IT Support Specialist II

HealthDrive•Framingham, MA

2d•Hybrid

About The Position

The IT Support Specialist II is a senior individual contributor on HealthDrive's IT support team, responsible for second-line resolution across the full support portfolio: clinical and business applications, Microsoft 365 and identity services, endpoint management, network connectivity, and day-to-day end-user support. This is a broad delivery role rather than a narrow specialism. Within that breadth, the role carries designated depth in Microsoft 365 tenant and identity administration. That capability is thinly held on the team today, and the role is the primary resolver for tenant, identity, access and connectivity work that would otherwise escalate outside the support function. A substantial share of the work in this area is repetitive administration rather than complex engineering. The role is therefore expected to reduce recurring demand through scripting, self- service and permanent fixes rather than to absorb it indefinitely, and to convert individually held knowledge into maintained runbooks. The Specialist II participates in the team's first responder rotation and carries general end-user support volume alongside their area of depth.

Requirements

Four or more years of progressive IT support experience, including second-line or escalation responsibility in a business environment.
Genuine breadth: demonstrated ability to resolve application, systems and end-user issues rather than depth in a single domain only. This role replaces a generalist and requires range.
Demonstrable Microsoft 365 administration: Exchange Online, mailboxes and shared mailboxes, distribution lists, permissions and delegation, and licence management.
Working administration of Entra ID and Active Directory, including accounts, groups, multi-factor authentication and a practical understanding of conditional access.
Experience supporting business or clinical applications, including user access, roles and workflow troubleshooting.
Scripting for repetitive administration using PowerShell, and willingness to work with Microsoft Graph. This is central to the role rather than incidental.
Networking fundamentals sufficient to diagnose connectivity, remote access, DNS and DHCP problems and to escalate with evidence.
Experience with Microsoft Intune, including configuration profiles, compliance policies and device enrolment.
Experience working to service levels within an ITSM platform, including ticket lifecycle, queue management and lead-time discipline.
Documentation discipline: a track record of writing runbooks or procedures that other people successfully use.
Ability to communicate clearly with clinical and non-technical users, including providers, field staff and corporate employees.
Minimum of four years of progressive IT support experience, with at least two years including Microsoft 365 and identity administration.
Demonstrated experience carrying sustained ticket volume across multiple domains rather than working a single specialist queue.
Demonstrated experience owning an area of technical responsibility, including its documentation.

Nice To Haves

Experience in healthcare or another regulated environment, with 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, including 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.
Bachelor's degree in Information Technology, Computer Science, Information Systems or a related field preferred; equivalent practical experience considered.
Microsoft 365 Certified: Administrator Expert, or Endpoint Administrator Associate.
Microsoft Certified: Identity and Access Administrator Associate.
CompTIA Network+ or Security+.
ITIL Foundation Certification.

Responsibilities

Resolve escalated incidents and requests across applications, systems and end-user support, taking ownership through to closure rather than routing work onward.
Troubleshoot HealthDrive's electronic medical record platforms, Practice Management Suite, facility platforms and business applications. Perform record maintenance and data corrections, including query-level diagnostics where required.
Administer accounts, groups and role assignments in Entra ID and Active Directory. Fulfil 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 problems, including VPN connectivity and 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, and respond to capacity and error conditions.
Carry general support volume — endpoint and peripheral faults, operating system behaviour , single-user connectivity and printing, and routine access requests — as a standing part of the role rather than as overflow.
Take scheduled rotation weeks covering intake, triage and first-contact resolution across all support categories.
Script recurring administrative requests using PowerShell and Microsoft Graph. Identify high-frequency, low-complexity request types and remove them from the queue rather than fulfilling them manually.
Meet resolution targets and lead times, and work 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 knowledge transfer from existing team members on a scheduled basis.
Complete identity, licensing, access and application tasks for joiners and leavers to defined lead times, including timely removal of access at departure.
Verify that endpoint management and security agents are installed and reporting, and remediate failed agents on endpoints. Policy configuration and alert response remain with the Security function.
Work with infrastructure engineering, the Security function, application engineering and the Primary Care support lead on issues that span boundaries.