School Transportation Driver (Flexible Part-Time)

Westover School, Incorporated; Middlebury (CT); On-site; USD 25,000 - 36,000; Part time

Benefits offered by this job

Hourly pay commensurate withexperience

Job summary

Westover School is seeking detail-oriented and dependable drivers to support student transportation needs. Drivers are responsible for safely transporting students to and from appointments, athletic events, and school-related activities within Middlebury and surrounding areas.

This is a flexible, part-time position with hours scheduled on an as-needed basis. The ideal candidate demonstrates a strong commitment to student safety, professionalism, and reliability.

Qualifications

• Valid Connecticut driver’s license is required.
• Public Passenger Endorsement (A or V) or willingness to obtain one.
• CDL with Passenger Endorsement (P) is preferred but not required.
• Clean driving record and ability to pass background checks and drug screenings.
• Familiarity with vehicle safety checks and routine maintenance.
• Strong communication skills and ability to stay calm under varying conditions.
• Flexible schedule including evenings and weekends.
• Knowledge of local and state traffic laws and safety regulations.
• Commitment to confidentiality and student privacy.
• Ability to drive extended periods (up to five hours or more).

Responsibilities

• Coordinate daily driving assignments with the Transportation Coordinator and adapt to schedule or route changes as needed
• Conduct pre-trip safety inspections, including brakes, lights, horn, windshield wipers, emergency equipment, and overall vehicle condition
• Safely operate school vehicles to ensure timely and secure transport of students
• Refuel, clean, and return vehicles to designated parking areas; record mileage and complete post-trip inspections
• Report maintenance issues, safety concerns, or vehicle damage promptly
• Follow established procedures in the event of an accident, including contacting emergency services and completing required reports
• Maintain all required licenses and endorsements for assigned vehicles
• Demonstrate professionalism, courtesy, and strong customer service when interacting with students, families, and colleagues

Skills

Valid CT license

Public Passenger Endorsement (A/V)

CDL with Passenger Endorsement (P) – 0

Clean driving record

Background checks & drug screenings

Vehicle safety checks

Strong communication

Flexible schedule (evenings/weekends)

Knowledge of traffic laws

Confidentiality & student privacy

Extended driving periods

Job description

Westover School is seeking detail-oriented and dependable drivers to support student transportation needs. Drivers are responsible for safely transporting students to and from appointments, athletic events, and school-related activities within Middlebury and surrounding areas.

This is a flexible, part-time position with hours scheduled on an as-needed basis. The ideal candidate demonstrates a strong commitment to student safety, professionalism, and reliability.