Job Title: Driver

Department: Transportation

Location: Westover School – Middlebury, CT

Status: Part-time, Non-exempt

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. All drivers should have a clean driving record and be able to pass criminal background and drug screenings.

Key Responsibilities

• Coordinate daily driving assignments with the Transportation Coordinator; adapt to any scheduling or route changes.
• Conduct pre-trip safety inspections, including checks of brakes, lights, horn, windshield wipers, emergency equipment, and overall vehicle condition.
• Operate school vehicles responsibly to ensure the safe and timely transport of students.
• Refuel, clean, and return vehicles to the designated parking area after use; record mileage and complete a final inspection.
• Report any maintenance issues or vehicle damage immediately to the Transportation Coordinator.
• Follow all procedures in the event of an accident, including contacting emergency services, administering first aid if needed, and completing required incident reports.
• Maintain a valid Connecticut driver’s license and the appropriate Public Passenger Endorsement (e.g., A or V) or a CDL with Passenger Endorsement, as applicable.
• Demonstrate professionalism, courtesy, and strong customer service when interacting with students, faculty, staff, and families.

Required Skills and Qualifications:

• A valid Connecticut driver’s license with a Public Passenger Endorsement (e.g., A or V) is required for student transportation; alternatively, a CDL with Passenger (P) Endorsement is acceptable and preferred for operation of larger-capacity vehicles.

• Clean driving record and ability to pass background checks and drug screenings.
• Familiarity with vehicle safety checks and routine maintenance procedures.
• Ability to remain calm, alert, and courteous under varying driving conditions.
• Excellent communication skills—both verbal and written.
• Ability to work a flexible, irregular schedule including evenings and weekends as needed.
• Knowledge of local and state traffic laws and safety regulations.
• Commitment to maintaining confidentiality and upholding student privacy at all times.
• Physical ability to drive for periods exceeding five hours and assist with minor vehicle-related duties.

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.

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 that does not discriminate on the basis of actual or perceived race, creed, color, religion, alienage or national origin, ancestry, citizenship status, age, intellectual or physical disability, sex, marital status, veteran status, sexual orientation, transgender identity or status, genetic information, or any other characteristic protected by applicable federal, state or local laws. We celebrate the 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.