Salary: $85,000 - 90,000 per year
Requirements: - We require 5+ years of hands-on IT support experience, ideally in an MSP or other multi-client environment.
- We need someone who can work independently and is comfortable serving as the most senior technical resource on an issue.
- Strong troubleshooting capability across a wide range of technologies is essential, along with sound judgment on when to escalate versus resolve.
- Excellent customer-facing skills are required, including experience managing sensitive or high-profile escalations.
- We need someone who can balance multiple clients, priorities, and projects in a fast-paced setting.
- Strong verbal and written communication skills are required.
- A college degree in IT or computer science is preferred, or equivalent practical experience.
- Windows 11 experience is required; macOS proficiency is preferred.
- Experience with Microsoft 365 / Office applications and O365 admin-level troubleshooting is required.
- Working knowledge of VPN troubleshooting, switches, firewalls, and basic network diagnostics is required.
- Experience with Windows Server and Active Directory / Entra ID administration is required.
- Experience with PSA/ticketing platforms and an RMM tool is required.
- Basic PowerShell scripting ability is a strong plus.
Responsibilities: - We serve as a senior technical escalation point for issues that first-line support cannot resolve across hardware, software, networking, and cloud environments.
- We own tickets from intake through resolution, including triage, prioritization, investigation, implementation of fixes, and client confirmation.
- We work directly with end users and client stakeholders across multiple accounts, adapting to each environment and set of expectations.
- We diagnose and resolve problems involving desktops, servers, networking, and cloud/O365 systems, deciding when a quick fix is sufficient and when a deeper analysis is needed.
- We document all work thoroughly in our PSA/ticketing system, including root cause and resolution steps.
- We identify recurring issues and recommend process, documentation, or infrastructure improvements.
- We mentor Tier 1 support engineers and provide troubleshooting guidance as needed.
Technologies: - Active Directory
- Cloud
- Hardware
- Support
- macOS
- Microsoft 365
- Network
- PowerShell
- Security
- VPN
- Windows
- Office 365
- Android
- Cisco
- Excel
- Hyper-V
- Mobile
- VMware
- Veeam
More:
We are a small MSP seeking an experienced Support Engineer II to join our growing support team in a hybrid remote role based in Rolling Meadows, IL. This position is a senior technical resource for our clients and offers significant autonomy, broad technical exposure, and ownership of issues from start to finish. We invest in engineers who want to expand their skills, and high performers have a clear path toward Senior Engineer, team lead, or specialization tracks in security, cloud infrastructure, or client account ownership. The role offers a salary of $85,000 to $90,000 per year and benefits including 401(k), 401(k) matching, dental, health, life, paid time off, retirement, and vision insurance.
last updated 43 week of 2026