IT Technician Mid-Level or Senior (Chicagoland)

IT Technician – Mid-Level or Senior

Chicagoland | W ork From Home with Occasional Onsite Visits
Location : 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 Chicagoland area. This role is primarily work-from-home , with occasional onsite client visits (approximately once per week, on average) . Syscon does not maintain a local office; this is a home-based position.

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
• Occasional onsite client visits within the Chicagoland area
• 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 & Perks

• Competitive salary based on experience
• 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

Role Details

• Full-time
• Monday–Friday, 8:00 AM–5:00 PM (local time)
• Chicagoland residency required
• Occasional local travel to client sites

Note: 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).