Technical Support Specialist

MediDrive is seeking an Technical Support Specialist to support our Glen Allen, VA office and provide Level 1 technical support to our employees.

This role combines internal IT support with external client-facing technical assistance. You will be responsible for maintaining employee productivity, troubleshooting workstation and device issues, assisting clients with application access and basic troubleshooting, and ensuring tickets are properly documented and escalated when needed.

You will serve as the first line of defense for technical issues across the organization., Internal IT Support (Office-Based)

• Provide on-site technical support for employees (Windows, macOS, printers, monitors, peripherals)
• Configure and deploy laptops and workstations
• Assist with onboarding and offboarding (account setup, device provisioning, access control)
• Troubleshoot network connectivity, VPN access, and email issues
• Manage and maintain conference room equipment
• Coordinate with vendors for hardware procurement and repair
• Maintain IT asset inventory and documentation
• Ensure systems comply with company security standards

Client-Facing Level 1 Support

• Respond to inbound technical support requests from clients
• Assist users with:
• Downloading and installing mobile or web applications
• Clearing browser cache and cookies
• Password resets
• Basic troubleshooting steps
• Device compatibility questions
• Log and document all tickets accurately in the support system
• Escalate complex issues to Level 2 / Engineering teams
• Follow up with clients to ensure resolution and satisfaction

• 2-5 years of IT support or help desk experience
• Strong troubleshooting skills (Windows, macOS, browsers)
• Experience with ticketing systems (Jira, Zendesk, Freshdesk, etc.)
• Excellent communication skills (clear, patient, professional)
• Ability to work on-site in Glen Allen, VA
• Strong organizational skills and attention to detail

Preferred:

• Experience supporting SaaS applications
• Familiarity with HIPAA or healthcare technology environments
• Basic networking knowledge (DNS, DHCP, VPN concepts)
• Experience with device management tools (Intune, MDM, etc.)

Key Traits for Success

• Calm under pressure
• Process-driven
• Strong documentation habits
• Customer-service mindset
• Takes ownership of issues
• Proactive, not reactive

• Competitive salary
• Health benefits
• Growth opportunities within a fast-scaling healthcare technology company
• Opportunity to work in a mission-driven environment improving healthcare access

MediDrive is a healthcare technology company delivering transportation management solutions to health plans, providers, and transportation partners nationwide. We operate mission-critical systems that support patient transportation and healthcare access. Reliability, security, and responsiveness are essential to our success.