At Gifthealth, we're revolutionizing the way people experience healthcare by simplifying the process of managing prescriptions and health services. Our mission is to provide a seamless, personalized, and efficient healthcare experience for all our customers. We're a dynamic, innovative, and customer-centric company dedicated to making a positive impact on people's lives.

The IT Support Specialist II provides advanced end-user technical support across Gifthealth’s user environment, including workstations, applications, access, connectivity, peripherals, and standard business systems. Reporting to the IT Support Site Lead, this role handles incoming support requests, resolves escalated or moderately complex technical issues, documents work accurately, and coordinates with IT Support, IT Operations, or Engineering when additional support is needed. This position focuses on issue ownership, deeper troubleshooting, effective escalation handling, clear communication, and maintaining a consistent, high-quality support experience that helps reduce unnecessary escalations and maintain user productivity.

• Responds to incoming IT support requests through the ticketing system, chat, and in-person interactions while balancing direct ticket intake with escalated work from IT Support Specialist I.
• Troubleshoots and resolves standard and moderately complex issues involving workstations, applications, access, connectivity, user devices, peripherals, and enterprise support systems.
• Serves as an escalation point for IT Support Specialist I by taking ownership of escalated issues, applying deeper troubleshooting and judgment, documenting user or business impact, and driving resolution whenever possible before escalating to the IT Support Site Lead, IT Operations, Engineering, or other teams.
• Escalates urgent or high-impact issues through established site leadership coverage, IT Support leadership, or designated escalation paths when the assigned IT Support Site Lead is unavailable.
• Maintains response-time, resolution, documentation, escalation, and first-contact resolution expectations aligned with IT Support service standards.
• Identifies recurring issues, support trends, and opportunities to improve workflows, reduce repeat incidents, strengthen root cause analysis, and reduce unnecessary escalations.
• Assists with complex device deployments, upgrades, site-level technology changes, onboarding, offboarding, access workflows, and implementation of solutions directed by IT Support leadership or IT Operations.
• Develops and maintains knowledge base articles, troubleshooting documentation, and standard procedures for complex or recurring issues while providing guidance and mentorship to IT Support Specialist I team members.
• Communicates clearly and professionally with technical and non-technical users, handles escalated or sensitive support issues with accountability, and maintains a high level of customer service.

• Education: High school diploma or equivalent. (Required)
• Licensure/Certification: Intermediate-level IT certification, such as CompTIA Network+, or equivalent experience. (Preferred)
• Experience:
• 2 - 4 years of experience in an IT support, help desk, or technical support role. (Required)
• Experience working in an IT service management system and handling escalated tickets. (Preferred)
• Experience mentoring or supporting junior team members. (Preferred)
• Exposure to identity, endpoint, or enterprise support environments. (Preferred)
• Knowledge, Skills, & Abilities:
• Strong understanding of endpoint systems, user environments, common business applications, peripherals, enterprise support tools, and basic identity/access concepts such as SSO, SAML, provisioning, password resets, and access workflows. (Required)
• Advanced troubleshooting skills with the ability to diagnose and resolve standard and moderately complex technical issues. (Required)
• Ability to manage incoming support volume while owning escalated issues, applying sound judgment, and driving issues through resolution. (Required)
• Ability to analyze problems, identify recurring trends, contribute to root cause resolution, improve support workflows, and reduce unnecessary escalations. (Required)
• Strong documentation and communication skills, including attention to detail, clear escalation context, and the ability to translate technical concepts for non-technical users. (Required)
• Ability to work independently while collaborating across IT Support, IT Operations, Engineering, and business teams and maintaining alignment with team processes, support expectations, and escalation paths. (Required)
• Understanding of data privacy and security best practices, including appropriate handling of sensitive or regulated information, such as PHI/HIPAA environments. (Required)
• Basic scripting or automation experience, such as PowerShell, Bash, or similar. (Preferred)
• Working knowledge of enterprise support tools and platforms such as Okta, Google Workspace, Slack, IT service management platforms, endpoint management/MDM tools, and cloud-based business applications. (Preferred)

Work Environment

• Location: On-site
• Schedule: Standard Gifthealth business hours with participation in an on-call rotation as required; specific schedules may vary based on site and operational needs.

Regular onsite support for end users, devices, workstations, peripherals, and day-to-day technology operations. This role may also interact with IT Support, IT Operations, Engineering, Facilities, and business teams as needed to resolve escalated user and site technology issues.

• Must be able to move throughout the facility to provide onsite technical support.
• Must be able to lift and transport IT equipment up to approximately 50 lbs.
• Must be able to work on a computer for extended periods.
• Must be able to communicate effectively with users, team members, and leadership in person, over the phone, and via written communication.

Status: Full-time
FLSA: Exempt

Gifthealth is an Equal Opportunity Employer and prohibits discrimination and harassment of any kind. All employment decisions are made without regard to race, color, religion, sex, sexual orientation, gender identity, transgender status, national origin, age, disability, veteran status, or any other legally protected status.

We celebrate diversity and are committed to creating an inclusive environment for all employees. If you do not meet every requirement but still feel you would be a great fit for this role, we encourage you to apply!

This job description is intended to describe the general nature and level of work being performed. It is not intended to be an exhaustive list of all responsibilities, duties, or skills required of personnel. Gifthealth reserves the right to modify job duties or descriptions at any time.