Dexter Southfield

Dexter Southfield is an independent day school in Brookline, Massachusetts, enrolling more than 1,000 students from pre-school through grade 12. The school uses a parallel single-sex model, teaching boys and girls in separate programs while sharing one campus. Its motto, "Our Best Today, Better Tomorrow," frames a classical curriculum built around a strong liberal arts core.

Teaching at Dexter Southfield is shaped by that parallel structure. Faculty plan lessons for how boys and girls learn at different stages, then bring students together for shared campus life. Language teachers work across French, Latin, and Spanish, and course sequences tend to stay substantive rather than chase trends. The Brookline location, minutes from downtown Boston by the MBTA Green Line, puts faculty inside one of the country's deepest teaching job markets.

Compensation at established Boston-area day schools generally sits at the upper end of the regional independent school market. Day schools do not include housing, but they trade that for a conventional schedule and the freedom to live where you choose. Dexter Southfield reported net assets near $90 million on roughly $68 million in annual revenue in 2023, which points to a school with resources to invest in faculty salaries, benefits, and professional development.

Hiring spans lower, middle, and upper school teaching roles, world language faculty, athletics and arts staff, and the administrative positions a large campus requires. Most faculty searches open in late winter and spring for the following academic year. Leadership roles appear less often but carry real weight given the school's scale.