental, vision, retirement contributions, paid time off, and other benefits. The minimum base salary herein was determined in good faith by Akuna Capital LLC.