About HealthDrive 

HealthDrive delivers 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 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. 

Work Environment

Works within policies of HealthDrive. Based at HealthDrive's Framingham, MA office on a hybrid schedule. Occasional travel to company locations may be required to support infrastructure work, office technology needs, mergers and acquisitions activities, or other business priorities. 

This role participates in after-hours activity 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.

Compensation

$26.44 to $36.05 hourly, based on experience 

What's in It for You

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

#INDHDCORPREC

Key Responsibilities

• • Second-line resolution: Resolve escalated incidents and requests across applications, systems and end-user support, taking ownership through to closure rather than routing work onward. 

• • Application support: 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. 

• • Identity and access administration: 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. 

• • Microsoft 365 tenant support: Administer Exchange Online mailboxes, shared mailboxes, distribution lists, mailbox permissions and delegation. Manage licence assignment and reclamation. 

• • Endpoint management: Support Intune configuration profiles, compliance policies and Autopilot enrolment. Administer mobile device management for the corporate handset fleet. 

• • Network and connectivity: 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. 

• • Server services: Support remote desktop and terminal services, print services and fax services, and respond to capacity and error conditions. 

• • End-user support: 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. 

• • First responder rotation: Take scheduled rotation weeks covering intake, triage and first-contact resolution across all support categories. 

• • Automation and self-service: 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. 

• • Service level performance: Meet resolution targets and lead times, and work queued requests to schedule rather than allowing routine changes to age. 

• • Documentation: Author and maintain runbooks, standard operating procedures and 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, including timely removal of access at departure. 

• • Security agent health: 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. 

• • Cross-functional coordination: Work with infrastructure engineering, the Security function, application engineering and the Primary Care support lead on issues that span boundaries.

Required Qualifications

• 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. 

Preferred Qualifications

• 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. 

Education & Qualifications

• Bachelor's degree in Information Technology, Computer Science, Information Systems or a related field 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 than working a single specialist queue. 

• Demonstrated experience owning an area of technical responsibility, including its documentation.

Certifications & Licenses

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

Good to have 

• Microsoft 365 Certified: Administrator Expert, or Endpoint Administrator Associate. 

• Microsoft Certified: Identity and Access Administrator Associate. 

• CompTIA Network+ or Security+. 

• ITIL Foundation Certification.