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Senior Windows Systems Engineer Jobs in Chicago, IL

Parts Town

Senior Cloud Systems Engineer

Addison, IL · Hybrid

$104K - $143K/yr

The Job at a Glance The Senior Systems & Cloud Engineer designs builds, and operate primarily ... Administer, patch, and harden Windows Server and Linux systems across on-prem and cloud ...

Parts Town

Senior Cloud Systems Engineer

Addison, IL · Hybrid

$104K - $143K/yr

The Job at a Glance The Senior Systems & Cloud Engineer designs builds, and operate primarily ... Administer, patch, and harden Windows Server and Linux systems across on-prem and cloud ...

Impact Networking

Systems Engineer

Mettawa, IL · On-site

... of senior engineers; and assist with planning changes and implementing corrective actions. This ... Working knowledge or exposure to Windows Server, VMware/ESXi environments, Active Directory, basic ...

New

Impact Networking

Systems Engineer

Bolingbrook, IL · On-site

... of senior engineers; and assist with planning changes and implementing corrective actions. This ... Working knowledge or exposure to Windows Server, VMware/ESXi environments, Active Directory, basic ...

Impact Networking

Systems Engineer

Hammond, IN · On-site

... of senior engineers; and assist with planning changes and implementing corrective actions. This ... Working knowledge or exposure to Windows Server, VMware/ESXi environments, Active Directory, basic ...

Xerispharma

Senior Systems Engineer

Chicago, IL · On-site

$112 - $140/hr

JR1022** **The Sr. IT Systems Engineer designs, implements, and supports the company's core ... Monitor, maintain, and optimize Windows servers, including routine security patching and ...

New

Impact Networking

Systems Engineer

Chicago, IL · On-site

... of senior engineers; and assist with planning changes and implementing corrective actions. This ... Working knowledge or exposure to Windows Server, VMware/ESXi environments, Active Directory, basic ...

New

Infobahn SoftWorld Inc

Systems Engineer

Elgin, IL · On-site

Windows and Google programs preferable Required Experience Level: Entry Level Work Environment: Office and programming on a showroom floor Key Contributions (First 90-120 Days): Learning system ...

AbbVie

Senior Systems Engineer

North Chicago, IL · On-site

$100K - $137K/yr

As a Sr. Systems Engineer, you will be responsible for the integration of multiple disciplines to ensure robust patient-centric product design and performance. Responsibilities * You will be ...

Prinova Group LLC

Network Systems Engineer

Itasca, IL · On-site

The candidate will work closely with the Senior IT Director - Network Integration and the Network ... Maintain and administer Windows Server, virtualized environments (VMware/Hyper-V), and cloud-based ...

AbbVie

Senior Systems Engineer

North Chicago, IL

$100K - $137K/yr

As a Sr. Systems Engineer, you will be responsible for the integration of multiple disciplines to ensure robust patient-centric product design and performance. Responsibilities * You will be ...

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

Senior Windows Systems Engineer information

See Chicago, IL salary details

$36

$65

$81

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

As of Sep 2, 2026, the average hourly pay for senior windows systems engineer in Chicago, IL is $65.35, according to ZipRecruiter salary data. Most workers in this role earn between $57.45 and $77.98 per hour, depending on experience, location, and employer.

What does a senior Windows systems engineer do?

A Senior Windows Systems Engineer is responsible for designing, implementing, and maintaining complex Windows-based server environments for organizations. They manage system configurations, troubleshoot technical issues, and ensure the security and performance of Windows servers. Additionally, they often lead projects, mentor junior engineers, and collaborate with other IT teams to support business operations. Their role is critical in ensuring that the organization's IT infrastructure runs efficiently and securely.

What are the key skills and qualifications needed to thrive as a senior Windows systems engineer?

To thrive as a Senior Windows Systems Engineer, you need expert knowledge of Windows Server environments, Active Directory, and strong troubleshooting skills, typically backed by a bachelor’s degree in IT or related field. Familiarity with tools like PowerShell, virtualization platforms (VMware/Hyper-V), and certifications such as Microsoft Certified: Windows Server Hybrid Administrator Associate are highly valued. Strong problem-solving abilities, effective communication, and the capacity to work independently or lead teams distinguish top performers in this role. These skills ensure reliable system performance, secure infrastructure, and seamless operations within complex enterprise environments.

What are some common challenges faced by senior Windows systems engineers when managing large-scale enterprise environments?

Senior Windows Systems Engineers often encounter challenges such as ensuring system uptime during maintenance, managing complex Active Directory environments, and troubleshooting issues across multiple Windows servers. Balancing security requirements with user accessibility, keeping up with frequent updates and patches, and coordinating with other IT teams for seamless integration can also be demanding. Effective communication and strong problem-solving skills are key to overcoming these challenges and maintaining a stable, secure infrastructure.

What is the difference between Senior Windows Systems Engineer vs Windows Systems Administrator?

