Tier 2 Systems Engineer (Chicago)

Systems Engineer

Chicago, IL required

North Star Strategies is supporting a highly regarded financial services organization in identifying a Systems Engineer to join a lean, high-performing IT team supporting both corporate infrastructure and executive users.

This is a hands-on role for someone who is comfortable operating in a fast-paced environment where professionalism, ownership, responsiveness, and technical depth all matter. The right person is process-oriented, communicates well with senior stakeholders, and enjoys solving problems across infrastructure, endpoints, SaaS platforms, and user operations.

You will work closely with leadership and technical peers to support day-to-day operations, improve systems, document procedures, and help maintain a stable, secure, and scalable IT environment across multiple offices.

What You’ll Be Doing

• 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

What We’re Looking For

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

The Right Person

We are looking for someone who combines technical capability with accountability and follow-through.

Successful candidates tend to be:

• Process-driven without becoming rigid
• Calm under pressure
• Comfortable supporting executive-level users
• Curious, self-motivated, and continuously learning
• Team-oriented and willing to jump in where needed
• Focused on delivering high-quality user experience and operational reliability
• Someone who says, “If I don’t have the answer, I’ll find the right person who does.”

Additional Details

• Hybrid role based in Chicago
• Approximately one day per week onsite in downtown Chicago
• Full-time opportunity

If you are interested, please apply directly through LinkedIn or contact North Star Strategies for additional information.

North Star Strategies is an equal opportunity recruiting partner. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other protected status under applicable law.