Level 2 IT Support Technician (Maui Residents Only)

Hawaiian Breeze Solutions; Hawaii; On-site; USD 60,000 - 80,000; Full time

Job summary

Hawaiian Solutions is seeking an experienced Level 2 IT Support Technician based on Maui, with on-site duties and occasional inter-island travel. You will own escalated tickets, perform system fixes, and help create SOPs to improve service quality.

The role requires strong Windows, AD and Microsoft 365 skills, plus IT security awareness. Travel to client sites and participation in an on-call rotation are expected.

Qualifications

• Four or more years of IT support experience.
• Experience resolving escalated issues in an MSP or multi-client environment.
• Experience creating technical documentation and repeatable procedures.
• Willingness to travel to other islands as needed.

Responsibilities

• Take ownership of escalated Level 1 tickets and see them through resolution or formal escalation.
• Troubleshoot issues not covered by SOPs across computers, accounts, and applications.
• Perform system-level fixes and adjust configurations.
• Notify leadership when a broad impact or service disruption is identified.
• Work on advanced monitoring alerts and escalate when necessary.

Skills

Windows OS

Active Directory

Microsoft 365

Networking basics

Troubleshooting

Customer communication

Education

High school diploma

Technical education or equivalent

CompTIA Network+ or similar

Tools

Autotask

IT Glue

Datto RMM

NinjaOne

Job description

Level 2 IT Support Technician (Maui Residents Only)

Hawaiian Solutions

Location: Must live on Maui, Hawaii. On-site at our office, with travel to client sites, occasional inter-island travel and an on-call rotation. Outer island applicants won't be considered.

About the Role

Hawaiian Solutions is looking for an experienced Level 2 IT Support Technician to take ownership of escalated technical issues across multiple client environments. You will resolve tickets that Level 1 cannot close, perform system-level fixes, work advanced monitoring alerts, and help raise the quality of our service by finding root causes and turning repeatable fixes into clear standard operating procedures (SOPs).

This is a hands-on role for someone who owns a problem from start to finish, knows when and how to elevate, and communicates clearly with clients and teammates. You will work closely with Level 1 technicians, Level 3 engineers and our service delivery team, and you will help guide Level 1 technicians as they grow.

Key Responsibilities

Escalated Tickets and System-Level Fixes

• Take ownership of tickets escalated from Level 1 and keep them through resolution or formal escalation. Reassign a ticket only when it is resolved, formally escalated to Level 3, or when service delivery leadership directs it.
• Troubleshoot issues that are not covered by existing SOPs, working across computers, user accounts and applications to complete the work.
• Perform system-level fixes, including restarting services, repairing user profiles, correcting configurations and adjusting system settings.
• Resolve tickets affecting multiple users when the cause and fix are known. Notify service delivery leadership promptly when an issue affects several users or may be a broader service disruption.
• Work advanced automated monitoring alerts that Level 1 could not resolve, and resolve them within scope or **escalate** them appropriately.

Root Cause and Continuous Improvement

• Identify patterns across tickets, alerts and systems, including repeat issues affecting the same users, devices or services.
• Document the suspected root cause or trend, put a permanent fix in place when it is within scope, and elevate when the issue is systemic, unclear or needs higher-level changes.
• Create and improve SOPs so that fixes and implementations can be repeated reliably. Keep instructions clear and usable.

Escalation to Level 3

• Escalate to Level 3 only after reasonable troubleshooting within scope, and when an issue requires system-wide changes, carries risk or is not clearly understood.
• Include complete escalation details: what the issue is, what you tried, what happened, and what you believe the problem or blocker is.

Documentation, Workflow and Communication

• Keep client and internal documentation current as work is completed, including configurations, notes, changes, and root cause and resolution details.
• Follow ticket workflow standards: use the correct ticket status, notes and processes, and do not work outside the ticketing system or skip required steps.
• Give clients clear updates on status, progress and resolution, and never leave a ticket without an update.
• Review assigned tickets for readiness, flag scheduling conflicts, missing information or incorrect ticket data, and notify the service delivery coordinator when work cannot proceed as scheduled.
• When requested, provide technical input to help define project scope by sharing findings, constraints and requirements. Final scope, pricing and solution design are set by others.
• Coordinate with third-party vendors on behalf of clients, including internet service providers, line-of-business software vendors and hardware manufacturers for warranty claims.

On-Call, Location and Travel

• Take part in the team's on-call rotation to provide after-hours support for client issues.
• Work primarily from the Hawaiian Solutions office on Maui, and drive to client sites when a ticket requires on-site work.
• Travel to other Hawaiian islands from time to time as client needs require.

Security and Confidentiality

• Keep all client information strictly confidential, and access client systems only as needed for assigned work.
• Store and handle client credentials and sensitive data securely, using only approved password management and documentation tools.
• Follow least-privilege access practices and report suspected security incidents promptly.

Knowledge, Skills and Abilities

• Working knowledge of Windows, Microsoft 365, user identity, applications, hardware, networking and common business systems.
• Strong troubleshooting skills across multiple systems, services and configurations.
• Ability to independently manage escalated tickets through resolution or proper escalation.
• Ability to diagnose and resolve issues not covered by established SOPs.
• Ability to recognize multi-user, recurring, systemic or higher-risk issues.
• Ability to identify root causes and implement permanent fixes within approved scope.
• Ability to create and improve clear, repeatable SOPs and technical documentation.
• Ability to guide Level 1 technicians and provide constructive technical feedback.
• Strong written and verbal communication skills with both technical and non-technical audiences.
• Ability to evaluate ticket readiness, identify blockers and raise scheduling concerns promptly.
• Commitment to following security, change management and service delivery procedures.
• Strong ownership, judgment, organization and attention to detail.

Technical Experience

• Windows desktop and server environments.
• Active Directory, Microsoft 365 administration and identity management.
• Networking fundamentals, including TCP/IP, DNS and DHCP.
• Routers, switches, firewalls, VPNs and wireless networking.
• Backup and disaster recovery solutions.
• Endpoint protection, multi-factor authentication (MFA) and general IT security practices.
• Troubleshooting systems, services, user profiles and configuration issues.
• Ticketing, remote monitoring and management (RMM), and documentation platforms.

Preferred Tools

• Autotask, our ticketing and service management platform. Experience with Autotask is strongly preferred.
• Other tools we use, where experience is a plus: IT Glue, Datto RMM, SaaS Alerts, Crest, Nerdio, Acronis and NinjaOne.

Preferred Additional Knowledge

• Microsoft Entra ID, Intune, Exchange Online and conditional access policies.
• Virtualization (Hyper-V or VMware) and Microsoft Azure.

Qualifications

• Four or more years of experience in IT support, help desk or systems administration preferred.
• Experience resolving escalated technical issues in a Managed Service Provider (MSP) or multi-client environment.
• Experience creating technical documentation and repeatable procedures.
• CompTIA Network+, a Microsoft Associate-level certification, or a similar industry certification preferred.
• High school diploma or equivalent required; technical education or equivalent practical experience preferred.
• Valid driver's license, reliable transportation, and willingness to take part in the on-call rotation and travel to other islands when needed.
• Ability to pass a background check and drug test.

Physical Requirements

• Lift and carry computer and network equipment weighing up to 50 lbs.
• Work under desks, in server closets and in other tight spaces.
• Climb ladders safely to install or service equipment.
• Sit at a workstation for extended periods while troubleshooting and documenting work.