IT Technician (MidSenior) Chicago Western Suburbs / Chicagoland

IT Technician – Mid-Level or SeniorChicago Western Suburbs / Chicagoland | Work From Home with Onsite Client VisitsLocation: 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 RoleWork-from-home, client-facing IT support roleOnsite client visits within the Chicago Western Suburbs / Chicagoland area as neededHands-on onsite work involving simple networks, installs, and troubleshootingPrimarily cloud-based environments with minimal on-prem infrastructureWhat You’ll DoProvide remote and onsite technical support with professionalism and sound judgmentSupport Microsoft 365 environments (Exchange Online, SharePoint, OneDrive, Azure AD / Entra ID)Troubleshoot endpoint, security, and networking issuesPerform hardware and software installations, updates, and maintenanceDocument work and time clearly to support accurate billing and client trustCommunicate clearly with clients, explaining impact and next steps before actingIdentify opportunities to prevent repeat issues and improve environment stabilityProject Work May IncludeMigrating file shares to SharePoint OnlineSupporting cloud virtual desktop environmentsAzure AD / Entra ID configuration and identity managementSecurity improvements (MFA, endpoint protection, best practices)Client onboarding and environment cleanupBackup and disaster recovery supportWhat We’re Looking ForMid-Level Candidates Typically Have:Strong Tier 2 experienceSolid Microsoft 365 and endpoint support skillsAbility to resolve most issues independentlyGood judgment and willingness to ask clarifying questionsComfort working in a fast-paced MSP or similar environmentSenior-Level Candidates Typically Have:Advanced troubleshooting and decision-making skillsAbility to work independently with minimal oversightStrong client communication and professional maturityExperience identifying root causes and preventing repeat issuesMSP experience strongly preferredTechnical ExperienceMicrosoft 365 (Exchange Online, SharePoint, OneDrive, Azure AD / Entra ID, Intune)Endpoint management and RMM toolsSecurity fundamentals (MFA, EDR/AV)Networking basics (DNS, DHCP, VPNs, firewalls)Light on-prem and hands-on networking experienceWhy Join SysconMeaningful work supporting real client environmentsGrowth-focused, collaborative team cultureClear structure and accountability (EOS framework)Opportunity to expand technical depth, ownership, and impactSmall team where your contributions genuinely matterBenefits & PerksCompetitive salary based on experienceUnlimited PTO based on tenureMedical, dental, and vision insuranceRetirement plan with company participationPaid holidaysMileage reimbursement for onsite client visitsSupportive, people-first team environmentRole DetailsFull-timeMonday–Friday, 8:00 AM–5:00 PM (local time)Occasional local travel to client sitesChicago Western Suburbs / Chicagoland residency requiredNote: Please do not call or email regarding this position. All applications must be submitted through the application process.​​​​​​​Syscon is an Equal Opportunity Employer (EOE).