L2 Help Desk Technician

Hansen Gress is a fast-growing, Alaska-based Managed Services Provider with deep roots in Juneau and active expansion into Anchorage. We’re ~30 people today, scaling quickly, and investing in the people and systems needed to serve our clients with consistency and excellence. 

We run lean, trust our team, and believe in leadership that works alongside people—not above them. We’re relationship-first, execution-focused, and allergic to bureaucracy. If you want to own your work, improve how things get done, and grow into something bigger, this is the right place. 

The Role 

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. 

Who You Are 

• 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. 

Where You'll Work

• Must be based in Juneau or Anchorage 
• This role is primarily on-site, with regular collaboration alongside Level 1 and Level 3 technicians. 
• Remote work flexibility within Alaska where the role permits. 
• This is NOT a fully remote position. 

What’s In It For You 

• Full-time role. 
• Salary: $60,000–$85,000 a year, depending on experience and certifications. 
• Health insurance (with vision coverage). 
• Retirement plans. 
• Mobile device plan reimbursement. 
• A structured path to Level 2 and beyond, with hands-on mentorship from day one. 
• Work in Alaska, where meaningful work meets stunning nature—with mountains, trails, and ocean right outside your door. 

Why You’ll Want to Work with Us  

Employee satisfaction and growth are important to us! We are committed to helping employees dedicate part of their paid time to personal growth through courses and certifications relevant to their specific interests, research and development, and team-building opportunities. See what else our current employees have to say.   
 
Hansen Gress is committed to equal treatment and opportunities for all employees and job applicants. We are dedicated to building an inclusive and diverse company and have no tolerance for discrimination or harassment. We strive to provide meaningful opportunities for all, particularly those who have been traditionally marginalized in tech fields.