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).
