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.
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.