Teaching and Staff Jobs at Hillside School
Hillside School is an independent boys' school in Marlborough, Massachusetts, serving 101–200 students in grades 4 through 9. Marlborough sits in central Massachusetts, roughly 30 miles west of Boston, positioned between the Worcester and Boston metro areas. The school's mixed boarding and day model attracts families across a wide geographic range while offering faculty flexibility in residential arrangement—some teachers live on campus, others commute from surrounding towns.
The academic program emphasizes structure and challenge. Hillside School offers a strong visual and performing arts program, competitive athletics, and instruction in Mandarin Chinese, French, and Spanish taught by specialists who move beyond textbook translation. The Shades of Blue initiative embeds character development into academic life, giving teachers a deliberate framework for mentoring alongside subject instruction rather than treating values formation as isolated from classroom work.
Teaching at Hillside School means wearing multiple roles. Faculty members teach a subject, advise a grade cohort, coach sports, or supervise residential and day activities. For middle school educators, this intersection creates richer student relationships and clearer visibility into growth than traditional compartmentalized structures allow. Adults know individual students across contexts—in math class, on the athletic field, during evening programs.
The school maintains solid financial stability with net assets exceeding $14 million and annual revenue above $10 million, signaling resources for competitive teacher compensation and program support. Hillside School regularly hires for academic faculty in core subjects, arts specialists, coaches, and residential or day staff roles. For educators seeking a small-school environment where individual students remain visible and faculty voice shapes culture, Marlborough's central location and mixed boarding model offer genuine advantages.
*View current openings at Hillside School.*
Open positions at Hillside School
2 current openings. Click any role to apply directly on the school's site.
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