MSP IT Technician; Mid​/Senior - Remote or Chicagoland

Overview

We are hiring two IT Technicians: one Chicagoland-based and one Remote. Locations:
Chicagoland Area (local candidates required);
Remote (U.S.

-based).

Syscon, Inc. is a Managed Services Provider (MSP) and technology consulting firm passionate about helping businesses thrive through reliable, well-designed IT solutions. We care deeply about our clients and foster a culture where our company, employees, and clients grow and succeed together. 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 , networking, security, and endpoint management.

Level (mid-level or senior) will be determined based on experience and ability to work independently.

• 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

Both roles are hands-on, client-facing positions within a fast-paced MSP environment.

Mid-Level to Senior (based on experience)

• 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
• 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

Senior-Level Candidates Typically Bring
:

• 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
• Power Shell scripting experience (basic to moderate) a plus

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

• 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

Note:

Please no phone calls. Syscon, Inc. is an Equal Opportunity Employer (EOE) committed to fostering a diverse and inclusive workplace.