Driver, Part-Time

Middlebury, CT


Part-Time Driver

School Information:

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 their own life.

We are EMPOWERING students to be themselves, to make their own choices, and to appreciate diversity, resulting in young adults who find lives of purpose and meaning, who understand they can make a difference, and who understand the power of relationships.

  • Do you find joy and passion in working with adolescents?

  • Do you put students at the center of their personal development and planning for the future?

  • Does your leadership demonstrate engagement in and a commitment to diversity, equity and inclusion?

Westover School is looking for detailed-oriented drivers to drive students to and from their appointments, sports matches, and social events in Middlebury and the surrounding area and states. Experience preferred but not necessary. Hours are flexible and generally are provided on an as-needed basis. Looking to hire 1 night/weekend driver. All drivers should have a clean driving record and be able to pass criminal background and drug screenings.


  • Check with Transportation Coordinator at scheduled departure time to coordinate any changes in the day’s assignments and adjust route accordingly.

  • Perform vehicle operation and safety check logs on a daily basis, ensuring that the vehicle/bus is in good working order. Walk around the vehicle to visually observe any defects and check operating system – brakes, horn, windshield wipers, lights, first aid kits and emergency flashers before starting trip. 

  • Operate the vehicle in a responsible manner at all times to ensure students arrive safely to their destination.

  • Upon completion of your trip schedule for the day, fuel the vehicle in use and return vehicle to designated parking area. Document all mileage and make a final inspection of the vehicle outside body and inner seating and floor areas. Ensure the inside and outside of the vehicle is clean and in a well-kept manner. Lock vehicle and return keys to designated area.

  • Report any vehicle maintenance needs to the Transportation Coordinator immediately.

  • Report traffic accidents immediately to the Transportation Coordinator and other designated staff members. Request police or ambulance service as needed. Assist injured persons from first-aid kit until these services arrive. Complete and submit accident report within the required time frame per Connecticut State Law. A copy of report shall be provided to the Transportation Coordinator.

  • Maintain an A endorsement or CDL (whichever your position requires) license and any other required trainings. Immediately report any changes in driving status or insurability to the Transportation Coordinator.

  • Demonstrate above average customer service, professional conduct, patience, and tact when driving students.


  • Knowledge of vehicle operation and maintenance. Capable of driving a passenger vehicle, under all types of weather conditions and traffic situations, ensuring the safety of the passengers. Able to drive with confidence.

  • Ability to communicate effectively by following and interpreting oral and written instructions, and collecting information. Must be able to interpret instructions, gather information, and submit reports. Must keep accurate records for vehicle and time sheets.

  • Demonstrative ability to communicate in a clear and concise manner in verbal and written form.

  • Ability to work an irregular schedule in order to meet the transportation needs, of the school and students.

  • Knowledge of Connecticut state and local motor vehicle laws and regulations.

  • Ability to maintain strict confidentiality of records and information pertinent to the nature of the work. Must maintain strict confidentiality of medical information and adhere to Privacy Act requirements.

  • Ability to maintain a safe atmosphere for students during the transportation period.

  • Must be able to drive longer than a 5 hour period.

  • Must be willing to attend mandatory trainings as well as submit to, pass, and maintain driving certification courses when offered.


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

Application Notes:

Interested candidates should address these aforementioned qualifications and skills in their cover letter in addition to providing a résumé.

Westover School is an Equal Opportunity Employer.