[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.