Local Senior IT Technician (MSP) - WFH + Local Client Visits

Syscon • Chicago, IL

26d • Hybrid

About The Position

Syscon, Inc. is a growing Managed Services Provider (MSP) supporting small to mid-sized businesses throughout the Chicagoland area. We’re looking for a Senior IT Technician based in the Chicagoland area 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. This role is ideal for an experienced MSP technician who values autonomy, accountability, and doing quality work the right way.

Before You Apply – This Role Requires This role is not a general IT position. Please apply only if all of the following are true:

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.

If this describes you, we’d love to hear from you!

Requirements

• 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)

Nice To Haves

• Prior MSP experience strongly preferred
• Experience supporting multiple clients concurrently in an MSP or outsourced IT environment (strongly preferred)

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

Benefits

• Work from home when not at client sites
• Competitive compensation
• 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
• Supportive, collaborative team environment
• Real influence over how work gets done and how clients are supported

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed