Syscon Inc. · 23 hours ago
IT Technician – Mid-Level or Senior (Chicagoland)
Chicago, IL
Full-time
Hybrid
Mid, Senior LevelSyscon Inc. is a Managed Services Provider supporting small and mid-sized businesses with reliable IT solutions. The IT Technician role involves providing remote and onsite technical support, primarily in Microsoft 365 environments, with occasional client visits for installations and troubleshooting.
Enterprise SoftwareConsultingSoftwareInformation TechnologyCRM
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
Qualification
Required
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
Technical experience with 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
Chicagoland residency required
Preferred
MSP experience strongly preferred
Benefits
Unlimited PTO based on tenure
Medical, dental, and vision insurance
Retirement plan with company participation
Paid holidays
Mileage reimbursement for onsite client visits
Supportive, people-first team environment
Company
Syscon Inc.
Construction and IT – That’s all we do! You won’t find another company with as much depth, knowledge, and experience.
Founded in 1986
11-50 employees
Funding
Current Stage
Early StageLeadership Team
Lawrence Wendt
Co-founder
Company data provided by crunchbase