Systems Engineer (L2/L3 Escalation & Projects)

Job Description

Job Description

Position Summary

This is a full-time, hands-on senior technical role. You own the final internal escalation point for our service desk, execute the Level 2/3 technical work on client infrastructure projects (for example, server and hypervisor replacements, network upgrades, office moves, cloud and Microsoft 365 migrations), and turn client requirements into technical specs the sales team can quote. You'll also lead our security posture work, including reviewing internal and client-facing security policies against the CIS Controls, and carry a few internal improvement projects at a time.

This is not a people-management or a help desk role, as you won't pick up general tickets or coach L1 technicians, own client relationships, or manage project schedules and budgets. Your job is to help with issues escalated to you and make our clients confident their infrastructure is in good hands.

You will be part of the leadership team. This seat is at the table with the owner, the account manager, and the project manager. You'll have a real voice in how we run the company, including which standards we adopt, the tools we buy, how we price work, and where the service desk needs to improve; we expect you to provide feedback and ideas.

In this role, we expect roughly 30% escalation and troubleshooting, 30% project execution (remote prep plus onsite install days), 10% assessments, scoping, and pre-sales engineering, and the balance on security policy alignment, internal tooling, documentation, and the daily huddle. Onsite client work is loosely capped at about 20% of your time.

What We're Looking For

Required:

• 5+ years in an MSP or multi-client IT environment, with at least 2 years as the escalation engineer
• Deep Windows Server, Active Directory, and Hypervisor administration and troubleshooting skills
• Strong Microsoft 365 / Entra ID / Intune skills, including tenant migrations and security baselines
• Solid networking: VLANs, routing, firewalls, site-to-site and client VPN, Wi-Fi design and rollout
• A track record of executing the technical side of infrastructure projects (staging, cutover, technical risks) as part of a team
• Working knowledge of security frameworks and experience mapping policies to technical controls
• Clear written and verbal communication with non-technical business owners; you can explain a risk and a recommendation in plain English, and you're comfortable presenting assessment findings to a prospect
• Comfortable operating as part of a small leadership team, bringing opinions, backing them with data, and taking ownership of the follow-through
• Disciplined documentation and time-logging habits: if it isn't in HaloPSA, it didn't happen
• Valid driver's license and reliable transportation (client sites across Chicagoland)

Nice to Have:

• Azure migration experience (Azure Virtual Desktop in particular)
• Experience with HaloPSA, N-central, Hudu, CIPP, Action1, ConnectSecure, SonicWall, UniFi, or 3CX
• Hands-on experience implementing CIS Controls (IG1/IG2) in an MSP or SMB environment and completing cyber-insurance questionnaires
• Scripting and automation (PowerShell, n8n, or similar)
• Experience with line-of-business applications common to our verticals (ERP, Sage, QuickBooks, document management, etc.)
• Certifications such as MS-102, AZ-104, CCNA, Network+, or Security+
• Experience with AI tools (e.g., ChatGPT, Copilot, Claude) for troubleshooting, scripting, and documentation

Your Responsibilities

• Serve as the final internal escalation point for the service desk; resolve or lead resolution on complex incidents and problems
• Execute the Level 2/3 technical tasks on client infrastructure projects (design, staging, cutover, documentation)
• Perform onsite work when it can't be done remotely, including occasional scheduled evening cutovers
• Perform onsite and infrastructure assessments for new prospects; work with the sales team to turn findings into proposals
• Scope and spec solutions from existing-client requests and site visits; hand the account manager a clear bill of materials and labor estimate
• Review internal and client-facing security policies against the CIS Controls to identify gaps
• Complete client-facing security assessments and cyber-insurance / risk questionnaires alongside the account manager
• Document client environments in our documentation platform; contribute to our build standards
• Own 1-2 internal improvement projects at a time (monitoring, automation, security baselines)
• Participate in the leadership team: weigh in on standards, tooling, pricing, and service desk performance
• Log time accurately in HaloPSA against tickets and projects

Key Duties

• Troubleshoot server, hypervisor, storage, and backup issues across client environments
• Diagnose network performance, VPN, firewall, and Wi-Fi problems; redesign where the root cause is architectural
• Resolve Microsoft 365 mail flow, identity, and device management issues the desk can't close
• Support line-of-business applications (ERP, accounting, document management) at the server and integration layer
• Replace/upgrade Hyper-V hosts, domain controllers, and file servers; decommission legacy systems
• Roll out switching, access points, and firewalls; stand up networks at new client locations and office moves
• Migrate workloads to Microsoft 365, Azure, or AWS, including terminal server to AVD moves
• Conduct onsite infrastructure assessments and network/server mapping for prospects; produce the technical findings and recommendations that feed the proposal
• Conduct technical scoping for existing-client projects and hand the PM and AM a clear scope, BOM, and labor estimate
• Maintain/extend our CIS Controls implementation: review internally deployed controls, map the same controls to client environments, and keep internal and client-facing security policies aligned
• Participate in client security reviews (e.g., NIST CSF interviews with auditors) and complete insurance questionnaires
• Attend the daily huddle and coordinate with the team lead on escalation handoffs

Company Overview

Protek-IT is a managed service provider (MSP) specializing in efficient, personalized IT support for small businesses and non-profits in the Chicagoland area. We support 100+ organizations across 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.

This role exists because our current senior engineer is leaving the industry at year-end. You'll have a structured handover with him before he goes.

• 100% paid Blue Cross Blue Shield healthcare (after 30 days)
• 401(k) with 4% company match (after first year)
• Year-end profit-sharing plan
• Unlimited PTO based on performance and coverage
• Professional development assistance
• Mileage reimbursement for client travel

We're a close-knit team of ten who don't take ourselves too seriously, and we value open, direct communication.

Company Description

We're a close-knit team of ten who don't take ourselves too seriously, and we value open, direct communication.