AspectSenior Windows Systems EngineerWindows Systems Administrator
CertificationsMCSE, MCSA, VMwareMCSE, MCSA
Work EnvironmentDesign, implementation, troubleshooting complex systemsDay-to-day maintenance, user support, system monitoring
ResponsibilitiesArchitecting solutions, optimizing performance, leading projectsManaging user accounts, backups, system updates

The Senior Windows Systems Engineer typically focuses on designing and implementing complex Windows infrastructure, while the Windows Systems Administrator handles routine maintenance and support tasks. Both roles require similar certifications and work in Windows-based environments, but the engineer role involves higher-level planning and problem-solving.

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 cities near Chicago, IL are hiring for Senior Windows Systems Engineer jobs?

Cities near Chicago, IL with the most Senior Windows Systems Engineer job openings:

Senior Windows Systems Engineer jobs near you
Infographic showing various Senior Windows Systems Engineer job openings in Chicago, IL as of August 2026, with employment types broken down into 95% Full Time, and 5% Contract. Highlights an 68% In-person, 16% Hybrid, and 16% Remote job distribution, with an average salary of $135,935 per year, or $65.4 per hour.

Senior Endpoint Systems Engineer (HYBRID: Chicago)

Tempus

Chicago, IL • On-site

$130K - $145K/yr

Full-time

Re-posted 25 days ago

Job description

Passionate about precision medicine and advancing the healthcare industry?
Recent advancements in underlying technology have finally made it possible for AI to impact clinical care in a meaningful way. Tempus' proprietary platform connects an entire ecosystem of real-world evidence to deliver real-time, actionable insights to physicians, providing critical information about the right treatments for the right patients, at the right time.
Location: Hybrid: Chicago (3 days on-site)
Position Overview:
We are seeking a highly skilled and strategic Senior Endpoint Systems Engineer to join our IT team. In this role, you will serve as the primary architect and technical lead for the health, security, compliance, and lifecycle management of our global endpoint fleet.
Our environment features a balanced mix of both Windows and macOS devices. We need a senior professional with deep, dual-platform expertise who can design scalable deployment workflows, architect robust endpoint security configurations, and optimize our enterprise toolset-specifically Microsoft Intune, Jamf Pro, and Workspace ONE. As a senior member of the team, you will drive technical strategy, lead complex integration projects, and mentor junior IT staff to ensure a seamless and secure digital employee experience.
Key Responsibilities:
  • Enterprise MDM Architecture: Architect, optimize, and maintain our global Unified Endpoint Management (UEM) infrastructure using Microsoft Intune, Jamf Pro, and VMware Workspace ONE.
  • Strategic Fleet Engineering: Design and scale automated deployment, provisioning, and configuration management workflows for a balanced fleet of Windows 10/11 and macOS hardware.
  • Modern Provisioning & Lifecycle: Standardize and evolve modern deployment frameworks utilizing Windows Autopilot, Apple Business Manager (ABM), and Automated Device Enrollment to achieve zero-touch provisioning.
  • Advanced Scripting & Automation: Develop, test, and maintain robust code repositories (PowerShell for Windows; Bash/Zsh/Python for macOS) to automate complex administrative tasks, custom reporting, and API integrations.
  • Security & Compliance Governance: Partner closely with the Security team to engineer and enforce endpoint security baselines (e.g., CIS Benchmarks), disk encryption protocols (BitLocker, FileVault), and EDR/antivirus agent deployments.
  • Identity & Access Architecture: Lead the integration of endpoint platforms with enterprise identity and access management (IAM) systems (e.g., Entra ID, Okta), including modern single sign-on (SSO) extensions.
  • Tier 3/4 Escalation & Mentorship: Act as the highest tier of technical escalation for complex endpoint, OS, and software issues. Provide mentorship, guidance, and technical training to Tier 1/2 service desk and junior systems administrators.
  • Roadmapping & Documentation: Maintain a forward-looking roadmap for endpoint technologies, evaluate emerging tools, and author authoritative architectural diagrams and standard operating procedures (SOPs).

Required Skills & Qualifications:
  • Experience: 5-8+ years of dedicated experience in endpoint engineering, systems administration, or infrastructure architecture within an enterprise environment.
  • Dual-Platform Mastery: Comprehensive, expert-level knowledge of both Windows and macOS operating systems, system internals, and enterprise deployment methodologies.
  • Enterprise Tooling Expertise: Deep hands-on engineering experience configuring and managing Microsoft Intune, Jamf Pro, and Workspace ONE at scale.
  • Advanced Scripting: Strong proficiency in PowerShell and Bash/Zsh (Python or Swift is a significant plus) for advanced automation, custom scripts, and utilizing MDM APIs.
  • Leadership & Communication: Proven ability to lead projects independently, collaborate across multi-functional engineering teams, and explain complex technical concepts to non-technical stakeholders.

$130,000-$145,000 annually
The expected salary range above is applicable if the role is performed from Illinois and may vary for other locations (California, Colorado, New York). Actual salary may vary based on qualifications and experience. Tempus offers a full range of benefits, which may include incentive compensation, restricted stock units, medical and other benefits depending on the position.
We are an equal opportunity employer. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

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