Senior Systems Engineer (MSP) - Hybrid / Work From Home (Chicago)

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

About the Opportunity

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.

Key Responsibilities

• 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 ID, 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.

Required Qualifications

• 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 ID, 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 working directly with business owners, executives, and client stakeholders.
• Strong technical documentation, communication, and organizational skills.
• Ability to manage multiple projects and priorities in a fast-paced MSP environment.
• Must reside in the Chicago metropolitan area and be able to travel to client locations as needed.

Preferred Qualifications

• Experience with Azure migrations and Azure Virtual Desktop (AVD).
• Familiarity with AWS infrastructure and cloud migration projects.
• Experience conducting technical discovery, infrastructure assessments, and project scoping.
• Knowledge of CIS Controls, NIST Cybersecurity Framework, and security best practices.
• Experience using HaloPSA or similar MSP ticketing and documentation platforms.
• Previous experience providing technical guidance and mentorship to junior engineers.
• Experience developing client infrastructure roadmaps and participating in technical business reviews.

Compensation & Benefits

Base Salary: $100,000–$125,000 annually , depending on experience.

• 100% company-paid Blue Cross Blue Shield health insurance after 30 days
• 401(k) retirement plan with 4% company match after one year
• Year-end profit-sharing program
• Unlimited PTO based on performance and team coverage
• Professional development assistance
• Mileage reimbursement for client-related travel
• Flexible work-from-home arrangement

Work Location & Schedule

Hybrid / Local Work From Home – Chicago, IL

• Work primarily from home when not required onsite.
• Approximately 20% onsite client travel for infrastructure projects, deployments, and assessments.
• Collaborate remotely with technical leadership, project managers, and service desk teams.
• Must live within reasonable driving distance of Chicago-area client locations.
• This is not a fully remote, nationwide position.

Why Consider This Opportunity?

• Senior Technical Ownership: Take responsibility for challenging escalations, infrastructure projects, and technical decisions.
• Hands-On Engineering: Focus on technical execution rather than managing a service desk or carrying sales responsibilities.
• Diverse Technology Exposure: Work across Microsoft 365, Azure, virtualization, networking, cybersecurity, and cloud infrastructure.
• Client-Facing Impact: Help businesses modernize their environments and make informed technology decisions.
• Work-Life Flexibility: Enjoy a primarily work-from-home schedule with limited onsite client visits.
• Growth Opportunities: Join a collaborative MSP environment where senior engineers contribute directly to technical strategy and infrastructure improvements.