Operating System Engineer Jobs in Glenview, IL (NOW HIRING)

The ideal candidate will have hands-on experience with Windows Server, VMware/Hyper-V virtualization, Active Directory administration, SQL Server backup and restore activities, and a solid understanding of networking fundamentals including switching, routing, firewalls, and IP addressing.

Responsibilities include staging and deploying server, storage, network, and security hardware; loading and configuring Windows Server 2022 environments and applications; supporting data migrations and hardware refreshes; troubleshooting complex issues through log analysis; and working directly with customers throughout implementation and transition. Candidates should be comfortable traveling approximately once per month for onsite migrations and deployments, then providing ongoing remote support until systems are fully transitioned to the customer.

This role supports a large-scale effort to migrate existing VMware-based environments to OpenShift while completing hardware refreshes, software upgrades, and application integrations across customer sites. The engineer will serve as an extension of the field engineering team, staging and rebuilding infrastructure racks, supporting data migrations for primary and disaster recovery environments, and deploying Windows, virtualization, networking, and application components in a standardized architecture. We're looking for hands-on Systems Engineers or Administrators with experience in Windows Server, VMware/Hyper-V, Active Directory, SQL Server, and networking fundamentals who can troubleshoot complex issues and support both onsite migrations and post-deployment activities.

Skills

Windows, VMware Server, Linux, IP Addressing, SQL Server

Additional Skills & Qualifications

• OpenShift or Kubernetes experience (or exposure to containerized environments and platform migrations)
• Windows Server 2022 administration and operating system deployment/image management
• Experience with hardware refreshes, server migrations, and data center deployments
• Familiarity with disaster recovery (DR) environments, backup strategies, and failover testing
• Experience configuring and supporting storage solutions (SAN, NAS, Nimble, Dell EMC, etc.)
• Basic Linux administration and troubleshooting
• Exposure to firmware upgrades, patch management, and infrastructure lifecycle management
• Experience deploying or supporting enterprise applications in customer environments
• Knowledge of public safety, CAD, RMS, or mission-critical systems
• Familiarity with customer-facing implementations, requirements gathering, and technical documentation
• Experience working with structured deployment methodologies or standardized "cookie-cutter" build processes
• Exposure to PowerShell scripting or automation for server administration tasks
• Understanding of load balancers, DNS, DHCP, and network services
• Experience reviewing system, application, and event logs to diagnose complex issues
• Prior experience working in field engineering, professional services, or infrastructure implementation teams
• VMware-to-cloud/container migration experience, particularly involving OpenShift modernization initiatives
• Relevant certifications such as VMware VCP, Microsoft Windows Server, Azure Administrator, CompTIA Network+, CCNA, RHCSA, or OpenShift certifications

Job Type & Location

This is a Contract position based out of Chicago, IL.

The pay range for this position is $50.00 - $60.00/hr.

Eligibility requirements apply to some benefits and may depend on your job classification and length of employment. Benefits are subject to change and may be subject to specific elections, plan, or program terms. If eligible, the benefits available for this temporary role may include the following: • Medical, dental & vision • Critical Illness, Accident, and Hospital • 401(k) Retirement Plan – Pre-tax and Roth post-tax contributions available • Life Insurance (Voluntary Life & AD&D for the employee and dependents) • Short and long-term disability • Health Spending Account (HSA) • Transportation benefits • Employee Assistance Program • Time Off/Leave (PTO, Vacation or Sick Leave)

This is a fully remote position.

This position is anticipated to close on Aug 19, 2026.

We're partners in transformation. We help clients activate ideas and solutions to take advantage of a new world of opportunity. We are a team of 80,000 strong, working with over 6,000 clients, including 80% of the Fortune 500, across North America, Europe and Asia. As an industry leader in Full-Stack Technology Services, Talent Services, and real-world application, we work with progressive leaders to drive change. That's the power of true partnership. TEKsystems is an Allegis Group company.

The company is an equal opportunity employer and will consider all applications without regards to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

We’re a leading provider of business and technology services. We accelerate business transformation for our customers. Our expertise in strategy, design, execution and operations unlocks business value through a range of solutions. We’re a team of 80,000 strong, working with over 6,000 customers, including 80% of the Fortune 500 across North America, Europe and Asia, who partner with us for our scale, full-stack capabilities and speed. We’re strategic thinkers, hands-on collaborators, helping customers capitalize on change and master the momentum of technology. We’re building tomorrow by delivering business outcomes and making positive impacts in our global communities. TEKsystems and TEKsystems Global Services are Allegis Group companies. Learn more at TEKsystems.com.

The company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

San Francisco Fair Chance Ordinance: Pursuant to the San Francisco Fair Chance Ordinance, for all positions located in the city and county of San Francisco, we will consider for employment qualified applicants with arrest and conviction records.

Massachusetts Lie Detector: It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Use of Artificial Intelligence (AI): We may use Artificial Intelligence (AI) to support parts of our hiring process, including sourcing, screening, and evaluating candidates. AI helps assess applications and qualifications, but final decisions are made by our hiring team. By applying, you acknowledge and agree that your application may be reviewed using AI tools.