IT Technician – Mid-Level or Senior

IT Technician – Mid-Level or Senior

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.

• 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

• Provide remote and onsite technical support with professionalism and sound judgment
• Support Microsoft 365 environments (Exchange Online, SharePoint, One Drive, Azure AD / Entra )
• 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  and identity management
• Security improvements (MFA, endpoint protection, best practices)
• Client onboarding and environment cleanup
• Backup and disaster recovery support

• 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
• MSP experience strongly preferred

• Microsoft 365 (Exchange Online, SharePoint, One Drive, Azure AD / Entra , 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

• 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

• 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

• 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).