Systems Engineer II - Microsoft & Networking

Fairway IT Solutions is seeking a Systems Engineer II - Microsoft & Networking to own network infrastructure and Microsoft 365 administration across our client base. This is a dual-facing role: you will serve as an escalation resource within our Service Center, resolving the technical issues junior technicians can’t close, and you will also be staffed onto client projects alongside our PMO team, executing network builds, M365 migrations, and infrastructure rollouts under a project plan. The ideal candidate is equally comfortable in both modes - reactive incident escalation and planned project delivery - and can context-switch across client environments without losing precision.

Microsoft 365

• Troubleshoot advanced Conditional Access policies, Intune compliance/configuration profiles, and Autopilot deployment at scale - not just applying pre-built policy templates.
• Manage hybrid identity: Entra ID / Entra Connect Sync, on-prem AD to Entra ID synchronization, and federation/SSO troubleshooting.
• Troubleshoot Exchange Online mail flow, transport rules, and connector issues.
• Perform Intune app deployment, PowerShell/Microsoft Graph scripting for bulk administration and reporting, and Defender for Endpoint advanced hunting/incident investigation.
• Participate on M365 tenant-to-tenant migrations and complex Entra ID/Intune deployments as part of client project work.
• Configure and troubleshoot M365 network dependencies - authentication, device compliance, and endpoint security policy enforcement.
• Support backup, DR testing, and recovery documentation for Microsoft 365 and on-prem systems.

Network Engineering

• Maintain LAN/WAN infrastructure across multiple client environments.
• Manage firewalls, switches, and wireless access points (Meraki, Fortinet, Cisco).
• Maintain SD-WAN solutions and ISP redundancy/multi-WAN failover configurations.
• Apply routing protocols (BGP, OSPF), VLANs, QoS, and VPN technologies (IPSec, SSL, SASE).
• Enforce network security policies aligned with client compliance requirements (NIST, CIS).
• Create and maintain network diagrams and configuration documentation.

Service Center Escalation

• Serve as a Tier 2/3 escalation resource for network and Microsoft 365 incidents that junior technicians cannot resolve.
• Troubleshoot escalated incidents and drive resolution with minimal client downtime.
• Monitor and analyze network and system performance; respond to alerts proactively.
• Act as a technical resource for client onboarding and infrastructure assessments.

Project Work

• Execute assigned technical work on client projects - network builds, M365 migrations, security rollouts - following project plans owned by the PMO team.
• Log project hours accurately and communicate technical status to the assigned project lead.
• Flag scope or technical risk on project work to the project lead before it affects timeline or budget.
• Manage multiple concurrent client projects and escalation tickets independently and as part of a team.

• 3+ years of hands-on network engineering experience in a professional IT environment.
• 3+ years of MSP or IT consulting experience strongly preferred.
• Proficiency with Cisco Meraki (MX, MS, MR) and/or Fortinet FortiGate.
• Solid understanding of routing protocols (BGP, OSPF), VLANs, QoS, and VPN technologies (IPSec, SSL, SASE).
• Level II working knowledge of Microsoft 365 administration - hybrid identity (Entra Connect), advanced Conditional Access and Intune compliance/configuration design, Exchange Online mail flow troubleshooting, PowerShell/Graph API scripting, and Defender for Endpoint investigation. This is not a basic user/license administration role.
• Experience with SD-WAN platforms and multi-WAN failover configurations.
• Comfortable operating in both an escalation/support capacity and a structured project environment.
• Strong documentation habits and communication skills (client-facing required).
• Valid driver’s license and ability to travel to client sites within the greater Chicago area.

Certifications (Preferred)

• CCNA or CCNP (Cisco)
• Meraki CMNO (Cisco Meraki Network Operator)
• Fortinet NSE 4 or higher
• Microsoft Certified: Modern Desktop Administrator Associate, Security Administrator Associate, or similar M365-track certification
• CompTIA Network+ or Security+, * Computer networking: 5 years (Required)
• IT Consultant / MSP: 5 years (Required)
• Tier 2/3 Microsoft Systems & Infrastructure configuration: 5 years (Required)

License/Certification:

• CCNA (Preferred)

Referral program, Professional development assistance, 401(k), Health insurance, Retirement plan, 401(k) matching, Paid time off, Vision insurance Full-time, * 401(k)

• 401(k) matching
• Dental insurance
• Employee assistance program
• Flexible schedule
• Health insurance
• Life insurance
• Paid time off
• Professional development assistance
• Referral program
• Retirement plan
• Vision insurance

Fairway IT Solutions is a Chicago-based Managed Service Provider delivering enterprise-grade IT infrastructure, cybersecurity, AI, cloud services, and IT Compliance to small & mid-market businesses across the Midwest. We are professional, client-centric, and committed to building a team where great work is recognized and rewarded.

Our work environment includes:

• Modern office setting with collaborative team culture
• Hybrid schedule with work-from-home flexibility
• Clear advancement path and professional development support