System Administrator Level 2 - Hybrid WFH (MSP)

We are hiring a Level 2 Systems Administrator with MSP experience who thrives in a client-facing environment and enjoys working across Microsoft, security, and infrastructure technologies. This role offers Hybrid WFH flexibility, with a mix of remote support and onsite client visits as needed.

What You Will Do

• Provide day-to-day remote and onsite IT support for end users
• Manage tickets in ConnectWise and ensure clear client communication
• Respond to security, backup, and device alerts
• Support Microsoft 365, Windows Server, SharePoint, and Intune environments
• Assist with deployment projects including upgrades, migrations, and new technology rollouts
• Support VMware ESXi and cloud-based platforms
• Troubleshoot networking issues including TCP/IP and related protocols
• Work with EDR, vulnerability scanning, and security tools
• Collaborate with teammates to improve service delivery and client satisfaction

• 3+ years of IT support experience with exposure to MSP environments
• Strong troubleshooting skills across Windows and Microsoft 365
• Experience supporting networking fundamentals and security tools
• Comfort traveling to client sites as needed
• Professional communication skills and client-first mindset
• Curiosity and enthusiasm for technology

• Onsite training and ongoing career development
• Significant advancement opportunities for outstanding performers
• Health Insurance Plans with employer participation
• Dental & Vision plans
• 401K with employer match participation
• 15 days of PTO for new employees from the start
• Hybrid Work From Home
• Short and Long Term Disability coverage paid for 100% by employer
• Life Insurance coverage paid for 100% by employer
• Company Team Lunches provided every Friday
• Company Outings & Company Parties

Based in Oak Brook, IL, we are a security-focused Managed Service Provider supporting law firms, accounting firms, and investment organizations across Chicagoland. Our team operates with a proactive mindset, helping clients stay ahead of risk through strong standards, modern tooling, and consistent service delivery.