We're a growing Managed Services Provider based in the Chicagoland area, and we're looking for a Level 2 Service Desk Technician who's skilled in both macOS and Windows support and has experience working for a MSP. This is a client-facing role for someone who thrives in fast-paced environments, enjoys solving problems, and brings previous MSP experience to the table.
You'll join a collaborative team that values innovation, career development, and work-life balance. After three weeks of in-office training, you'll shift to a mostly remote setup (80% WFH / 20% onsite support in and around Streamwood).
Key Responsibilities:
- Resolve escalated Windows 11 and macOS issues within expected SLAs
- Build and manage macOS deployment workflows using JAMF, FileWave, or similar tools
- Support Apple Business Manager and other MDM platforms
- Troubleshoot desktop, server, VoIP, and remote work setups
- Maintain thorough documentation and accurate ticket records
- Assist with mobile device management, networking issues, and app support
- Participate in certification programs and technical training
What You Bring:
- At least 1 year of experience supporting clients at a Managed Service Provider (MSP)
- Proficiency in troubleshooting both macOS and Windows environments
- Familiarity with MDM tools and Apple Business Manager
- Strong understanding of workstation/server communication and remote support tools
- Basic networking and VoIP knowledge
- Mac administration certifications like ACSP are a plus
- Exposure to scripting languages like PowerShell, Bash, or Python (preferred)
- Great customer service skills and an organized, self-directed work style
Compensation & Benefits:
- 100% employer-paid health, dental, and vision insurance
- Work-from-home 80% of the time after onsite training
- 401(k) with 3% company match
- 13 PTO days + 7 paid holidays
- Mileage reimbursement for Chicagoland client visits
- Ongoing training, cert reimbursement, and career growth support
If you're an MSP-experienced tech who loves tackling escalated issues and wants to grow in a supportive, hybrid environment-let's connect.