Senior Systems Engineer at MSP

Salary: $120,000 - 150,000 per year Requirements:

• We need 5+ years of experience in Windows and Microsoft 365 environments, including multi-site Active Directory and Entra ID work; MSP or similar multi-client experience is strongly preferred.
• We need the ability to design and troubleshoot networks, including WAN/LAN, switching, routing, firewalls, VPN, DNS, and DHCP.
• We need clear communication skills for working with non-technical clients in person, by phone, and in writing.
• We need proven ownership of complex issues and small-to-mid-sized projects without step-by-step guidance.
• We need willingness to work onsite in the Chicago area and participate in after-hours/on-call coverage.
• We require a valid drivers license and the ability to pass a background check.

• We own complex incidents and problems across Windows Server, Microsoft 365, Azure, networking, and security, identifying root cause and improving stability.
• We design and deploy changes to identity, network, and security systems, including Entra ID and Conditional Access, firewalls and VPN, DNS/DHCP, and endpoint protection.
• We lead client projects such as tenant and server migrations, new-site deployments, firewall swaps, and virtualization or backup upgrades.
• We advise clients and internal stakeholders on practical options, risk, and effort before work begins.
• We work onsite in the Chicago area for scheduled maintenance, projects, and consulting.
• We create and maintain environment documentation, standards, and runbooks so work can be handed off smoothly.
• We mentor other engineers through design reviews and difficult tickets, and involve vendors only when an issue falls outside our stack.
• We share after-hours and on-call coverage for monitoring and incident response.

• Active Directory
• Azure
• Firewall
• LAN
• Microsoft 365
• Network
• Security
• VPN
• Windows
• Office 365
• Cloud
• PowerShell
• SharePoint
• VMware

More:

We are an established managed services provider that designs, implements, and supports secure IT environments for growing businesses and nonprofits. Our focus is on proactive operations and cybersecurity so our clients can concentrate on running their organizations instead of their infrastructure. This is a hands-on, client-facing senior engineering role based in the Chicago 60602 area with hybrid remote work, regular onsite client visits, and a Monday through Friday schedule with rotating after-hours coverage. Compensation typically ranges from $120,000 to $150,000 and includes a competitive base salary, performance bonus opportunities, PTO, 401(k) with match, medical, dental, vision, life, AD&D, short- and long-term disability, employee assistance, professional development, and tuition assistance.

last updated 39 week of 2026