IT Support Specialist II

HealthDrive is building a stronger support experience for clinical and business teams, and the IT Support Specialist II role is a senior individual contributor position on the IT support team. You will provide second-line, end-to-end resolution across Microsoft 365 and identity services, endpoint and device management, connectivity, and day-to-day user support, with primary depth in Microsoft 365 tenant and identity administration. The role also includes participation in an after-hours/first-responder rotation for critical incidents and planned tenant work.

Location and schedule: Framingham, MA (hybrid). Pay: USD 26 - 36 per hour. Experience: 4+ years in progressive IT support.

What you’ll do

• Handle escalated incidents and requests across applications, systems, and end-user support, owning items through to closure instead of routing them onward.
• Troubleshoot HealthDrive electronic medical record platforms, Practice Management Suite, facility platforms, and business applications, including record maintenance and data corrections with query-level diagnostics when needed.
• Administer accounts, groups, and role assignments in Entra ID and Active Directory; manage access requests, support multi-factor authentication enrolment and re-registration, and troubleshoot conditional access outcomes.
• Administer Exchange Online mailboxes, shared mailboxes, distribution lists, mailbox permissions, and delegation; manage licence assignment and reclamation.
• Support Intune configuration profiles, compliance policies, and Autopilot enrolment; administer mobile device management for the corporate handset fleet.
• Diagnose wired, wireless, and remote access issues, including VPN connectivity plus TCP/IP, DNS, and DHCP faults; escalate genuine infrastructure defects with diagnostic work already completed.
• Support remote desktop and terminal services, print services, and fax services, including responses to capacity and error conditions.
• Share steady support volume for endpoint and peripheral faults, OS behaviour, single-user connectivity and printing, and routine access requests as a standing part of the role.
• Participate in scheduled rotation weeks covering intake, triage, and first-contact resolution across all support categories.
• Use PowerShell and Microsoft Graph to script recurring administrative requests, focusing on high-frequency, low-complexity items to reduce manual queue handling.
• Meet resolution targets and lead times by working queued requests to schedule rather than allowing routine changes to age.
• Author and maintain runbooks, standard operating procedures, and knowledge base articles; receive and document scheduled knowledge transfer from existing team members.
• Complete joiner and leaver identity, licensing, access, and application tasks to defined lead times, including timely access removal at departure.
• Verify endpoint management and security agents are installed and reporting, and remediate failed agents while keeping policy configuration and alert response with the Security function.
• Collaborate with infrastructure engineering, Security, application engineering, and the Primary Care support lead on cross-boundary issues.

What you bring

• 4+ years of progressive IT support experience, including second-line or escalation responsibility in a business environment.
• Breadth across domains: the ability to resolve application, systems, and end-user issues rather than focusing on a single specialist queue (this replaces a generalist).
• Demonstrable Microsoft 365 administration experience, including Exchange Online (mailboxes and shared mailboxes), distribution lists, permissions/delegation, and licence management.
• Working administration of Entra ID and Active Directory, including accounts and groups, multi-factor authentication, and practical understanding of conditional access.
• Experience supporting business or clinical applications, including user access, roles, and workflow troubleshooting.
• PowerShell scripting for repetitive administration, with willingness to work with Microsoft Graph as central to the role.
• Networking fundamentals to diagnose connectivity and remote access issues, plus DNS and DHCP, with the ability to escalate using evidence.
• Experience with Intune (configuration profiles, compliance policies, and device enrolment).
• Experience working within an ITSM platform, including ticket lifecycle, queue management, and lead-time discipline.
• Documentation discipline, including a track record of writing runbooks or procedures that others successfully use.
• Clear communication with clinical and non-technical users, including providers, field staff, and corporate employees.

Benefits

• PPO Medical, Dental, and Vision Insurance
• 401(k) + Company match
• Paid Time Off
• Employee referral bonuses

Additional notes

• Occasional travel may be required to support infrastructure work, office technology needs, mergers and acquisitions activities, or other business priorities.
• After-hours activity may be required for critical incidents, planned changes, tenant migrations, and acquisition cutovers.
• The role may require lifting, transporting, or setting up end-user and network equipment as needed.

Technologies you’ll work with

• Microsoft 365, Exchange Online, Entra ID, Active Directory
• Multi-factor authentication, conditional access
• PowerShell, Microsoft Graph
• Intune, Autopilot
• VPN, TCP/IP, DNS, DHCP
• Remote desktop, terminal services
• Print services, fax services
• ITSM platform

Preferred qualifications

• Experience in healthcare or another regulated environment, including working awareness of HIPAA and protected health information handling.
• Experience supporting electronic medical record or practice management systems.
• SQL familiarity sufficient to read and adapt queries for diagnostics and record verification.
• Windows Server support experience, including remote desktop or terminal services and print services.
• Experience administering a cloud-managed network platform such as Meraki.
• Experience reducing ticket volume through self-service (example: self-service password reset or a request catalogue).
• Experience supporting distributed, field-based, or multi-site users.
• Familiarity with endpoint security and management tooling, including agent deployment and health troubleshooting.

Education & certifications

• Bachelor’s degree in Information Technology, Computer Science, Information Systems, or a related field preferred; equivalent practical experience considered.
• No certifications or licenses required.
• Favorably considered (not screening criteria): Microsoft 365 Certified: Administrator Expert or Endpoint Administrator Associate; Microsoft Certified: Identity and Access Administrator Associate; CompTIA Network+ or Security+; ITIL Foundation Certification.