> Markdown version of [/jobs/ext/2144419-l2-help-desk-technician](https://www.wearedevelopers.com/jobs/ext/2144419-l2-help-desk-technician). Every page supports `.md` or `Accept: text/markdown`. Links point to the HTML versions so they work for humans too. Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # L2 Help Desk Technician - **Company:** After School Matters, Inc. - **Location:** Juneau, AK, United States (Remote available) - **Salary:** $60,000.0 - $85,000.0 - **Contract:** Permanent contract - **Skills:** Microsoft Windows, Active Directory, Artificial Intelligence, Computer Networks, Domain Name System (DNS), Windows PowerShell, Azure Active Directory, Microsoft SharePoint, Wide Area Networks, Office365, Microsoft InTune, Information Technology - **Published:** August 20, 2026 - **Apply:** https://msphire.applytojob.com/apply/73KrsskUAL/L2-Help-Desk-Technician?source=GS ## About the Role * You have meaningful IT support experience-typically 2-5 years-including some time in an MSP or IT services environment, or you've clearly outgrown Level 1 work. * You can troubleshoot most day-to-day issues independently and know when to ask for help. * You're starting to see patterns across tickets and clients, and you're curious about the "why," not just the fix. * You communicate clearly with both clients and teammates and keep people informed. * You take documentation seriously and understand that clear notes help everyone, including future you. * You enjoy helping newer technicians and don't mind being asked questions. * You're organized and can manage a mixed workload without things slipping through the cracks. * You're hungry to grow-Level 2 is a stepping stone, and you want to keep building toward Level 3. * Living in Alaska is either a passion of yours or a dream you want to fulfill. We are looking for someone who is "all in" on Alaska and fits our team and culture. Technical Qualifications * Working knowledge of Microsoft 365/O365 administration-Exchange Online, Teams, SharePoint, and basic Intune/Entra ID (Azure AD) tasks. * Solid troubleshooting ability across Windows environments, Active Directory basics, and common connectivity issues. * Working understanding of LAN/WAN networking concepts sufficient to recognize and describe infrastructure issues for escalation, even if you don't configure the fix yourself. * Basic scripting and automation experience using PowerShell and CMD is a plus. What You'll Need * Ability to pass a basic background check for airport security badging * Valid driver's license (or willingness to get one) and the ability to drive. Driver policies apply. ## Description The Level 2 Help Desk Technician independently resolves most ticket types and keeps their queue moving with minimal oversight. You're trusted to manage your own workload, spot patterns across tickets, and keep clients confident even when an issue takes some digging. At Level 2, you're expected to do more than close tickets faster than Level 1-you're building the judgment, technical depth, and communication skills that define a Level 3 Technician, and we actively invest in getting you there. Strong, consistent performance at Level 2 is the clearest path to a Level 3 seat, where you'll take on our hardest escalations and most complex client environments. What You'll Do Technical Execution * Independently resolve most ticket types efficiently and with minimal oversight, including issues involving Active Directory, Group Policy, and DNS at an intermediate level. * Recognize recurring issues and work to reduce them, not just resolve them one ticket at a time. * Prioritize your workload appropriately against overall team demand. * Recognize when an issue is infrastructure-related (network, firewall, server) and escalate it to Centralized Services or Level 3 with clear diagnostic detail. * Use AI tools actively to speed up troubleshooting, documentation, and client communication. * Evaluate basic business impact while troubleshooting, not just technical impact, and escalate at the right time-neither too early nor after a client has already felt the impact. Process, Documentation & Knowledge * Document work consistently and clearly, and look for ways to improve existing documentation. * Create knowledge base articles for recurring issues so the whole team benefits from what you've learned. * Identify process gaps and help close them-your fixes should be repeatable, not one-off. * Begin mentoring Level 1 technicians-answering questions, reviewing their ticket notes, and modeling good troubleshooting habits. Communication & Client Experience * Communicate proactively with clients, teammates, and leadership, maintaining confidence even during more complex issues. * Provide proactive updates to clients throughout troubleshooting, not just at resolution. * Document work so thoroughly that another technician can continue it seamlessly. * Handle difficult conversations professionally when a client is frustrated or a fix is taking longer than expected. Ownership & Accountability * Own your tickets end-to-end and manage your work in the context of what the team needs, not just your own queue. * Actively support teammates during high-volume periods. * Take feedback and turn it into consistent improvement. * Contribute positively to team culture and help set the standard for what good looks like. * Mentor junior technicians and invest in their development as a direct expression of your own growth. ## Related Videos - [Shipping Faster with Less: Render on Cloud Hosting, AI Workloads, and the Future of DevOps](https://www.wearedevelopers.com/videos/1894-shipping-faster-with-less-render-on-cloud-hosting-ai-workloads-and-the-future-of-devops) - [MCP Mashups: How AI Agents are Reviving the Programmable Web](https://www.wearedevelopers.com/videos/1392-mcp-mashups-how-ai-agents-are-reviving-the-programmable-web) - [Autism in Tech](https://www.wearedevelopers.com/videos/427-autism-in-tech) - [Fault Tolerance and Consistency at Scale: Harnessing the Power of Distributed SQL Databases](https://www.wearedevelopers.com/videos/1146-fault-tolerance-and-consistency-at-scale-harnessing-the-power-of-distributed-sql-databases) - [Develop enterprise-ready applications for Microsoft Teams with Azure resources on modern web technologies](https://www.wearedevelopers.com/videos/187-develop-enterprise-ready-applications-for-microsoft-teams-with-azure-resources-on-modern-web-technologies) - [Responsibility Beyond Code - Build with Societal Impact In Mind](https://www.wearedevelopers.com/videos/100041-responsibility-beyond-code-build-with-societal-impact-in-mind) ## Related Articles - [Remote Work: Best Practices for Developers](https://www.wearedevelopers.com/magazine/315-remote-work-best-practices-for-developers) - [Tips on mastering remote job interviews](https://www.wearedevelopers.com/magazine/23-tips-on-mastering-remote-job-interviews) - [How to land a developer job in Amsterdam](https://www.wearedevelopers.com/magazine/36-how-to-land-a-developer-job-in-amsterdam) - [Dev Digest 121 - AI goes offline](https://www.wearedevelopers.com/magazine/456-dev-digest-121-ai-goes-offline) - [The Most Popular IT Jobs on the Market](https://www.wearedevelopers.com/magazine/376-the-most-popular-it-jobs-on-the-market) - [How to Write a CV and Interview if You Don't Fully Qualify For The Job](https://www.wearedevelopers.com/magazine/183-how-to-write-a-cv-and-interview-if-you-don-t-fully-qualify-for-the-job)