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Help Desk II at Harbor IT: 100% Remote (Boston, MA)

Title: Help Desk II

Location: Boston, MA

Department: Managed IT

Job Description:

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 to ensure uptime and performance across the client portfolio.
Create and maintain accurate internal and client-facing documentation, including knowledge base articles, network diagrams, asset inventories, and standard operating procedures.
Identify recurring issues, inefficiencies, or improvement opportunities in the client environment and escalate or propose solutions through the Pod Manager and Account Team (CSM and CIO).
Mentor and guide Help Desk I technicians through ticket resolution, knowledge transfer, and professional development feedback.
Participate in emergency on-call rotation, responding to after-hours incidents, outages, and critical client escalations as scheduled.
Engage in team knowledge-sharing, training, and process-improvement initiatives

Qualifications & Skills:

Working experience across the Microsoft 365 and Azure platform (setup, configuration, troubleshooting) including Office, Exchange, Teams, SharePoint/OneDrive, and Entra ID.
Experience with Active Directory administration including GPOs, user/group management, and hybrid identity configurations.
Demonstrated proficiency with ticket triage, prioritization, and root cause analysis in an MSP or professional services environment.
Familiarity with modern endpoint and mail security tooling: EDR/antivirus/mail filtering platforms (e.g., SentinelOne, Microsoft Defender for Endpoint, Proofpoint, Mimecast, Barracuda), MFA and identity platforms (e.g., Duo, Okta, Entra ID).
Conceptual understanding of networking fundamentals: firewalls, switching, DNS/DHCP, and wireless (exposure to Meraki, Fortinet, or Palo Alto a plus).
Basic familiarity with backup and storage technologies (e.g., Veeam, Cove, Datto, cloud backup platforms).
Confidence with basic AI concepts and use cases, with an emphasis on security and data and IP governance.
Comfort working in healthcare-adjacent environments with sensitivity to HIPAA, PHI handling, and clinical/lab operational constraints.
Strong troubleshooting, logic, and critical thinking skills.
Strong written and verbal communication skills, including the ability to translate technical issues into plain language for non-technical clinical and administrative staff.
Self-motivated with strong time management and the ability to manage multiple priorities in a fast-paced, ever-changing environment.
Ability to identify and articulate opportunities for improvement within a client’s environment.
Demonstrated ability to mentor and develop junior technicians.
Focus on continuous professional development in the technology industry and willingness to achieve technical certifications required to support our client and partnership needs.

Education & Experience:

Bachelor’s degree in Information Systems, Computer Science, or related discipline preferred.
3+ years of IT support experience, ideally in a Managed Service Provider or professional services environment.
Experience supporting Microsoft 365, Intune, and MFA.
Certifications such as CompTIA Network+, Microsoft 365 Certified: Modern Desktop Administrator, or equivalent preferred.

Work Environment:

Reports to the Pod Manager within Harbor IT’s service delivery organization.
Fast-paced, collaborative MSP culture with opportunities to expand into project work or system administration.
Remote-first role with occasional onsite client visits; this posture may shift as client and business needs evolve.
Fast-paced, collaborative MSP culture with opportunities to expand into project work, field technician roles, or system administration.
Exposure to enterprise-grade tools and clients across healthcare, medical, and life sciences industries.
Participates in a scheduled emergency on-call rotation covering after-hours incidents.

Benefits: