Help Desk Technician Level 2 (Windows/Mac)

We’re a fast-moving IT service provider supporting businesses throughout the Chicagoland area. As we grow, we’re hiring a Level 2 Technician with real-world MSP experience and a strong background in both macOS and Windows support to help us deliver exceptional service to our clients.

This isn’t a standard help desk job. You’ll be a hands-on technical resource for a wide range of business environments, managing complex support issues, driving resolution, and ensuring smooth operations across endpoint devices, networks, servers, and collaboration tools.

You’ll spend most of your time working remotely—after a short in-office training period, this role shifts to 80% work-from-home with occasional client site visits in the greater Elgin area.

Day to Day Responsibilities:

Taking ownership of escalated technical support issues for macOS and Windows users

Managing macOS environments with tools like JAMF, FileWave, and Apple Business Manager

Troubleshooting VoIP, remote work infrastructure, MDM, and networking issues

Documenting fixes and client environments thoroughly and clearly

Contributing to knowledge-sharing across the service desk team

Staying current on certifications and expanding your technical skill set

Your Background Includes:

1+ year working in an MSP setting, supporting multiple client environments

Proficiency with macOS and Windows 11 systems, including remote support tools

Experience with Apple Business Manager and MDM platforms (JAMF, FileWave, etc.)

Understanding of networking basics (LAN/WAN, DNS, DHCP, VPN)

Exposure to scripting (PowerShell, Bash, or Python) is a bonus

Excellent customer service, documentation, and communication skills

Benefits:

100% company-paid health, dental, and vision insurance

401(k) with 3% company match

80% remote work model after onboarding

13 PTO days + 7 paid holidays

Certification reimbursement + dedicated training resources

Mileage reimbursement for on-site client visits