Remote Tier 2 Help Desk Technician | MSP IT & Security

Harbor IT, LLC; Boston (MA); Remote; USD 65,000 - 90,000; Full time

Job summary

Harbor IT, LLC is seeking a Help Desk Technician II to operate in a remote-first capacity with occasional onsite support in the Greater Boston area. The role requires handling complex tickets end-to-end, mentoring junior technicians, and ensuring HIPAA-compliant security practices across healthcare and life sciences environments.

You will troubleshoot Windows 10/11, manage Entra ID and AD, and coordinate with security tooling (EDR, MFA) while leveraging RMM and PSA platforms to maintain Harbor

Qualifications

• Experience in a Help Desk or Service Delivery role, supporting complex IT environments.
• Familiarity with healthcare or HIPAA-regulated settings is a plus.
• Proactive, methodical problem solving and strong documentation skills.

Responsibilities

• Serve as Tier 2 escalation point for complex hardware, software, and network issues.
• Administer and troubleshoot Microsoft 365 services and Entra ID environments.
• Manage endpoint security, patching, and monitoring to meet security and SLA standards.
• Support onsite deployments and collaborate with infrastructure teams as needed.
• Provide technical mentorship to Help Desk I technicians.

Skills

Microsoft 365

Entra ID

Active Directory

Intune

GPO management

MFA

EDR

HIPAA handling

RMM tooling

ConnectWise Manage

N-able RMM

Windows 10/11

Ticketing

Tools

SentinelOne

N-able

ConnectWise Manage

Job description

Harbor IT, LLC is seeking a Help Desk Technician II to operate in a remote-first capacity with occasional onsite support in the Greater Boston area. The role requires handling complex tickets end-to-end, mentoring junior technicians, and ensuring HIPAA-compliant security practices across healthcare and life sciences environments.

You will troubleshoot Windows 10/11, manage Entra ID and AD, and coordinate with security tooling (EDR, MFA) while leveraging RMM and PSA platforms to maintain Harbor