Head Server Jobs in Alaska (NOW HIRING)

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’rerelationship-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 MSP Technical Lead(L3) is our highest individual-contributor technical role and one of the most important seats in the company. You will operate across our three core technical functions—Help Desk, Projects, and Centralized Services—but will typically be hired into one or two concentrated areas.
In this role, you’ll be the person we trust with our hardest problems, most complex client environments, and most critical escalations. You’re the person who holds the line when things get hard and makes things better when they’re not.
This isn’t just a “senior tech” role. You’re expected to identify patterns across clients, build and improve processes, reduce key-person risk through documentation and training, and proactively raise the technical bar across the team. You bring structure and repeatability to everything you touch.
Successful and consistent performance at this level will position you for future leadership and specialization opportunities, including roles like Onboarding Manager, Help Desk Manager, Centralized Services Manager, and others as the company grows.

Technical Execution

• Take ownership of complex, high-priority escalations from L1 and L2 technicians across Help Desk, Project, and Centralized Services functions.
• Resolve advanced issues involving Windows Server environments, Microsoft 365, Active Directory, Group Policy, DNS, and enterprise security configurations.
• Configure,maintain, and support virtualization platforms including Hyper-V—VM builds, migrations, and ongoing maintenance.
• Administer and troubleshoot Azure Virtual Desktop (AVD) environments and related Microsoft cloud technologies.
• Configure and troubleshoot firewalls, switches, VLANs, VPN connectivity, and LAN/WAN infrastructure across platforms including SonicWall and Ubiquiti.
• Utilize PowerShell and CMD scripting for automation, troubleshooting, and system administration tasks.
• Leverage AI tools actively and fluently to force-multiply your output—whetherthat’saccelerating documentation, automating repetitive work, diagnosing complex issues faster, or building better client-facing materials. At L3, AIproficiencyis a professional expectation, not a nice-to-have.
• Anticipate technical risks before they become client problems—evaluate business impact, flag issues proactively, andmaintainclear records of outcomes and contributions.

Process, Documentation & Knowledge

• Create and improve processes—not just follow them. At L3,you’reexpected to lead documentation standards and build repeatable systems that reduce key-man risk.
• Actively train and teach teammates.You’reresponsible for helping others grow, not just solving problems yourself.
• Build playbooks, standardize delivery, andidentifyopportunities for automation that improve consistency and scale across the team.
• Document client environments, recurring issues, and resolutions so that institutional knowledge lives in the system, not just in your head.

Communication & Client Experience

• Communicate clearly and proactively with clients and internal staff—especially in high-pressure situationswhereconfidence and clarity matter most.
• Set and manage client expectations accurately, keeping relevant stakeholders informed on timelines, risks, and progress.
• Communicate trends, risks, and service improvements upward to leadership with context and clarity.
• Understand your clients’ businesses, not just their technology. L3 technicians are expected to know how a clientoperates, what matters to their leadership, and how a technical issue or recommendation translates intoreal businessimpact.
• Represent Hansen Gress professionally in every client interaction—this role carries real weight in how clients experience us.

Ownership & Accountability

• Own your outcomes—not just your tasks.You’reaccountable for the quality, completeness, and follow-through on everything you touch.
• Prioritize effectively across competing demands. Help Desk volume, project timelines, and centralized service delivery all require judgment about what matters most.
• Proactivelyidentifywhat’snot working—across your own work, team processes, and client environments—and do something about it.
• Mentor junior technicians and invest in their development as a direct expression of your own leadership potential.

• You have substantial IT support experience—typically 5–10+ years—with meaningful time in an MSP or IT services environment. We care more about the depth of whatyou’vebuilt and solved than the number of years on your resume.
• You’veearned the L3 designation through demonstrated capability—not just tenure. Youoperateat this level consistently, not occasionally.
• Youidentifypatterns across tickets and client environments and use them to prevent problems, not just react to them.
• You’rea strong communicator in both directions—clear with clients, and clear with leadership. Youdon’tlet things fall through the cracks silently.
• You take documentation seriously. You understand that knowledge trapped in one person’s head is a liability, and you build systems that outlast any individual.
• You mentor others naturally. Sharing what you knowisn’ta burden—it’spart of how you define doinga good job.
• You’reorganized, detail-oriented, and process-driven—but you can also move fast when the situation calls for it.
• You’readaptable. In an MSP environment, no two days are the same, andyou’reenergized rather than frustrated by that reality.
• You are a recognized subject matter expert across the full Hansen Gress technology stack—not a generalist who knows a little about everything, but someone the team and our clients can point to andsay“ask them.” You hold deep, current, hands-onexpertiseacross the platforms and disciplines we deliver.
• You are technically reliable—the kind of person whodoesn’tspeculateout loud,doesn’tguess under pressure, anddoesn’tputwrong informationinto the world. At L3, the team and our clients defer to you. That trust is earned and protected by a consistent commitment to getting it right.
• 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”onAlaska and fits our team and culture.

• Deep, hands-onexpertisein Microsoft 365/O365 administration—including Exchange Online, Teams, SharePoint, Intune, Entra ID (Azure AD), licensing management, and tenant-level configuration and troubleshooting.
• Hands-on experience managing Hyper-V environments, including VM builds, migrations, and maintenance.
• Strong understanding of LAN/WAN networking with experience configuring and troubleshooting VLANs, managed switches, and connectivity issues across platforms such as Ubiquiti and SonicWall.
• Advanced experience configuring and troubleshooting firewalls, including routing, VPN, access policies, and network segmentation.
• Experience administering Azure Virtual Desktop (AVD) and Microsoft 365 cloud technologies.
• Basic to intermediate scripting and automation experience using PowerShell and CMD.

• 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.

• Must be based in Juneau or Anchorage, Alaska
• This role requires regular face-to-face collaboration in Juneau, Anchorage, and other Alaska communities.
• This isNOTa fully remote position

• Full-time role
• Salary: $100,000–$125,000 a year, depending on experience
• Health insurance (with vision coverage)
• Retirement plans
• Work inJuneauor Anchorage with relocationassistance

Employee satisfaction and growthareimportant 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.
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 toprovide meaningful opportunities for all, particularly those who have been traditionally marginalized in tech fields.