About this position
We are hiring two positions: one Chicagoland-based and one Remote
Locations:
As we continue to grow, we are hiring two IT Technicians - one local to the Chicagoland area and one remote to provide hands-on IT support in a managed services (MSP) environment, supporting Microsoft 365, Azure AD / Entra ID, networking, security, and endpoint management. Level (mid-level or senior) will be determined based on experience and ability to work independently.
About the Roles
Experience level: Mid-Level to Senior (based on experience)
Why Join Syscon
Mid-Level Candidates Typically Bring:
Locations:
- Chicagoland Area (local candidates required)
- Remote (U.S.-based)
As we continue to grow, we are hiring two IT Technicians - one local to the Chicagoland area and one remote to provide hands-on IT support in a managed services (MSP) environment, supporting Microsoft 365, Azure AD / Entra ID, networking, security, and endpoint management. Level (mid-level or senior) will be determined based on experience and ability to work independently.
About the Roles
- Chicagoland-based role: Primarily work-from-home, with occasional same-day onsite client visits (roughly once per week, on average). Syscon does not maintain a local office; this role is home-based.
- Remote role: Fully remote, supporting clients primarily through remote tools
Experience level: Mid-Level to Senior (based on experience)
Why Join Syscon
- Meaningful work supporting real client environments
- Growth-focused, collaborative culture with a strong team mindset
- Clear structure and accountability (EOS framework)
- Opportunity to expand technical depth, ownership, and impact
- Small team where your input genuinely matters
- Provide remote and on-site technical support with professionalism and precision
- Troubleshoot issues across Microsoft 365, networking, security, and endpoint environments
- Perform hardware and software installations, updates, and proactive maintenance
- Document all client issues and time thoroughly to maintain an accurate audit trail
- Ensure work aligns with Syscon’s best practices and quality standards
- Build trusted client relationships through clear communication and follow-through
- Migrating clients to cloud virtual desktop environments
- Moving file shares to SharePoint Online Document Libraries
- Transitioning from Active Directory to Azure AD / Entra ID
- Implementing security features and best practices
- Supporting client onboarding and integrations
- Backup and disaster recovery implementation and testing
- Standardizing and automating recurring tasks and configurations
- For Chicagoland-based technicians, onsite work may include light on-prem networking and hands-on support in generally simple client environments.
Mid-Level Candidates Typically Bring:
- Solid hands-on experience supporting Microsoft 365 environments
- Ability to resolve most user issues independently and escalate appropriately
- Comfort working in a fast-paced MSP or similar environment
- Willingness to learn, accept feedback, and grow technical depth
- Advanced troubleshooting skills and strong technical judgment
- Experience implementing proactive solutions to prevent recurring issues
- Ability to work independently and take ownership of complex environments
- Prior MSP experience strongly preferred
- PowerShell scripting experience (basic to moderate) a plus
- Microsoft 365 (Exchange Online, OneDrive, SharePoint Online, Azure AD / Entra ID, Intune, Autopilot)
- Virtual environments (Terminal Servers, RDS Farms, Azure Virtual Desktop)
- RMM tools and endpoint management
- Security tools such as MFA, EDR/AV, or MDM
- Networking fundamentals (DNS, DHCP, VPN, VLANs, firewall rules)
Benefits & Perks
Syscon, Inc. is an Equal Opportunity Employer (EOE) committed to fostering a diverse and inclusive workplace.
- Competitive salary based on experience
- Medical, dental, and vision insurance
- Unlimited PTO based on tenure
- Paid holidays
- Retirement plan with company participation
- Travel reimbursement for Chicagoland-based role
- Opportunity to grow your skills and career in a supportive, people-first environment
- Full-time positions
- Typical schedule: Monday–Friday, 8:00 AM–5:00 PM (local time)
- Chicagoland role includes same-day local travel as needed
- Periodic team meetings held in Phoenix or the Chicago area
Syscon, Inc. is an Equal Opportunity Employer (EOE) committed to fostering a diverse and inclusive workplace.
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