Teaching Opportunities: Summer Session

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Position Summary

Steppingstone hires middle school teachers in all subjects to teach during our six-week summer session in Milton, just outside of Boston. The salary for these positions is $5100. To learn more about teaching with Steppingstone, watch our videos here.

Steppingstone is seeking summer faculty for the following two programs:

The Steppingstone Academy prepares middle school students from public, charter, and parochial schools in Boston to attend independent and public exam schools where they have been traditionally under-represented.

College Success Academy prepares middle school students from Boston K-8 schools, beginning the summer after fourth grade, for high school and college success through a rigorous after-school and three-summer academic program.

Steppingstone subsequently supports all Scholars in their academic and social development throughout middle and high school, and continues to support them through college to ensure their success and graduation.


The Steppingstone Foundation seeks teachers to join The Steppingstone Academy (TSA) and College Success Academy (CSA) in the following subject areas in grades 5-7:

  • TSA & CSA: ELA, Science, Math, Physical Education*
  • TSA only: Writing, Perspectives (social studies/research), Study Skills/Vocabulary*

*PE and Study Skills are typically added to a teacher’s schedule on top of a core academic subject, and only meet 2-3 times each week. For example, a course load may include 3 sections of Math and one section of PE. Not everyone teaches PE or Study Skills, so please let us know if you have a particular interest in one of these.


  • Participate in faculty orientation at the end of June
  • Commit to entire summer session, early July through mid August (classes meet Monday through Friday, approx. 7:45 a.m. – 3:45 p.m.)
  • Teach engaging lessons to 2-4 sections of approximately 12-15 students; classes typically meet 5 times per week.
  • Attend weekly faculty meetings (3:45 – 5:00 p.m.) and complete periodic written evaluations of students.
  • Share certain roles necessary for administering the summer session: monitoring lunch, recess, and dismissal; supervising homeroom and attendance; and co-teaching a weekly elective class.
  • TSA only: Attend the end-of-summer Commencement ceremony for Scholars in their final summer


Candidates must have teaching experience, a strong background in their subject area, experience differentiating classroom instruction, and an interest in working with diverse populations. Independent school or Boston Public Schools teaching experience is preferred. Graduate students will be considered; undergraduate degree is required for summer teachers; undergraduate students in a teacher-training program may be considered for the academic year. Certification is not required.

Transportation and Location

The Steppingstone summer session will be located at Milton Academy in Milton, MA. Faculty members are responsible for arranging their own transportation to summer session classes. Dependent upon geographic location, however, it may be possible for some teachers to be included on the summer bus routes and ride with the students. This position does not include housing.

Application Process

Interviews and hiring will be conducted on an ongoing basis. Interested candidates are asked to submit via email a cover letter indicating preference for subjects and program (The Steppingstone Academy, College Success Academy, or no preference), resume, and list of three professional references to Human Resources at jobs@tsf.org. Please note that candidates invited to interview will be asked to deliver a 10-minute sample lesson.

The Steppingstone Foundation is an equal opportunity employer and we encourage applicants from diverse backgrounds.