JOB DETAILS

Technical Support Specialist

CompanyCorporate Transportation Group
LocationGlen Allen
Work ModeOn Site
PostedFebruary 26, 2026
About The Company
CTG pushes the boundaries of passenger ground transportation. We run dedicated microtransit operations, manage broker programs, coordinate corporate travel, and deliver NEMT medical transportation—powered by modern tech that streamlines workflows and elevates the experience for riders and drivers. With 30+ years of hands-on operations and a broad U.S. footprint, we combine deep industry expertise with cutting-edge solutions to deliver reliable, accessible, and scalable mobility for organizations and communities. For customers, that means consistent quality and accountability; for talent, it’s a place where transportation pros and technologists solve meaningful problems and grow their careers.
About the Role

Technical Support Specialist

Location: Glen Allen, VA (On-Site)
Company: MediDrive

About MediDrive

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.

Position Overview

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

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.

Key Responsibilities

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

Qualifications

Required:

  • 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

What We Offer

  • Competitive salary

  • Health benefits

  • Growth opportunities within a fast-scaling healthcare technology company

  • Opportunity to work in a mission-driven environment improving healthcare access


Key Skills
TroubleshootingWindowsMacOSTicketing SystemsCommunicationOrganizationAsset InventoryOnboardingOffboardingVPN AccessSaaS SupportHIPAANetworkingDevice Management
Categories
Customer Service & SupportTechnologyHealthcareAdministrative
Benefits
Health benefits
Job Information
📋Core Responsibilities
This role involves providing Level 1 technical support, handling both internal IT issues for employees (workstations, printers, network) and external client-facing assistance (application access, basic troubleshooting). Responsibilities include maintaining employee productivity, accurately documenting all tickets, and escalating complex issues to higher tiers.
📋Job Type
full time
📊Experience Level
2-5
💼Company Size
69
📊Visa Sponsorship
No
💼Language
English
🏢Working Hours
40 hours
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