Position Title: Summer Substitute Teacher

Reports to: Director of Academic Services and Advising

Position Summary:

Steppingstone is hiring substitute teachers for our six-week summer session. The salary for these positions is $7,200 for the full summer.

At Steppingstone, our mission is to prepare students from under-resourced communities to access, navigate and graduate from college. Steppingstone is seeking summer faculty for the Steppingstone Scholars Program, which prepares 5th-7th grade students from public, charter, and parochial schools in Boston to attend middle and high schools that provide a path to college. Once Scholars complete the Steppingstone Scholars Program, Steppingstone supports them in their academic and social development throughout middle and high school, and continues to support them through college to ensure their success and graduation.

Substitute Teachers will:

• attend program everyday to serve as a substitute for anyone who is absent each day
• substitute teach in the following subject areas: Math, ELA, Science, Latin, and Social Studies

Summer Dates:

• Classes: June 29 - August 7 2026; no program Friday July 3, 2026
• Summer Orientation: June 23-25

Responsibilities:

• Participate in faculty orientation (see dates above)
• Commit to be in person at Milton Academy throughout the entire summer session: Classes meet Monday through Friday and faculty hours are 7:45 am - 3:45 pm
• Serve as a substitute teacher for anyone who is absent. Lesson plans will be provided
• Attend weekly afternoon faculty meetings (Wednesdays until 5:00 pm)
• Share certain roles necessary for administering the summer session:
  • leading homeroom
  • co-teaching a weekly elective class
  • supervising study hall and tutoring students
  • monitoring breakfast, lunch, recess, and/or dismissal
• Chaperone field trip to Canobie Lake Park at the end of summer

Required Knowledge and Skills:

• Teaching experience, preferably with middle school students
• An education-related degree, either completed or in progress
• Demonstrates commitment to educational equity and college access
• Demonstrates ability to be flexible and respond appropriately in a fast paced environment
• Excellent cross-cultural sensitivity and experience working with diverse populations
• Strong interpersonal skills and attention to detail
• Excellent computer skills (experience with Google Classroom and Google Apps preferred)

Transportation and Location:

The Steppingstone summer session will be held at Milton Academy in Milton, MA. Faculty members are responsible for arranging their own transportation to Milton Academy. This position does not include housing.

Application Process:

Interested candidates are asked to submit a resume and thoughtful cover letter indicating preference for subject area. Those invited to interview will be asked to deliver a 10-minute sample lesson and will be required to submit a list of three professional references. Interviews will be conducted via Google Meets. Interviews and hiring will be conducted on a rolling basis.

Steppingstone Core Values

• Mission First - Keep Scholars front and center in all we do.
• Lead with Inclusion - Elevate every voice, consider every perspective.
• Stronger Together - Team up and trust each other.
• Own It - Act with integrity, stay accountable, and be transparent.
• Learn. Grow. Innovate. - Embrace change, drive creativity, and never stop learning.

Steppingstone is an equal opportunity employer and will not discriminate against any individual, employee, or application for employment in accordance with law.