Syscon Inc. · 15 hours ago
Local Senior IT Technician (MSP) - WFH + Local Client Visits
Chicago, IL
Full-time
Hybrid
Senior LevelSyscon, Inc. is a growing Managed Services Provider (MSP) supporting small to mid-sized businesses throughout the Chicagoland area. They are seeking a Senior IT Technician who enjoys hands-on technical work, advanced troubleshooting, and taking ownership of client outcomes, while benefiting from a work-from-home model when not at client sites.
ConsultingCRMInformation TechnologySoftware
Responsibilities
Provide senior-level remote and on-site technical support to clients
Troubleshoot complex issues involving Microsoft 365, networking, security, and endpoints
Perform hardware and software installations, upgrades, and proactive maintenance
Document all work clearly and accurately in the ticketing system
Work within ticket queues, SLAs, and prioritization standards
Support project work including cloud migrations, security implementations, and client onboarding
Maintain a professional, client-focused approach in all interactions
Qualification
Required
You currently live within approximately 45 miles of Chicago and can travel to local client sites on the same day, as needed
You have hands-on experience working in a Managed Services Provider (MSP) or outsourced IT environment, supporting multiple clients concurrently
You are comfortable working in a ticket-driven environment with SLAs, documentation standards, and shifting priorities
You are accustomed to owning issues from start to finish, including communication, follow-up, and resolution
You are comfortable working remotely from home when not at client sites and managing your time independently
Microsoft 365 (Exchange Online, OneDrive, SharePoint Online)
Azure AD / Entra ID, Conditional Access, Intune, Autopilot
Virtual environments (RDS, Terminal Servers, Azure Virtual Desktop)
Experience using RMM tools for endpoint management
Security tools such as MFA, EDR/AV, and MDM
Networking fundamentals (DNS, DHCP, VPNs, VLANs, firewall rules)
PowerShell scripting (basic to moderate preferred)
Preferred
Prior MSP experience strongly preferred
Experience supporting multiple clients concurrently in an MSP or outsourced IT environment (strongly preferred)
Benefits
Health/Dental/Vision insurance coverage
Unlimited PTO model based on tenure
Retirement savings plan with employer contribution
Travel reimbursement
Opportunity to deepen technical expertise through supported certifications and continued learning
Company
Syscon Inc.
Construction and IT – That’s all we do! You won’t find another company with as much depth, knowledge, and experience.
Founded in 1986
11-50 employees
Funding
Current Stage
Early StageLeadership Team
Lawrence Wendt
Co-founder
Company data provided by crunchbase