MSP Help Desk Escalation Technician - Level 1

Company Description

a COUPLE of GURUS is an award-winning IT services company dedicated to helping organizations through managed IT services, managed cybersecurity, cloud solutions, and IT consulting. We support businesses, regulated manufacturers, and non-profits by providing solutions tailored to their unique needs. Known for our personal and fun approach, we emphasize clear communication and strong client relationships. We partner with organizations to align technology with their vision and help remove the burden of IT.

Role Summary

The Level 1 MSP Escalation Technician is responsible for providing first-line technical support, triaging incoming tickets, and resolving common technical issues in a timely and professional manner. This role focuses on initial troubleshooting, accurate documentation, end-user communication, and proper escalation of unresolved issues to Level 2 or other appropriate resources.

The technician owns assigned tickets from intake through initial resolution or escalation by gathering relevant information, validating symptoms, applying standard troubleshooting procedures, and maintaining clear updates in the PSA system. Responsibilities include supporting end users with day-to-day technical issues, assisting with remote troubleshooting sessions, coordinating follow-up when needed, and ensuring tickets are properly documented and routed. Success in this role requires strong communication, solid technical fundamentals, and the ability to work efficiently in a fast-paced MSP environment.

Core Customer Service Skills

• Clear, professional communication with end users and client contacts, primarily through ticket updates, chat, email, and scheduled troubleshooting sessions.
• Active listening and the ability to ask effective clarifying questions.
• Calm, professional demeanor when handling urgent issues or frustrated users.
• Ability to set expectations clearly and provide timely status updates.

Ticketing and Workflow Skills

• Owning assigned tickets from intake through initial troubleshooting or escalation.
• Accurate categorization, prioritization, and application of SLAs.
• Following established procedures and using the internal knowledge base to resolve common issues.
• Escalating issues appropriately when further investigation, senior support, or vendor involvement is required.
• Maintaining detailed and accurate ticket notes so that next steps are clear for both internal teams and clients.

Technical Skills

• Basic to intermediate Windows troubleshooting, including account issues, profile problems, application errors, printer issues, and general workstation support.
• Microsoft 365 user support, including password resets, mailbox access issues, OneDrive sync problems, Teams basics, and general account troubleshooting.
• Basic networking troubleshooting, including confirming connectivity, checking DNS-related issues, verifying Wi-Fi access, and identifying whether an issue is local or broader in scope.
• Proficiency with RMM and remote support tools to gather information, assist users, and perform approved remediation steps.
• Familiarity with common business applications and basic troubleshooting of line-of-business software in SMB environments.

Troubleshooting Approach

• Gather relevant information before escalating, including symptoms, screenshots, error messages, scope, and recent changes.
• Verify whether the issue affects a single user, multiple users, or an entire site.
• Follow documented procedures and use available tools to isolate common causes.
• Apply standard remediation steps where appropriate and confirm whether the issue is resolved.
• Escalate unresolved or higher-complexity issues with enough detail for Level 2 to continue efficiently.

Collaboration and Escalation Skills

• Properly understand existing ticket notes and troubleshooting work done from a ticket escalated by Tier 1 Help Desk Resources.
• Write clear, complete ticket notes that accurately describe the issue, troubleshooting performed, results, and next steps.
• Escalate with the right context, including impact, urgency, and what has already been attempted.
• Coordinate with Level 2 technicians, vendors, or internal team members when additional support is needed.
• Communicate updates back to the client even when the issue is being handled by another team.

Professional Habits

• Strong time management while handling a busy ticket queue and responding to follow-ups.
• Willingness to learn from escalations and improve troubleshooting skills over time.
• Consistent adherence to MSP standards, including documentation quality, security awareness, and change control.
• A customer-first mindset with attention to detail and accountability.

Required Qualifications

• Minimum 1 year of help desk or technical support experience.
• Strong written and verbal communication skills to document troubleshooting clearly and coordinate resolution with clients and internal teams.
• Ability to follow technical procedures and accurately record issue details.
• Basic Windows familiarity and general computer troubleshooting skills.
• Basic understanding of TCP/IP networking fundamentals
• In Office position. Flexibility to go onsite as needed in the Minnesota Twin Cities area.

Preferred Experience

• 2 to 3 years of help desk or technical support experience.
• Post-secondary education in technology or a related field preferred.
• MSP experience preferred.
• Experience using a PSA or ticketing system.
• Experience with a remote monitoring and management platform.
• Experience coordinating next steps, recommendations, and basic escalation details for unresolved tickets.
• Experience with remote Windows workstation troubleshooting.

Technologies

• Windows operating systems, both server and desktop.
• Microsoft 365 features, including Exchange Online, OneDrive for Business, SharePoint Online, and Teams.
• HPE Instant On networking portfolio
• Fortinet FortiGate portfolio
• ConnectWise Manage.
• ConnectWise Automate.
• ConnectWise ScreenConnect.
• ConnectWise Backup, formerly SkyKick.
• N-able Passportal.
• Kaseya Datto Backup suite, including BCDR, Endpoint for PC, and SaaS.
• Huntress EDR, ITDR, and SAT.
• Windows Defender.