Assistant Director of Technology

The Assistant Technology Specialist supports Yankee Line’s technology infrastructure, with a focus on frontline user support and maintaining technology systems installed in the company’s vehicle fleet.

User Support: Provide Tier 1–2 helpdesk support to staff across four company sites. Troubleshoot common issues with computers, printers, phones, and Office 365 apps. Set up and configure new employee workstations (hardware and software). Provide in-person support and training for basic technology use.

Fleet Technology: Install and maintain onboard vehicle technology. Assist in troubleshooting and replacing failed vehicle hardware. Perform regular fleet tech audits and repairs as needed. Travel to off-site locations for installations and support.

Device and Inventory Management: Maintain and update asset inventory (laptops, tablets, phones, fleet tech, etc.). Assist in lifecycle management: equipment prep, deployment, and retirement. Document installations, repairs, and changes in company systems.

Administrative & Technical Support: Escalate unresolved issues to the Director of Technology. Maintain documentation for recurring processes and equipment standards. Support Intune-based enrollment and configuration of devices under guidance. Assist with user onboarding/offboarding tasks as assigned.

Preferred Qualifications: Familiarity with Windows operating systems, Microsoft 365, and mobile devices. Experience with low-voltage hardware or vehicle electronics is a plus. Strong communication and customer service skills. Basic understanding of Wi-Fi and networking concepts. Comfortable working inside vehicles and using hand tools. Ability to lift up to 40 pounds and work in confined vehicle spaces. Valid driver’s license and willingness to travel to satellite offices or garages. Ability to pass an FMCSA medical examination.

Work Conditions: Primarily on-site with fieldwork required at fleet locations. Available to work (24) hours per day, (7) days per week during emergencies or any other circumstance that may potentially impact service. Occasional evening or weekend work depending on fleet schedules. Reports directly to the Director of Technology.