IT Technician – Mid-Level or Senior

Chicagoland | Work 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 ForMid-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).

Syscon Inc.

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IT Technician – Mid-Level or Senior