System Engineer L2.5
1 day ago
System Engineer (Level 2.5) – Hybrid | Chicagoland-Based MSP
Location:
Chicago, IL|
Schedule:
Hybrid (2–3 days onsite/week)
Salary:
Competitive ($80K–$95K) + Benefits + Bonus + Fast-Track to Senior Engineering
Are you stuck in a role where you've outgrown the tickets but haven't been given the reins? Ready to take on complex environments, manage deployments end-to-end, and step into senior-level responsibilities with support and mentorship behind you?
We're a fast-moving MSP in the heart of Chicago looking for a sharp, well-rounded
System Engineer (Tier 2.5)
who's ready to dive deeper — someone who's not just familiar with projects and escalations, but thrives in client-facing environments, works autonomously, and wants to carve a real career path in infrastructure, cloud, or leadership.
This is the role for someone who's "almost there" technically and looking for a team that will give you room to grow.
What You'll Be Doing:
- Project Ownership:
Deploy servers, configure and manage firewalls, run migrations (M365, Intune, AD, etc.), and lead small-to-medium client infrastructure projects from kickoff to close - Advanced Support & Escalations:
Be the escalation point for Tier 1s/2s — solving the tough issues they can't, owning tickets end-to-end - Cloud & Hybrid Infrastructure:
Manage Azure AD, Exchange Online, Intune, and Office 365 environments across a variety of SMB clients - Security & Network Config:
Build VLANs, manage SonicWall/Meraki/Ubiquiti environments, implement VPNs, and ensure endpoint protection - Mentorship & Process:
Help shape SOPs and best practices — mentor junior staff and help improve delivery standards - Client Relationships:
Be a trusted face with our clients — present solutions clearly, own issues, and provide guidance that builds trust
Tech You'll Touch:
- Windows Server 2016–2022, Active Directory, GPO
- Azure AD, Intune, Exchange Online, M365
- SonicWall, Meraki, Unifi, VLANs, VPNs
- VMware & Hyper-V & Azure VMs (installations, migrations, management)
- RMM/PSA: ConnectWise, N-Able, Datto, or similar
- Backup & DR: Datto, Veeam, Acronis, etc.
- Cyber Security
Why You'll Love It Here:
- Career Track to Senior Engineer or vCIO
— we promote from within and tailor growth plans - True Project Exposure
— not just maintenance; real-world deployments weekly - Client Variety = Constant Learning
— industries include law, healthcare, finance, creative, and more - Mentorship Culture
— learn directly from experienced Tier 3s and senior architects - Flexible Hybrid Setup
— be onsite for big impact, remote for deep focus - Autonomy + Support
— own your work, but never alone
You Might Be a Fit If You:
- Have 2–6 years of MSP
- Have
project experience
with servers, firewalls, cloud migrations, and networking - Are confident working directly with clients, managing expectations, and communicating clearly
- Can juggle priorities, keep documentation sharp, and act as a technical lead when needed
- Thrive in dynamic, high-accountability environments with room to grow
Compensation & Perks:
- $80K–$95K base depending on experience
- Health, Dental, Vision Insurance
- 401(k) with company match
- PTO + Paid Holidays
- Professional development/certification reimbursement
- Tight-knit, high-skill team culture where people actually support each other
Must have MSP Experience
-
Systems Engineer
5 days ago
Chicago, Illinois, United States Barrow Wise Consulting Full time $120,000 - $180,000 per yearEnjoy problem-solving, need a venue to display your creativity, and emerging technologies peak your interest; if so, Barrow Wise Consulting, LLC is for you. As a multi-disciplined leader, you understand the gifts that set you apart from everyone else. Demonstrate innovative solutions to our clients. Join Barrow Wise Consulting, LLC today.Responsibilities:The...
-
Systems Engineer
6 days ago
Chicago, Illinois, United States Spiderrock Holdings Llc Full time $120,000 - $200,000 per yearSystems Engineer (Mid-Level) will work SpiderRock's established engineers and leadership to help build and scale the core infrastructure that powers our trading platform. This role will take tough systems problems, write high-performance code, and understand how software meets hardware. The mid-level Systems Engineer will work on everything from messaging...
-
Systems Engineer III
3 days ago
Chicago, Illinois, United States Greenfix Property Care Full time $120,000 - $180,000 per yearHourly Pay Range:$ $ The hourly pay rate offered is determined by a candidate's expertise and years of experience, among other factors.Position Highlights:Position: Systems Engineer III - Foundation/Platform TeamLocation: 4901 Searle Parkway, Skokie ILFull TimeHours: Monday-Friday, 8:00am - 5:00pmHybrid PositionJob Summary:The Systems Engineer III is...
-
Manufacturing Systems Engineer
3 days ago
Chicago, Illinois, United States Daniels Health Full time $90,119 - $110,109 per yearOur story began with a passionate idea that we could change the world.... And to be honest, we've never stopped believing that... In 1986 it was a simple concept that microbiology teamed with innovation and clinical contribution could eliminate an issue that was profoundly impacting the healthcare industry – HIV acquired through needle-stick injuries. In...
-
Senior Systems Engineer
6 days ago
Chicago, Illinois, United States The Fountain Group Full time $120,000 - $180,000 per yearThe Combination and Medical Device Products team is developing a replacement infusion system for Parkinson's Disease therapy. We are in the design transfer and launch preparation phase of the project and are looking for high-performing and experienced Systems Engineer to support design improvement projects: design change impact assessments, requirement...
-
Chicago, Illinois, United States Residential Developers Full time $600,000 - $2,400,000 per yearJob SummaryFounding President & Chief Systems EngineerRLD Sustain Engineering and Automation CompanyAbout RLD SustainRLD Sustain Holdings Corporation is building a new, vertically integrated American engineering and development enterprise focused on designing, manufacturing, and operating advanced building systems, energy systems, transportation systems, and...
-
Senior System Engineer
4 days ago
Chicago, Illinois, United States Chicago Financial Search Full time $150,000 - $175,000 per yearJob SummaryCandidate will work with Firm's established engineers and leadership to help build and scale the core infrastructure that powers our trading platform. This role will take tough systems problems, write high-performance code, and understand how software meets hardware. The mid-level Systems Engineer will work on everything from messaging systems to...
-
Sr Systems Engineer
2 days ago
Chicago, Illinois, United States Metra Full time $100,000 - $150,000 per yearJob DescriptionThe final salary will depend on the candidate's qualifications. Those with 8 years or more of required experience can expect offers up to the midpoint of the salary range. Metra provides full pay ranges so candidates can consider their growth potential.Click here to learn more about our benefitsQualified veterans who meet the minimum...
-
Senior Systems Engineer
4 days ago
Chicago, Illinois, United States Apex Fintech Solutions Full time $108,800 - $136,000WHO WE AREApex Fintech Solutions (AFS) powers innovation and the future of digital wealth management by processing millions of transactions daily, to simplify, automate, and facilitate access to financial markets for all. Our robust suite of fintech solutions enables us to support clients such as Stash, Betterment, SoFi, and Webull, and more than 20 million...
-
Systems Engineer II
5 days ago
Chicago, Illinois, United States Motorola Solutions Full time $80,000 - $140,000 per yearCompany OverviewAt Motorola Solutions, we believe that everything starts with our people. We're a global close-knit community, united by the relentless pursuit to help keep people safer everywhere. Our critical communications, video security and command center technologies support public safety agencies and enterprises alike, enabling the coordination...
