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

Location : Chicagoland Area ( local candidates only – must live within approximately 45 miles of Chicago)
Work Model : Work from home with occasional same-day local client site visits
Schedule : Full-time | Monday–Friday, 8:00 AM–5:00 PM CST

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!

What You’ll Do

• 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

Technical Experience Required

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

Why Join Syscon

• 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

The Syscon Culture
Syscon is a small, growing MSP where ownership, accountability, and follow-through are expectations, not buzzwords.

We value

• Taking responsibility and seeing issues through to resolution
• Clear, direct communication with clients and teammates
• Strong documentation and attention to detail
• Helping teammates succeed and supporting shared goals
• Continuous learning and improvement

We operate under the EOS framework (Traction by Gino Wickman), which provides clarity around roles, priorities, and accountability. In this role, your decisions and execution directly impact client satisfaction and team success.

Additional Details

• Occasional team meetings held in the Chicago area or Phoenix
• Compensation: Competitive salary, aligned with senior MSP experience

**No phone calls regarding this position

Interested? Submit your application to be considered. Selected candidates may be contacted for next steps.

Syscon, Inc. is an Equal Opportunity Employer (EOE) committed to fostering a diverse and inclusive workplace.