Systems Engineer (Level II) (Chicago)

Level II Systems Engineer

Escalations, Windows Server & Networking | Protek-IT | Chicago, IL (Hybrid) | $80K – $100K

Are you the tech who gets handed the tickets L1 couldn't close, and actually enjoys it? Join Protek-IT as our Level II Systems Engineer: the escalation point for our service desk, remote and onsite, across 100+ client environments. You'll work on Windows Server, Active Directory, Group Policy, Hyper-V, networking, and line-of-business application problems, handle hands-on project work, and be the technical voice when a client needs to understand what's going on.

About the Role

You take escalations from our L1 technicians and resolve them, remotely first and on-site when needed. You also execute Level II technical tasks on client projects (server and hypervisor replacements, network upgrades, office moves), scope new work for our account manager, and join client technical reviews as the technical voice.

This is not a help desk, people-management, or project management role. Our team lead coaches L1, and our dedicated project manager owns project planning, schedules, and budgets. Your job is to execute the technical work, do it right, and flag risks early.

Time split: ~30% escalations and troubleshooting, ~30% project tasks assigned by the PM, ~20% scoping and assessments, ~20% client technical reviews, and the rest on documentation and internal improvements. Onsite client work is about 20% of your time.

What You'll Do

• Own escalated tickets from L1 and drive them to resolution; find the root cause and document the fix so L1 can handle it next time
• Troubleshoot Active Directory, DNS/DHCP, Group Policy, Hyper-V hosts and VMs, and Microsoft 365 mail flow and identity issues
• Diagnose firewall, VPN, switching, VLAN, and Wi-Fi problems; fix configuration and recommend redesign where needed
• Troubleshoot line-of-business applications (e.g., ERP, Sage, QuickBooks, UPS WorldShip, document management etc.) at the server, database, and client level, including upgrades
• Handle vendor escalations and coordination: open and own cases with software vendors, ISPs, carriers, and hardware manufacturers until resolved, keeping the client and team updated
• Execute Level II project tasks (staging, configuration, cutover, documentation) from the PM's plan; occasional scheduled evening cutovers
• Scope client and prospect requests, including site visits, and hand the account manager a clear scope, bill of materials, and labor estimate
• Join the account manager in client technical reviews: environment health, risks, lifecycle replacements, and next steps
• Keep client documentation current in Hudu and log time accurately in HaloPSA

What We're Looking For

Required:

• 3+ years handling Level II escalations in an MSP or multi-client environment, both remote and onsite
• Strong Windows Server administration: Active Directory, DNS/DHCP, Group Policy, file and print
• Hands-on Hyper-V experience: host and VM management, storage, and troubleshooting (Azure a plus)
• Advanced networking: VLANs, routing, firewalls (SonicWall, UniFi, or similar), site-to-site and client VPN, switching, Wi-Fi
• Solid Microsoft 365 / Entra ID administration: mailboxes, mail flow, MFA, conditional access basics
• Experience troubleshooting line-of-business applications and working with vendor support
• Clear communication with non-technical clients, and disciplined documentation and time-logging habits
• Valid driver's license and reliable transportation (client sites across Chicagoland)

Nice to Have:

• Intune/Autopilot, backup and disaster recovery, or PowerShell scripting
• Experience with HaloPSA, N-central, Hudu, CIPP, Action1, ConnectSecure, UniFi, or 3CX
• Scoping work, building BOMs, or joining client technical reviews (TBRs/QBRs)
• Compliance experience: CIS, NIST, HIPAA, PCI, SOC 2, or CMMC readiness, audit support, or cyber-insurance and vendor security questionnaires
• Certifications such as Network+, MS-102, AZ-104, or Security+

Compensation & Benefits

• $80,000 – $100,000 base salary, depending on experience
• 100% paid Blue Cross Blue Shield healthcare (after 30 days)
• 401(k) with 4% company match (after first year)
• Unlimited PTO based on performance and coverage
• Professional development assistance and mileage reimbursement for client travel

Schedule & Location: Monday – Friday, 8 AM – 5 PM. Office at 5019 W Lawrence Ave, Chicago, plus client sites; flexible remote work as results allow.

About Protek-IT

Protek-IT is a managed service provider (MSP) delivering efficient, personalized IT support to 100+ small businesses and non-profits across Chicagoland, including non-profits, labor unions, construction, property management, manufacturing, legal, and professional services. We're a tight team of 10 that goes above and beyond, communicates directly, and has each other's backs.

Interview process: A 30-minute call with the owner, a technical interview with our team, an in-person meeting at our office, and a hands-on troubleshooting session on a real (anonymized) escalation scenario.