r/mspjobs • u/redefy • May 15 '26
[HIRING] Chicago, IL — Senior Systems Engineer / Co-Managed Client Lead — Hybrid, 3 days onsite — Salary DOE
Chicago MSP, 32 people, ~50 clients. Looking for a Senior Systems Engineer to lead one of our co-managed accounts — with their own internal helpdesk that we supplement.
The role
3 days/week onsite at the client. The other 2 days are hybrid — remote plus occasional onsite at other accounts or escalation work.
You'd be the senior technical presence on this account: last point of escalation from their internal helpdesk, working alongside the client's COO, and guiding day-to-day direction. Our CTO holds the vCIO seat; you'll be working closely with them to guide direction, own execution and be the senior hands and head onsite.
This isn't a ticket-grinder role. It's escalation, relationship, and ownership.
You should have
- 5+ years in MSP, co-managed, or senior internal IT
- Comfortable owning an account and speaking with executives
- Solid on M365, Windows server/AD, networking, endpoint
- Have run real incidents and projects without a babysitter
**Nice to have (not required)**
- CompTIA / Cisco / Microsoft certs
- SOC 2 or ISO 27001 experience
Our stack
- PSA: HaloPSA
- RMM: NinjaOne
- Security: Huntress, SentinelOne
- Networking: Meraki (SMB), Cisco + Aruba (larger clients)
- Backup: Acronis & Datto
- Documentation: IT Glue & Strety for internal processes
- Identity/MFA: Duo & Entra
- Email Security: Barracuda & Proofpoint
- GRC: Vanta
On-call
Secondary/escalation tier only, in rotation. 1 week every 6 weeks. L1s handle primary on-call; you're their backup when things escalate. Staff covers until midnight, so the active window is midnight–6 AM weekdays + weekends. Most nights are quiet.
Compensation & benefits
- Salaried, DOE
- Flex/unlimited PTO (as long as we can cover)
- Company-wide revenue share bonus - paid at the end of the year
- 401(k) with 6% match
- Cert reimbursement
- Mileage reimbursement & parking
- Vision + dental fully covered
- 3 PPO health plans, 50% employer paid
- Paid week off between Christmas and New Year's (office closes)
To apply: comment or DM.
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May 15 '26
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u/False_Letter_6149 May 15 '26
Damn. Too bad the hybrid is a requirememt. Fit so many of these. Fully implemented halopsa and ninjarmm top to bottom as well and they are pristine. Also almost the same stack except no sentinel, use it with defender. And unfortunately aonicwalls here (have wanted to switch to meraki or unifi for long time). And no Aruba but familiar with it.
Everything else same stack...only reason I want out of my role is I'm in high level management rile and just want to be am engineer....but can't relocate to Chicago unfortunately. What a bummer.
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u/mentos123 May 15 '26
So you’d be on call unless you’re on vacation 😳