Tier 2 Systems Engineer

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

• 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.”