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Dexter Southfield School offers boys and girls from Pre-Kindergarten through Class 12 a classical education. Our 36-acre campus is located in South Brookline on the Boston-Brookline line, with easy access to Boston. Dexter Southfield offers a collaborative, community atmosphere and excellent benefits.

Dexter Southfield seeks to attract faculty and staff who will uphold the work and values of the School in order to strengthen the community of students, parents, faculty, and staff. Successful candidates will have a commitment to being in and supporting a community which focuses on the education and well-being of students in a variety of settings both in and outside the classroom.

Meet our Faculty and Staff 

Interested candidates should download the printable PDF employment application and submit this completed application, along with a cover letter, a resume and salary requirements, to:
Human Resources
Dexter Southfield
20 Newton Street
Brookline, MA 02445-7498
No phone calls, please.


Dexter Southfield, Inc. (“Dexter Southfield” or the “School”) is an Equal Opportunity Employer. The School offers equal employment opportunity to all applicants for employment and all employees without regard to sex, pregnancy or pregnancy-related condition, sexual orientation, gender identity, age, race, color, religion, national origin, ancestry, veteran status, military service, application for military service, physical or mental disability, genetic information, or any other status protected by applicable law. An applicant who does not meet the minimum qualifications of the position(s) for which the applicant applies will not be considered for employment. If you need a reasonable accommodation to complete this application, interview for the position, or otherwise participate in the hiring process, please notify us.

School Bus Driver (Morning / Afternoon Runs)

About Dexter Southfield

Dexter Southfield is an independent school where boys and girls in Pre-K through Class 12 develop their individual talents and build an ethical foundation for life. Through a classical education and innovative programming, students learn to lead with confidence and serve with compassion. Our 36-acre campus is located on the Brookline-Boston line, just minutes from the city’s best museums, libraries, hospitals, performing arts venues, colleges, and universities—all of which serve as an extension of our classrooms. At Dexter Southfield, we approach everything we do with enthusiasm and commitment, living by our School’s motto: “Our Best Today, Better Tomorrow.”

About You

As a member of our Operations team, you will play an important role in the educational journey of our students, ensuring each is picked up and dropped off at designated bus stops and safely transported to school, sporting events, and other activities. Drivers are expected to maintain the cleanliness, organization, and safety of his/her buses to provide a safe environment for our students. Our fleet of 18 buses cover Boston and surrounding areas including Belmont, Hingham, Charlestown, and Downtown Boston. You enjoy the rhythm and energy of an independent day school and demonstrate integrity, humor, and sound judgment in everything you do.

To be successful in this role, you must be able to:

  • Safely and courteously drive bus and complete assigned routes in all weather conditions
  • Perform pre- and post-route bus inspections in accordance with School policy
  • Comply with all traffic regulations and School driving policies and procedures
  • Follow all safety rules and School policies for children boarding and exiting buses
  • Maintain a clean and mechanically sound bus, reporting problems in a timely manner
  • Notify Transportation Manager in a timely manner of bus maintenance requests/needs
  • Report delays, accidents or other traffic and transportation issues using two-way radio.
  • Submit documentation to Transportation Manager in a timely and professional manner
  • Attend all required meetings and trainings sessions
  • Maintain a clean driving record while employed by School
  • Other duties as assigned by the Head of School or his/her designee
  • Other duties, as assigned.


Skills and Qualifications

  • Hold current commercial driver’s license (CDL) with Passenger (P) and School Bus (S) endorsements
  • Successfully pass required Massachusetts Registry of Motor Vehicles written exams
  • Maintain school bus driver certification by Massachusetts Department of Public Utilities
  • Ability to interact and effectively communicate with children, families and colleagues.
  • First Aid, CPR, and AED certified by a nationally recognized organization
  • Ability to physically lift and assist a child during bus evacuations or emergencies
  • Clean driving record (with no at-fault traffic accidents or citations in the last 5 years)
  • At least one year of driving a school bus required (training provided for the right candidate)
  • Successfully complete pre-employment background screenings, including: CORI, SORI, fingerprinting, driving record, license verification, physical exam. and drug test
  • High school diploma or GED preferred



This job requires one to lift, carry, push, and/or pull materials and equipment weighing up to 20 pounds as well as the ability to stand, sit, walk, and effectively communicate (oral, written, non-verbal) with others. This job typically requires 85% sitting, 10% walking, and 5% standing and is performed under all weather conditions and temperature throughout the year. This role requires one top ascend and descend stairs and may require the reassignment of bus routes to support the operational needs of the School. Incumbents will be required to work before- and after-school hours, and may occasionally be ask to provide coverage during the school day, evenings, and weekends.

Dexter Southfield’s 36-acre campus is comprised of several buildings, playing fields, and outdoor learning spaces, which are accessible via internal and external walkways, stairs, nature paths, hills, and uneven terrain. This position requires one to transfer between these areas in all weather conditions.

All employees of Dexter Southfield are required to verify employment eligibility and successfully complete CORI, SORI, and fingerprint-based background checks as a condition of employment.

Interested candidates are encouraged to send a cover letter, resume, and completed employment application to Carmen Urbonas, Director of Human Resources, at


Dexter Southfield School • 617-522-5544 •

Report an Absence • Admissions: 617-751-3600

20 Newton Street Brookline, Massachusetts 02445 Directions


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