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AboutHealthDrive

HealthDrivedelivers on-site healthcare services to residents of long-term care facilities, offering a comprehensive suite of specialties including primary care, behavioral health, dentistry, optometry, podiatry, and audiology. Our mission is to improve the quality of life for patients through compassionate and consistent care, while supporting our partners with reliable, integrated healthcare solutions tailored to the unique needs of senior populations.

About the Position

The IT Support Specialist II is a senior individual contributor onHealthDrive'sIT 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,accessand connectivity work that would otherwise elevate 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-serviceand permanent fixes rather than to absorb it indefinitely, and to convert individually held knowledge into maintained runbooks. The Specialist IIparticipatesin the team's first responder rotation and carries general end-user support volume alongside their area of depth.

Works within policies ofHealthDrive. Based atHealthDrive'sFramingham, MA office on a hybrid schedule. Occasional travel to company locations may berequiredto support infrastructure work, office technology needs, mergers and acquisitions activities, or other business priorities.

This roleparticipatesin after-hoursactivity for critical incidents, planned changes, tenantmigrationsand acquisition cutovers. The role may require lifting,transportingor setting up end-user and network equipment as needed.

$26.44 to $36.05 hourly, based on experience

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

#INDHDCORPREC

• Second-line resolution:Resolve escalated incidents and requests across applications,systemsand end-user support, taking ownership through to closure rather than routing work onward.
• Application support:TroubleshootHealthDrive'selectronic medical record platforms, Practice Management Suite, facilityplatformsand business applications.Perform record maintenance and data corrections, including query-level diagnostics where required.
• Identity and access administration:Administer accounts,groupsand role assignments in Entra ID and Active Directory. Fulfil access requests, support multi-factor authentication enrolment and re-registration, and troubleshoot conditional access outcomes.
• Microsoft 365 tenant support:Administer Exchange Online mailboxes, shared mailboxes, distribution lists, mailboxpermissionsand delegation. Managelicenceassignment and reclamation.
• Endpoint management:Support Intune configuration profiles, compliancepoliciesand Autopilot enrolment. Administer mobile device management for the corporate handset fleet.
• Network and connectivity:Diagnose wired,wirelessand remote access problems, including VPN connectivity and TCP/IP,DNSand DHCP faults. Escalate genuine infrastructure defects with diagnostic work already completed.
• Server services:Support remote desktop and terminal services, print services and fax services, and respond to capacity and error conditions.
• End-user support:Carrygeneral supportvolume — endpoint and peripheral faults, operating systembehaviour, single-user connectivity and printing, and routine access requests — as a standing part of the role ratherthan asoverflow.
• First responder rotation:Take scheduled rotation weeks covering intake,triageand first-contact resolution across all support categories.
• Automation and self-service:Script recurring administrative requests using PowerShell and Microsoft Graph.Identifyhigh-frequency, low-complexity request types and remove them from the queue rather than fulfilling them manually.
• Service level performance:Meet resolution targets and lead times, and work queued requests to schedule rather than allowing routine changes to age.
• Documentation:Author andmaintainrunbooks, standard operatingproceduresand knowledge base articles. Receive and document knowledge transfer from existing team members on a scheduled basis.
• Onboarding and offboarding support:Complete identity, licensing, access and application tasks for joiners and leavers to defined lead times, includingtimelyremoval of access at departure.
• Security agent health:Verify that endpoint management and security agents are installed andreporting, andremediate failed agents on endpoints. Policy configuration and alert response remain with the Security function.
• Cross-functional coordination:Work with infrastructure engineering, the Security function, applicationengineeringand the Primary Care support lead on issues that span boundaries.

• Four or more years of progressive IT support experience, including second-line orescalationresponsibility in a business environment.
• Genuine breadth:demonstratedability to resolve application,systemsand end-user issues rather than depth in a single domain only. This role replaces a generalist and requiresrange.
• Demonstrable Microsoft 365 administration: Exchange Online, mailboxes and shared mailboxes, distribution lists, permissions and delegation, andlicencemanagement.
• Working administration of Entra ID and Active Directory, including accounts, groups, multi-factorauthenticationand a practical understanding of conditional access.
• Experience supporting business or clinical applications, including user access,rolesand 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 fundamentalssufficientto diagnose connectivity, remote access,DNSand DHCP problems and to elevate with evidence.
• Experience with Microsoft Intune, including configuration profiles, compliancepoliciesand device enrolment.
• Experience working to service levels within an ITSM platform, including ticket lifecycle, queuemanagementand lead-time discipline.
• Documentation discipline:a track recordof writing runbooks or procedures that other people successfully use.
• Ability to communicate clearly with clinical and non-technical users, including providers, fieldstaffand corporate employees.

• Experience in healthcare or another regulated environment, with working awareness of HIPAA and protected health information handling.
• Experience supporting electronic medicalrecordor practice management systems.
• SQL familiaritysufficientto read and adapt queries for diagnostics and record verification.
• Windows Server support experience, including remote desktop or terminal services and print services.
• Experience administeringa cloud-managed networkplatformsuch as Meraki.
• Experience reducing ticket volume through self-service, including self-service password reset or a request catalogue.
• Experience supporting distributed, field-basedor multi-site users.
• Familiarity with endpoint security and management tooling, including agent deployment and health troubleshooting.

• Bachelor's degree in Information Technology, Computer Science, InformationSystemsora relatedfield preferred; equivalent practical experience considered.
• 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 thanworkinga single specialist queue.
• Demonstrated experience owning an area of technical responsibility, including its documentation.

No certifications or licenses arerequiredfor this role. Demonstrated hands-on capability is weighted well above credentials. The following are considered favorably but are not a screening criterion:

• Microsoft 365 Certified: Administrator Expert, or Endpoint Administrator Associate.
• Microsoft Certified: Identity and Access Administrator Associate.
• CompTIA Network+ or Security+.
• ITIL Foundation Certification.