IT Technician (Mid–Senior) – Chicago Western Suburbs / Chicagoland

Syscon•Chicago, IL

9h•Hybrid

About The Position

IT Technician – Mid-Level or Senior Chicago Western Suburbs / Chicagoland | Work From Home with Onsite Client Visits Location: Chicago Western Suburbs / Chicagoland Area (local residency required) Syscon is a Managed Services Provider (MSP) supporting small and mid-sized businesses with reliable, practical IT solutions. We are a cloud-first IT services company, focused on Microsoft 365, security, and simplifying client environments while delivering consistent, high-quality support. We are hiring an IT Technician (Mid-Level or Senior) based in the Chicago Western Suburbs / Chicagoland area. This is a home-based role supporting clients throughout the Chicago Western Suburbs and greater Chicagoland area. Most support is delivered remotely, with onsite visits to client locations as business needs require. Candidates must reside within reasonable driving distance of the Western Suburbs to support onsite responsibilities. Level (Mid-Level or Senior) will be determined based on experience, judgment, and ability to work independently. About the Role Work-from-home, client-facing IT support role Onsite client visits within the Chicago Western Suburbs / Chicagoland area as needed Hands-on onsite work involving simple networks, installs, and troubleshooting Primarily cloud-based environments with minimal on-prem infrastructure

Requirements

Strong Tier 2 experience
Solid Microsoft 365 and endpoint support skills
Ability to resolve most issues independently
Good judgment and willingness to ask clarifying questions
Comfort working in a fast-paced MSP or similar environment
Advanced troubleshooting and decision-making skills
Ability to work independently with minimal oversight
Strong client communication and professional maturity
Experience identifying root causes and preventing repeat issues
MSP experience strongly preferred
Microsoft 365 (Exchange Online, SharePoint, OneDrive, Azure AD / Entra ID, Intune)
Endpoint management and RMM tools
Security fundamentals (MFA, EDR/AV)
Networking basics (DNS, DHCP, VPNs, firewalls)
Light on-prem and hands-on networking experience

Nice To Haves

MSP experience strongly preferred

Responsibilities

Provide remote and onsite technical support with professionalism and sound judgment
Support Microsoft 365 environments (Exchange Online, SharePoint, OneDrive, Azure AD / Entra ID)
Troubleshoot endpoint, security, and networking issues
Perform hardware and software installations, updates, and maintenance
Document work and time clearly to support accurate billing and client trust
Communicate clearly with clients, explaining impact and next steps before acting
Identify opportunities to prevent repeat issues and improve environment stability
Migrating file shares to SharePoint Online
Supporting cloud virtual desktop environments
Azure AD / Entra ID configuration and identity management
Security improvements (MFA, endpoint protection, best practices)
Client onboarding and environment cleanup
Backup and disaster recovery support