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Remote Windows Systems Engineer Jobs in Lake Forest, IL

AI Engineer - Remote

Chicago, IL ยท Remote

$80 - $120/hr

Remote Job Summary We are seeking experienced Senior Software Engineers to support an AI training ... Build deterministic verification systems and golden reference solutions. * Evaluate AI agents ...

AI Consulting Expert - Remote

Chicago, IL ยท Remote

$100 - $200/hr

... AI systems. In this role, you will evaluate, review, and refine AI-generated business content ... Prompt Engineering * AI Output Evaluation * Quality Assurance * Technical & Report Writing

Remote Job Summary We are seeking experienced Senior Software Engineers to support an AI training ... Build deterministic verification systems and golden reference solutions. * Evaluate AI agents ...

AI Software Engineer - Remote

Chicago, IL ยท Remote

$80 - $120/hr

Remote Job Summary We are seeking experienced Senior Software Engineers to support an AI training ... Build deterministic verification systems and golden reference solutions. * Evaluate AI agents ...

AI Cloud Engineer

Chicago, IL ยท Remote

$57.50 - $76.75/hr

... Windows environments, containerized workloads, and distributed cloud-based systems. * Excellent ... Chicago, IL (Remote) Industry: E-Commerce Company Size: What They Do: Our client offers a powerful ...

DevOps Engineer - Remote

Chicago, IL ยท Remote

$50 - $150/hr

Remote Job Overview We are seeking experienced DevOps Engineers to create and evaluate production-style infrastructure and automation tasks for next-generation AI systems. You will work on CI/CD ...

AI/ML Engineer - Remote

Chicago, IL ยท Remote

$200 - $350/hr

Remote Job Summary We are seeking an experienced AI/ML Engineer to build and deploy secure ... You will work with LLMs, RAG, prompt engineering, multi-agent systems, and cloud AI platforms to ...

Remote Job Summary We are seeking experienced Senior Software Engineers to support an AI training ... Build deterministic verification systems and golden reference solutions. * Evaluate AI agents ...

AI Cloud Engineer

Elk Grove Village, IL ยท Remote

$55 - $73.50/hr

Chicago, IL (Remote) Industry: E-Commerce Company Size: What They Do: Our client offers a powerful ... Linux and Windows environments, containerized workloads, and distributed cloud-based systems.

Showing results 41-60

Remote Windows Systems Engineer information

See Lake Forest, IL salary details

$10

$50

$74

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

As of Sep 8, 2026, the average hourly pay for remote windows systems engineer in Lake Forest, IL is $50.84, according to ZipRecruiter salary data. Most workers in this role earn between $40.24 and $60.91 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 Lake Forest, IL?

The most popular types of Windows Systems Engineer jobs in Lake Forest, IL are:

What cities near Lake Forest, IL are hiring for Remote Windows Systems Engineer jobs?

Cities near Lake Forest, IL with the most Remote Windows Systems Engineer job openings:

Technical Operations Analyst with Python, Electronic Trading Systems Preferred - Work From Home

Next Step Systems

Chicago, IL โ€ข On-site, Remote

Full-time

Medical, Dental, Vision, Life

Re-posted 17 hours ago


Key responsibilities

  • Oversee the operation and maintenance of trading systems to ensure continuity and stability in the production trading environment.

  • Develop automation tools to streamline operational processes and improve efficiency.

  • Triage, prioritize, and troubleshoot complex network and systems issues, including hardware and software problems.


Job description

Technical Operations Analyst with Python, Electronic Trading Systems Preferred - Work From Home
We are currently looking for a Technical Operations Analyst for a great opportunity. The company participates in a wide variety of marketplaces including global futures, equities, commodities, options, fixed income, and cryptocurrencies. Their culture emphasizes teamwork and focuses on continuous integration and test-driven development. This position is 100% Remote.
Technical Operations Analyst Responsibilities:
- Oversee the operation and maintenance of our trading systems, guaranteeing continuity and stability in our production trading environment.
- Develop automation tools to streamline operational processes, reducing overhead and enhancing efficiency.
- Triage, prioritize and troubleshoot complex network and systems issues, ranging from low-level hardware to in-house software applications.
- Work with development to improve the operational stability and functionality of existing and new trading systems.
- Coordinate, plan, and execute firm-wide changes within a global change management framework.
- Understand and account for the needs of all stakeholders.
- On call coverage in a team rotation.
- Support other key initiatives as the business dictates.
Technical Operations Analyst Qualifications:
- Need a bachelor's or associate degree, preferably in a technical area such as computer science or engineering.
- Exceptional communication and collaboration skills.
- Extremely proficient in Python development, including aspects of application requirements, design, implementation and deployment.
- A self-motivated personality with a passion for solving complex problems.
- Proficient in Linux.
- Strong organizational skills, ability to effectively plan and prioritize.
- Understanding of networking concepts such as DNS, HTTP, TCP/IP, UDP, multicast and related protocols.
- Can demonstrate a high level of initiative and the ability to quickly build trust with trading and technology.
Technical Operations Analyst Preferred Qualifications:
- Experience supporting electronic trading systems.
- Prior experience with Grafana or other data visualization tools.
- Familiarity with Atlassian suite of products (Confluence, Jira, Bitbucket).
- Experience with Active Directory, Windows Server and Windows 11.
- Understanding of cybersecurity principles and best practices in operational environments.
Benefits include medical, dental, vision, health savings account, life insurance policy, short-term/long-term disability insurance, employee assistance program, etc.
Keywords: Chicago IL Jobs, Technical Operations Analyst, Python, Linux, DNS, HTTP, TCP/IP, UDP, Multicasting, Grafana, Atlassian, Confluence, Jira, Bitbucket, Windows Server, Active Directory, Electronic Trading Systems, Trading, Financial, Chicago Recruiters, Information Technology Jobs, IT Jobs, Chicago Recruiting
Looking to hire for similar positions in Chicago, IL or in other cities? Our IT recruiting agencies and staffing companies can help.
We help companies that are looking to hire Technical Operations Analysts for jobs in Chicago, Illinois and in other cities too. Please contact our IT recruiting agencies and IT staffing companies today! Phone 630-428-0600 ext. 11 or email us at jobs@nextstepsystems.com. Click here to submit your resume for this job and others.
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