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 What You’ll Do 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 Project Work May Include 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 What We’re Looking For Mid-Level Candidates Typically Have: 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 Senior-Level Candidates Typically Have: 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 Technical Experience 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 Why Join Syscon Meaningful work supporting real client environments Growth-focused, collaborative team culture Clear structure and accountability (EOS framework) Opportunity to expand technical depth, ownership, and impact Small team where your contributions genuinely matter Benefits
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