Road Supervisor (CDL)

First Student•Hartford, CT

12d•Hybrid

About The Position

At First Student, our Road Supervisors play a critical role in supporting safe and reliable transportation operations. This position serves as a direct support partner to drivers, operations, safety, and local management by ensuring operational compliance, coaching drivers in the field, responding to incidents, and maintaining strong customer service relationships throughout the community. This is an excellent opportunity for an experienced transportation professional who thrives in a fast-paced environment and enjoys a balance of field operations, safety oversight, training, and leadership responsibilities. As a Road Supervisor supporting CREC Schools, you will support daily transportation operations by monitoring driver performance, responding to service and safety concerns, conducting field observations, and assisting with operational and DOT compliance functions. This role combines transportation operations, employee coaching, field safety oversight, training responsibilities, and customer service support.

Requirements

High school diploma or equivalent required
Valid CDL required
Strong communication and interpersonal skills
Comfortable interacting with drivers, customers, senior leadership, union representatives, and the public
Strong organizational and time-management skills
Working knowledge of Microsoft Word, Excel, and PowerPoint
Basic understanding of vehicle maintenance and mechanical processes
Ability to work extended hours as operational needs require, including occasional Saturdays
Must maintain regular and reliable attendance
Must possess reliable transportation within the service area as needed

Nice To Haves

2–3 years of transportation or transit supervisory experience preferred
Experience supervising hourly employees preferred
Human resources, coaching, or training experience preferred

Responsibilities

Communicate job expectations, responsibilities, and operational updates to drivers
Support day-to-day scheduling, driver counseling, and performance evaluations
Conduct on-scene accident investigations and assist with accident documentation and OSHA reporting
Deliver driver safety training, retraining, and behind-the-wheel coaching
Observe drivers in the field and document safety concerns or violations
Respond to customer service concerns and act as liaison between drivers, clients, and management
Monitor driver safety, attendance, compliance, and overall performance
Assist with DOT/FTA compliance, drug testing coordination, and recordkeeping
Support dispatch operations, driver coverage, interviews, and operational administrative tasks as needed
Periodically operate company vehicles and maintain required CDL qualifications
Assist operations leadership with day-to-day service reliability and safety initiatives