Help Desk II

Harbor IT is expanding its remote-first support team with a Tier 2 Help Desk role focused on complex, high-priority customer tickets across healthcare, medical, and life sciences organizations. In this position, you will handle escalations end to end, support clients by resolving advanced hardware, software, and network issues, and help grow the team by mentoring Help Desk I technicians.

This hybrid role is based in Boston, MA, with occasional onsite support in the Greater Boston area, as needed for critical client situations and deployments.

What you will do

• Act as the Tier 2 escalation point for Help Desk I, resolving advanced hardware, software, and network issues that require deeper troubleshooting.
• Administer and troubleshoot Microsoft 365 services including Exchange Online, Teams, SharePoint, and OneDrive, along with Entra ID and Active Directory.
• Support Intune-managed endpoints, including GPO management and security configuration work.
• Troubleshoot Windows 10/11 issues such as user profile corruption, printer and network connectivity failures, and MFA-related problems.
• Apply security practices including MFA and Conditional Access administration, and participate in endpoint protection monitoring and response using EDR tooling.
• Maintain HIPAA/PHI awareness and handle information with the sensitivity required in healthcare and life sciences environments.
• Manage endpoint security and patching using RMM and security tools (including examples such as SentinelOne and N-able), aligning with Harbor IT security expectations and SLA standards.
• Use RMM and PSA tools (examples include N-able RMM and ConnectWise Manage) to manage tickets, patching, monitoring alerts, and asset records per SLA requirements.
• Collaborate with infrastructure and project teams to support client deployments, migrations, and server upgrades.
• Perform proactive monitoring and maintenance to support uptime and performance across the client portfolio.
• Create and maintain documentation such as knowledge base articles, network diagrams, asset inventories, and standard operating procedures.
• Track recurring issues and recommend improvements through the Pod Manager and Account Team (CSM and CIO).
• Mentor Help Desk I technicians through ticket resolution, knowledge transfer, and feedback focused on professional development.
• Participate in an emergency on-call rotation for after-hours incidents, outages, and critical escalations.
• Contribute to team knowledge-sharing, training, and ongoing process-improvement initiatives.

What you bring

• 3+ years of working experience.
• Working experience across the Microsoft 365 and Azure platform, including setup, configuration, and troubleshooting for Office, Exchange, Teams, SharePoint/OneDrive, and Entra ID.
• Experience with Active Directory administration, including GPOs, user/group management, and hybrid identity configurations.
• Proven ability with ticket triage, prioritization, and root cause analysis in an MSP or professional services environment.
• Familiarity with endpoint and mail security tooling, including examples: SentinelOne, Microsoft Defender for Endpoint, Proofpoint, Mimecast, and Barracuda; and identity/MFA platforms such as Duo, Okta, and Entra ID.
• Conceptual networking fundamentals including firewalls, switching, DNS/DHCP, and wireless. Exposure to Meraki, Fortinet, or Palo Alto is a plus.
• Basic familiarity with backup and storage technologies (examples: Veeam, Cove, Datto, and cloud backup platforms).
• Confidence with basic AI concepts, especially around security and data and IP governance.
• Comfort working in healthcare-adjacent environments with sensitivity to HIPAA, PHI, and clinical or lab operational constraints.
• Strong troubleshooting, logic, and critical thinking skills.
• Strong written and verbal communication skills, including translating technical issues into plain language for non-technical clinical and administrative staff.
• Self-motivated approach with strong time management and ability to manage multiple priorities in a fast-paced, changing environment.
• Ability to identify and articulate improvement opportunities within client environments.
• Demonstrated ability to mentor and develop junior technicians.
• Commitment to continuous professional development and willingness to achieve technical certifications required for client support.

Education

• Bachelor’s degree in Information Systems, Computer Science, or a related discipline (preferred).

Tools you will work with

Microsoft 365 (Exchange Online, Teams, SharePoint, OneDrive), Entra ID, Active Directory, Intune, GPO, Windows 10/11, MFA, Conditional Access, EDR (including SentinelOne), N-able and N-able RMM, ConnectWise Manage, PSA/RMM, HIPAA/PHI, and examples of networking/security tools and vendors including Meraki, Fortinet, Palo Alto, Veeam, Cove, Datto, Microsoft Defender for Endpoint, Proofpoint, Mimecast, Barracuda, Duo, Okta, DNS, and DHCP.

Compensation and benefits

• Pay range: 33.65 - 38.46 USD per hour (Boston, MA)
• 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