Help Desk II
About The Position
The Help Desk Technician II is a remote-first support role in Harbor IT’s Service Delivery organization and Managed Services practice. The role serves as a primary escalation point for complex support tickets across healthcare, medical, and life sciences clients. It owns tickets from intake and triage through resolution and documentation, while providing technical mentorship to Help Desk I technicians. The position supports varied client environments and helps maintain operational stability and high-quality customer service, with particular attention to uptime, data security, HIPAA and PHI handling, and clinical and laboratory operations. It calls for methodical troubleshooting, critical thinking, professionalism, and an ongoing commitment to professional growth. The role reports to the Pod Manager and is described as a developmental pathway into other Service Delivery career tracks. The position is primarily remote, with occasional onsite client support in the Greater Boston area. It includes a scheduled emergency on-call rotation for after-hours incidents, outages, and critical client escalations. The role works in a fast-paced, collaborative MSP environment, with opportunities to expand into project work, field technician roles, or system administration.
Requirements
- Working experience with Microsoft 365 and Azure setup, configuration, and troubleshooting, including Office, Exchange, Teams, SharePoint/OneDrive, and Entra ID.
- Experience administering Active Directory, including GPOs, user and group management, and hybrid identity configurations.
- Demonstrated proficiency in ticket triage, prioritization, and root cause analysis in an MSP or professional services environment.
- Familiarity with endpoint and mail security tooling, MFA, and identity platforms.
- Conceptual understanding of networking fundamentals, including firewalls, switching, DNS/DHCP, and wireless.
- Basic familiarity with backup and storage technologies.
- Confidence with basic AI concepts and use cases, particularly security and data and intellectual property governance.
- Comfort supporting healthcare-adjacent environments with sensitivity to HIPAA, PHI handling, and clinical and laboratory operational constraints.
- Strong troubleshooting, logic, and critical-thinking skills.
- Strong written and verbal communication skills, including the ability to explain technical issues in plain language to non-technical clinical and administrative staff.
- Self-motivation, strong time management, and the ability to manage multiple priorities in a fast-paced, changing environment.
- Ability to identify and articulate opportunities for improvement in client environments.
- Demonstrated ability to mentor and develop junior technicians.
- Commitment to ongoing professional development and willingness to earn technical certifications required for client and partnership needs.
- At least 3 years of IT support experience; MSP or professional services experience is ideal.
- Experience supporting Microsoft 365, Intune, and MFA.
Nice To Haves
- Bachelor’s degree in Information Systems, Computer Science, or a related discipline.
- Exposure to Meraki, Fortinet, or Palo Alto networking equipment.
- Certifications such as CompTIA Network+, Microsoft 365 Certified: Modern Desktop Administrator, or equivalent.
Responsibilities
- Serve as the Tier 2 escalation point for Help Desk I technicians, resolving advanced hardware, software, and network issues.
- Administer and troubleshoot Microsoft 365 services, Entra ID, Active Directory, and Intune-managed endpoints, including GPO management and security configurations.
- Troubleshoot Windows 10/11 issues, including user profile corruption, printer and network connectivity failures, and MFA-related problems.
- Apply foundational security practices, including MFA and Conditional Access administration, EDR monitoring and response, and HIPAA/PHI handling practices.
- Manage endpoint security and patching through RMM and security tools to meet Harbor IT security and SLA standards.
- Use RMM and PSA tools to manage tickets, patching, monitoring alerts, and asset records in accordance with SLA standards.
- Collaborate with infrastructure and project teams on client deployments, migrations, and server upgrades.
- Perform proactive system monitoring and maintenance to support uptime and performance across client environments.
- Create and maintain internal and client-facing documentation, including knowledge base articles, network diagrams, asset inventories, and standard operating procedures.
- Identify recurring issues, inefficiencies, and improvement opportunities, and escalate or propose solutions through the Pod Manager and Account Team.
- Mentor and guide Help Desk I technicians through ticket resolution, knowledge transfer, and professional development feedback.
- Participate in a scheduled emergency on-call rotation and respond to after-hours incidents, outages, and critical client escalations.
- Participate in team knowledge-sharing, training, and process-improvement initiatives.
Benefits
- Competitive salary commensurate with experience.
- Comprehensive benefits package including health, dental, and vision insurance.
- 401(k) retirement plan with company match.
- Unlimited PTO and holidays.
- Professional development opportunities.
- Company-provided laptop and equipment.
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
No Education Listed
