Help Desk II

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

About this position

Harbor IT is a leading Managed Service Provider (MSP) specializing in delivering cutting edge Cybersecurity, IT, and Cloud Services to a diverse portfolio of clients. We pride ourselves on our commitment to excellence, innovation, and customer satisfaction. Harbor IT is backed by investment firm Worklyn Partners since 2022 and has built a national platform through acquisition and rapid organic growth. Our mission is to manage our clients’ technology and mitigate their cyber risks, so that they don’t have to.

Position Overview

The Help Desk Technician II is a remote-first support role within Harbor IT’s Service Delivery organization, serving as a primary escalation point for complex support tickets across healthcare, medical, and life sciences clients. This role owns tickets end-to-end, from intake and triage through resolution and documentation, and provides technical mentorship to Help Desk I technicians. The Help Desk Technician II works across a diverse mix of client environments to maintain operational stability and deliver high-quality service that reflects Harbor IT’s customer service standard. In environments where uptime, data security, and regulatory sensitivity (HIPAA, PHI handling, clinical and lab operations) carry real operational weight, this role demands precision and professionalism. This role requires a growth and development mindset to keep up with the rapidly evolving technology landscape. The Help Desk Technician II approaches troubleshooting with methodical and logical critical thinking. This is a key role in Harbor IT’s Managed Services practice, reporting to the Pod Manager and is a primary developmental pipeline into other Service Delivery career tracks.

Primarily remote with occasional onsite support to clients in the Greater Boston area.

Key Responsibilities

• Serve as the Tier 2 escalation point for Help Desk I technicians, resolving advanced hardware, software, and network issues that exceed first-tier resolution capability.
• Administer and troubleshoot Microsoft 365 (Exchange Online, Teams, SharePoint, OneDrive), Entra ID, Active Directory, and Intune-managed endpoints - including GPO management and security configurations.
• Troubleshoot Windows 10/11 OS issues including user profile corruption, printer and network connectivity failures, and MFA-related problems.
• Apply foundational security practices including MFA/Conditional Access administration, endpoint protection (EDR) monitoring and response, and awareness of HIPAA/PHI handling requirements specific to healthcare and life sciences environments.
• Manage endpoint security and patching through RMM and security tooling (e.g., SentinelOne, N-able) to maintain client environments at Harbor IT’s security and SLA standards.
• Use RMM and PSA tooling (e.g., N-able RMM, ConnectWise Manage) to manage tickets, patching, monitoring alerts, and asset records to Harbor IT SLA standards.
• Collaborate with infrastructure and project teams to assist with client deployments, migrations, and server upgrades.
• Perform proactive system monitoring and maintenance