Department: Transportation 

Reports to: Transportation Coordinator 

Position Type: Part-time, Non-exempt

About Westover School

Westover School is a gender-inclusive girls boarding and day school serving grades 9–12, where smart, motivated students become confident, connected adults. We are committed to providing a college preparatory education in a small community atmosphere that emphasizes student-adult interaction. Through our programs and faculty, Westover fosters the confidence and strength each student needs to shape their own life.

We empower students to be themselves, make their own choices, and experience a true sense of belonging—resulting in young adults who lead lives of purpose and meaning and understand the power of relationships.

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.

Responsibilities and Duties

• 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

Required Qualifications & Skills

• Valid Connecticut driver’s license required
• Public Passenger Endorsement (A or V) or willingness to obtain one
• CDL with Passenger (P) Endorsement preferred for operation of larger vehicles, 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 remain calm under varying conditions
• Ability to work a flexible schedule, including evenings and weekends as needed
• Knowledge of local and state traffic laws and safety regulations
• Commitment to confidentiality and student privacy
• Ability to drive for extended periods (up to five hours or more)

Working Conditions

• Work is performed in school vehicles and throughout the local and regional area
• Schedule is flexible and based on transportation needs, including evenings and weekends
• Regular interaction with students, faculty, and families
• Driving may occur in varying weather and traffic conditions

Physical Requirements

• Ability to sit and drive for extended periods of time
• Ability to assist with minor vehicle-related tasks as needed
• Ability to lift up to 25 pounds

Compensation & Benefits

This is a part-time, non-exempt position. Compensation is based on an hourly rate commensurate with experience.

Equal Employment Opportunity Statement

Westover School is an Equal Opportunity Employer and does not discriminate on the basis of race, color, religion, national or ethnic origin, sex, sexual orientation, gender identity or expression, age, disability, veteran status, or any other characteristic protected by applicable law. We are committed to building a diverse and inclusive community and strongly encourage candidates from historically underrepresented backgrounds to apply.

About Westover School

Westover School is an all-girls' boarding and day school, grades 9-12 where smart, motivated girls become confident, connected women. We are committed to providing a college preparatory education in a small community atmosphere that emphasizes student-adult interaction. Westover, through program and faculty, endeavors to develop in each student the confidence and strength to shape her own life - to become the best that she can be. We celebrate diversity of all kinds and are committed to creating an inclusive culture built on a foundation of respect for all individuals. We seek to hire, develop and retain talented people from all backgrounds. Individuals from non-traditional backgrounds, historically marginalized or underrepresented groups are strongly encouraged to apply. Westover School is located in Middlebury, CT; 45 minutes from New Haven, 1 1/2 hours from New York City, and 2 hours from Boston. For more information, please visit our website at www.westoverschool.org. Westover School is an Equal Opportunity Employer. Application Notes: Interested candidates should address these aforementioned qualifications and skills in their cover letter in addition to providing a résumé. Please see the employment page at westoverschool.org.

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