Service Desk Technician II - Midwest

As a Service Desk Engineer II, you will serve as a key technical resource for our clients and service desk team, independently troubleshooting and resolving a broad range of end-user and service-impacting issues across endpoints, Microsoft 365, applications, and connectivity issues. You will also serve as an escalation point for more complex incidents, providing guidance and support to Level I colleagues. 
Beyond resolving tickets, you will be responsible for identifying root causes, recognizing recurring issues, maintaining accurate documentation, and contributing to continuous improvement efforts that strengthen the overall client experience. 

The ideal candidate is a motivated problem solver, strong communicator, and customer-focused technology professional who enjoys helping people and solving technical challenges. You should be comfortable working in a fast-paced environment, managing multiple priorities, and taking ownership of issues from initial contact through resolution or appropriate escalation.   

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

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

Who You Are:
You are a dependable, client-focused problem solver who takes ownership and approaches technical challenges with a methodical, solutions-oriented mindset. You communicate clearly, manage competing priorities, and know when to collaborate or escalate. You look beyond quick fixes, support the growth of less experienced technicians, and continuously improve your technical skills, documentation, and overall service delivery.

• 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 troubleshooting of 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; escalate architecture or redesign needs to the appropriate engineering resource. 

• 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. 
• A collaborative team environment with opportunities to grow within CompassMSP.