IT Support Specialist, Tier 2+ (VoIP & MSP):

Please login or register as jobseeker to apply for this job.

: TYPE OF WORK

Full Time

: SALARY

$1,250 to $2,000/M

: HOURS PER WEEK

40

: DATE UPDATED

Feb 18, 2026

JOB OVERVIEW

Who We Are:
We are a fast-growing Hawaii-based IT and VoIP provider supporting small and mid-sized businesses across multiple industries.

We are growing and looking for a technically strong Tier 2 IT Support Specialist who can troubleshoot independently and communicate clearly with business clients.

This is not an entry-level help desk position.

Role Overview:

You will support clients in Microsoft 365, Google Workspace, networking, cybersecurity, and VoIP systems. This role involves direct client interaction, remote troubleshooting, and working across cloud, desktop, and network environments.

We are looking for someone who can think critically, troubleshoot independently, and communicate clearly.

Required Soft Skills
• Strong written and spoken professional English
• Comfortable speaking directly with business owners and end users
• Self-starter who takes ownership of issues
• Calm under pressure
• Able to manage multiple tickets and priorities
• Available to work Hawaii business hours

Core Responsibilities
• Support and administer Microsoft 365 & Google Workspace
• Troubleshoot login, authentication, and access issues
• Configure and support VPN solutions
• Diagnose and resolve network connectivity problems
• Support Windows (10/11) and macOS environments
• Troubleshoot printers, scanners, and peripherals
• Monitor and maintain backup systems
• Support VoIP systems (FreePBX, Grandstream)
• Assist with server administration and Active Directory
• Maintain documentation and ticket notes
• Deliver dependable, professional client communication

Required Technical Experience
Candidate will possess most or all of these skills:

MSP Environment Experience (2+ years preferred)
• Remote troubleshooting
• Ticket-based support workflows
• Client-facing support

Microsoft & Collaboration
• Microsoft 365 Global Admin
• Exchange Online
• SharePoint / OneDrive
• Teams
• Google Workspace Admin

Networking
• TCP/IP fundamentals
• DNS & DHCP troubleshooting
• Firewall basics
• UniFi management experience preferred

Security & Endpoint Management
• Endpoint protection platforms (e.g., ThreatDown, Malwarebytes, etc.)
• RMM tools (Datto RMM preferred)
• Patch management systems

Backup & Recovery
• Synology NAS
• Datto or similar BDR platforms

***

Additional Skills to Be Considered:

VoIP & Telecom (Strong Plus)
• FreePBX
• Grandstream systems
• SIP troubleshooting
• Basic firewall SIP awareness

Cloud & Infrastructure (Nice to Have)
• Microsoft Azure
• AWS
• Rackspace
• Linux administration

Security & Compliance (Nice to Have)
• Cybersecurity best practices
• Microsoft 365 compliance
• HIPAA / SOC 2 familiarity

What Success Looks Like
• Tickets resolved efficiently and documented clearly
• Clients feel confident and supported
• Proactive issue identification
• Minimal escalations
• Strong ownership of assigned accounts

Candidates without MSP experience will not be considered.

To apply, please include:
1. A short paragraph explaining your MSP experience.
2. A description of how you would troubleshoot a Microsoft 365 login issue affecting one user.
3. Your current internet speed (upload/download).
4. Your computer specifications.
5. Confirmation that you can work Hawaii business hours.

SKILL REQUIREMENT

IT Windows Administrator Network Security

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Job Post	Reporter	Rank	Reason	Date

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IT Support Specialist, Tier 2+ (VoIP & MSP):

Please login or register as jobseeker to apply for this job.

TYPE OF WORK

SALARY

HOURS PER WEEK

DATE UPDATED

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