Systems Engineer — Windows & Cloud Infrastructure

North Star Strategies; Chicago (IL); Hybrid; USD 90,000 - 120,000; Full time

Benefits offered by this job

Hybrid role

Job summary

North Star Strategies is seeking a Systems Engineer to join a lean, high-performing IT team that supports corporate infrastructure and executive users in Chicago.

This hands-on role requires professionalism, ownership, and technical depth in a fast-paced environment, with strong collaboration across leadership and technical peers to maintain a secure, scalable IT environment across multiple offices.

Qualifications

• 3+ years of systems administration in an enterprise environment.
• Strong Microsoft 365 administration experience, particularly with Intune/Endpoint Manager.
• Experience supporting both cloud and on-prem Active Directory environments.
• Familiarity with TCP/IP networking, subnetting, MDM, RMM tooling, and PowerShell.
• Working knowledge of virtualized environments.
• Professional troubleshooting and communication skills.
• Ability to prioritize effectively and operate independently in a fast-moving environment.
• Certifications are highly valued.
• Experience in financial services or professional services is a plus.

Responsibilities

• Administering and supporting a Windows-based enterprise environment across office and remote users.
• Managing escalated support issues beyond basic helpdesk troubleshooting.
• Supporting Microsoft 365 services including Exchange Online, SharePoint Online, Teams, and OneDrive.
• Managing identity and endpoint platforms including Microsoft Entra ID and Intune.
• Supporting endpoint deployments, policies, device lifecycle management, and MDM operations.
• Assisting with networking support across Cisco Meraki firewalls, switches, and wireless infrastructure.
• Administering and supporting business-critical SaaS platforms including Egnyte, RingCentral, and Microsoft365.
• Executing approved system changes and operational procedures with attention to detail and documentation.
• Providing recurring onsite support in downtown Chicago.
• Maintaining documentation for systems, workflows, procedures, and operational standards.

Skills

Troubleshooting

Communication

Independence

Executive support

Learning mindset

Teamwork

Tools

Intune

Endpoint Manager

Active Directory

PowerShell

Virtualization

RMM tooling

Cisco Meraki

Egnyte

RingCentral

Microsoft 365

Job description

North Star Strategies is seeking a Systems Engineer to join a lean, high-performing IT team that supports corporate infrastructure and executive users in Chicago.

This hands-on role requires professionalism, ownership, and technical depth in a fast-paced environment, with strong collaboration across leadership and technical peers to maintain a secure, scalable IT environment across multiple offices.