Senior Systems Engineer; MSP Hybrid​/Work From Home

Senior Systems Engineer (MSP) – Hybrid / Work From Home

Location:
Chicago, IL & Surrounding Suburbs

Work Arrangement:
Hybrid / Local Work From Home

Salary: $100,000–$125,000 annually

Employment Type:
Full-Time | Direct Hire

We are seeking an experienced Senior Systems Engineer (Level
3) to join a growing Managed Service Provider (MSP) in the Chicago area.

This is an excellent opportunity for a hands-on engineer who enjoys solving complex technical challenges, leading infrastructure implementations, and working directly with clients to improve their IT environments.

The ideal candidate has a strong background supporting multiple client environments and is comfortable serving as a senior technical escalation resource while independently executing infrastructure projects.

This is a hands-on engineering position, not a service desk management, project management, or sales role.

The position offers flexibility to work from home, with occasional travel to local client sites for infrastructure projects, assessments, and deployments.

• Serve as a senior escalation resource for complex Level 2 and Level 3 technical issues across multiple MSP client environments.
• Troubleshoot and administer Windows Server, Active Directory, Group Policy, DNS, DHCP, and virtualization platforms.
• Diagnose and resolve server, hypervisor, storage, backup, and disaster recovery issues.
• Design, configure, and troubleshoot network infrastructure, including firewalls, switches, VLANs, VPNs, routing, and wireless networks.
• Administer Microsoft 365, Entra , Intune, Exchange Online, and related cloud services.
• Lead the technical execution of infrastructure upgrades, server migrations, and modernization projects.
• Replace and upgrade Hyper‑V hosts, domain controllers, file servers, and other critical infrastructure.
• Deploy and configure network equipment for new offices, client expansions, and relocation projects.
• Execute cloud migration projects involving Microsoft 365, Azure, AWS, and Azure Virtual Desktop.
• Troubleshoot line-of-business applications, including ERP, accounting, and document management systems.
• Conduct technical assessments of client environments and identify opportunities for infrastructure improvements.
• Participate in client technical reviews, infrastructure planning, and technology roadmap discussions.
• Develop technical scopes of work, bills of materials, and engineering labor estimates for projects.
• Assist with cybersecurity initiatives, including CIS Controls, NIST CSF alignment, security assessments, and compliance requirements.
• Collaborate with project managers, service desk engineers, and technical leadership to ensure successful project delivery.
• Maintain accurate technical documentation, ticket updates, and project records using PSA and documentation platforms.

• 5+ years of IT experience within an MSP or multi-client environment.
• 2+ years of experience handling senior-level technical escalations.
• Strong Windows Server administration, Active Directory, and Group Policy experience.
• Advanced troubleshooting experience with Hyper‑V and/or VMware virtualization environments.
• Strong Microsoft 365 administration, including Exchange Online, Entra , Intune, and tenant migrations.
• Experience implementing Microsoft security policies, conditional access, and endpoint management solutions.
• Strong networking fundamentals involving VLANs, routing, firewalls, VPNs, and wireless infrastructure.
• Experience executing infrastructure projects, including server upgrades, migrations, deployments, and cutovers.
• Familiarity with backup and disaster recovery technologies.
• Ability to independently troubleshoot complex infrastructure issues across multiple client environments.
• Experience…