IT Helpdesk Supervisor

About the Role

The IT Helpdesk Supervisor leads HealthDrive's IT Helpdesk function, ensuring effective delivery of technology support services across clinical and corporate operations. This role supervises a team of IT Support Engineers and oversees support for HealthDrive's current electronic medical record systems, Practice Management Suite, business applications, endpoint devices, Microsoft 365 services, and office technology. The IT Helpdesk Supervisor manages day-to-day Helpdesk operations through Freshdesk, including ticket prioritization, workload balancing, escalation management, service level performance, and continuous process improvement. The role coordinates technology onboarding for new employees and providers, as well as mergers, acquisitions, and organizational growth initiatives.

Responsibilities

• Lead the daily operation of the IT Helpdesk, including ticket review, prioritization, assignment, escalation, and follow-through to resolution.
• Supervise, coach, and mentor a team of 4+ IT Support Engineers responsible for end-user support across HealthDrive.
• Ensure the team is working on the right tickets at the right time based on business impact, urgency, service levels, and operational priorities.
• Monitor Helpdesk queues, backlog, aging tickets, escalations, and service level performance using Freshdesk.
• Serve as the first-line escalation point for complex, high-priority, or time-sensitive user support issues.
• Oversee support for HealthDrive's current EMR systems, Practice Management Suite, and other operational business applications.
• Coordinate support for laptops, mobile phones, printers, peripherals, conference room technology, software access, and other office technology needs.
• Ensure end-user devices are provisioned, replaced, tracked, and supported according to organizational standards.
• Coordinate technology onboarding for new staff, including account provisioning, device preparation, software setup, and technology orientation/setup calls.
• Coordinate technology setup for new providers, ensuring devices, access, applications, and support readiness are in place prior to go-live or patient care activities.
• Coordinate Helpdesk-related technology onboarding for acquired groups, new facilities, and organizational expansion efforts, including users, devices, applications, and support processes.
• Partner with HR, Recruiting, Credentialing, Operations, Infrastructure, Security, Business Applications, and hiring managers to ensure timely and complete onboarding and support delivery.
• Develop and maintain Helpdesk workflows, standard operating procedures, onboarding checklists, and knowledge base articles.
• Track and report on ticket volume, backlog, aging, resolution times, service levels, recurring issues, and team performance.
• Identify opportunities to improve service quality, reduce recurring issues, streamline onboarding, and increase Helpdesk efficiency.
• Promote a responsive, professional, and accountable support culture focused on high-quality service to providers, field staff, and corporate employees.

Requirements

• Bachelor's degree in Information Technology, Computer Science, Information Systems, Business, or a related field preferred.
• Minimum of 5 years of progressive IT support, Helpdesk, service desk, or end-user support experience.
• Minimum of 2 years of supervisory, team lead, or people management experience in an IT support environment.
• Demonstrated experience managing support queues, ticket priorities, escalations, and day-to-day service delivery.
• Experience supporting distributed teams, field-based users, providers, or multi-location business environments preferred.

Qualifications

• Strong leadership, coaching, prioritization, and team development skills.
• Experience supervising or leading IT support, Helpdesk, service desk, or end-user support teams.
• Strong understanding of IT service management principles, ticket lifecycle management, incident management, and service request fulfillment.
• Experience using an ITSM platform such as Freshdesk, Freshservice, ServiceNow, Jira Service Management, or a comparable tool.
• Strong ability to manage competing priorities, assign work effectively, and keep the team aligned to business needs.
• Experience supporting endpoint devices, laptops, mobile phones, printers, Microsoft 365, and common business applications.
• Ability to communicate clearly with technical and non-technical users, including providers, field staff, operations leaders, and corporate employees.
• Strong troubleshooting, documentation, follow-up, and customer service skills.
• Experience coordinating user onboarding, account provisioning, device setup, and technology readiness activities.
• Ability to work cross-functionally with IT, HR, Operations, Credentialing, and business stakeholders.
• Experience in healthcare IT or a multi-site healthcare services organization (nice to have).
• Experience supporting EMR systems, practice management systems, or healthcare operations applications (nice to have).
• Experience coordinating technology onboarding for mergers, acquisitions, facility openings, or large user groups (nice to have).
• Experience developing Helpdesk metrics, operational dashboards, SOPs, and knowledge base content (nice to have).
• Familiarity with ITIL principles or formal service delivery frameworks (nice to have).
• Experience with hardware asset management, software deployment tools, or endpoint management platforms (nice to have).

Skills

• Communication
• Cooperation and Teamwork
• Customer Focus
• Leadership and Team Development
• Service Excellence
• Accountability
• Prioritization and Execution
• Problem Solving / Analysis
• Adaptability
• Process Improvement
• Operational Excellence
• Change Management

Benefits

• PPO Medical, Dental, and Vision Insurance
• 401(k) with company match
• Paid Time Off
• Lunch program
• Hybrid schedule opportunity
• Verizon Wireless, Dell, and other employee discounts
• Profit sharing
• Employee referral bonuses

Pay

$54,000 to $80,000, depending on experience, skill set, and proven track record.

Schedule

Hybrid schedule based at HealthDrive's Framingham, MA office (off Route 9, near Routes 90 and 495). Occasional travel to company locations may be required. This role may occasionally participate in after-hours support activities for critical incidents, onboarding events, acquisitions, or organizational initiatives.

Work Environment

The role may require lifting, transporting, or setting up end-user technology equipment as needed.