Service Desk Technician II - Midwest

CompassMSP • ,

13d • Remote

About The Position

As a Service Desk Engineer II, you will serve as a key technical resource for clients and the service desk team. You will independently troubleshoot and resolve a broad range of end-user and service-impacting issues across endpoints, Microsoft 365, applications, and connectivity, and act as an escalation point for complex incidents by guiding and supporting Level I colleagues.

In addition to resolving tickets, you will identify root causes and recurring issues, maintain accurate documentation, and contribute to continuous improvement efforts that strengthen the client experience. The role suits a motivated, customer-focused problem solver who communicates well, manages competing priorities, and takes ownership of issues through resolution or appropriate escalation.

This is a remote position requiring a reliable home office and the ability to work independently while collaborating with a distributed team. On-call availability is required.

Requirements

• 3–5 years in MSP/service desk or comparable support, with demonstrated independent resolution.
• Working knowledge of Windows Server and endpoints, Microsoft 365 administration, Active Directory/Entra ID, MFA, DNS, DHCP, VPN, TCP/IP, and remote access.
• Strong independent troubleshooting, ticket hygiene, and client-facing communication.
• Ability to work independently in a remote role while collaborating with a distributed team.
• On-call availability.
• Dependable, client-focused approach; clear communication; ability to manage competing priorities and take ownership of issues.
• Methodical, solutions-oriented troubleshooting and judgment about when to collaborate or escalate.

Nice To Haves

• MSP or high-volume customer support exposure.
• Familiarity with ConnectWise or similar PSA and RMM tools.
• CompTIA Network+, Security+, Azure Fundamentals, Microsoft role-aligned certifications, or equivalent experience.

Responsibilities

• Independently resolve escalated Windows 10/11, Microsoft 365, Exchange Online, Outlook, Teams, OneDrive, application, printer, VPN, and RDS issues.
• Investigate routine Windows Server service, Active Directory, Entra ID, device enrollment, and network connectivity issues in existing environments.
• Perform authorized account, mailbox, licensing, group, device, and endpoint-management changes.
• Use logs, monitoring, remote tools, and repeatable tests to isolate failures and confirm recovery.
• Support onboarding and offboarding workflows and troubleshoot remote deployment or device configuration.
• Identify common failure patterns and document reusable troubleshooting steps.
• Assist Technician I staff with diagnosis, escalation quality, and technical questions.
• Own assigned client issues or service workflows through completion or an accountable, documented handoff; provide timely updates and clear next steps.
• Maintain complete, accurate records in approved service-management systems, including ticket notes, work performed, client communications, and applicable time entries.
• Follow approved security, identity verification, confidentiality, escalation, and change-management procedures.
• Make authorized changes within established client configurations and escalate architecture or redesign needs to the appropriate engineering resource.

Benefits

• Annual salary plus quarterly bonus opportunities, subject to role and eligibility.
• Progressive, flexible paid time off.
• Medical, dental, vision, life, and disability benefit options.
• Tax-deferred retirement plan with company match, subject to plan terms.
• Career development, technical learning, and coaching opportunities.
• Collaborative team environment with opportunities to grow within CompassMSP.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed