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Director of Teaching & Learning
Steppingstone Foundation in Boston, Massachusetts
Date Posted 05/06/2021
Admin-Tutors and Learning Resources
Employment Type Fulltime
Application Deadline Open until filled

Title: Director of Teaching and Learning

Reports to: Vice President of Academic Programs

Position Overview:
The Director of Teaching and Learning will work to ensure the curricular and programmatic success of
the Steppingstone Scholars Program. The Director will oversee curriculum development and program
implementation, train and supervise seasonal faculty members, and support the evaluation of program
results. This position requires strong sta� management skills, along with leadership and strategic
thinking skills, to ensure that the program can meet its ambitious goals.

The Director will work a Tuesday-Saturday schedule during the school year and a Monday-Friday
schedule during the summer months. Wednesday afternoons during the school year end around 7:00
p.m., and occasional additional evening work is mandatory.

This summer, Steppingstone will host an in-person program for Scholars, which will be held at Milton
Academy. The Director must be able to work in person at Milton Academy for the entire summer.
Following the summer session, the Director will work from home for most of the week, with some (yet
to be determined) time in the o�ce. At this point, we do not yet know whether Steppingstone’s
academic year programming with Scholars, beginning this fall, will be remote or in person.

Start Date: Mid-June

Staff Management

  • Serve as direct supervisor of Teaching and Learning Associate
  • Co-facilitate cross-program teams
  • In collaboration with Director of the Academy, co-lead processes around Advisor-Faculty

relationships and collaboration

Faculty Management
Serve as Dean of Faculty
  • Determine sta�ng requirements and lead process of hiring faculty members for summer and
academic year programming
  • Identify training needs and plan and facilitate training opportunities, including faculty
meetings and orientations
  • Complete classroom observations and provide one-on-one feedback
  • Coordinate regular communication with faculty, including weekly email updates

One Appleton Street | Boston, MA 02116 | P 617-423-6300 | F 617-423-6303 |

  • Keep up-to-date with key trends and innovations in pedagogy and instructional technology

Program Management
Lead design and implementation of curriculum for summer and after-school programs, with a

speci�c focus on culturally sustaining curriculum
  • Integrate diversity, equity, and inclusion initiatives into curriculum development, instructional
implementation, and faculty hiring/supervision practices
  • Collect feedback from sta�, faculty, and Scholars to support continuous improvement of
curriculum and program logistics
  • Manage the completion and distribution of student progress reports
  • Teach courses during the summer and academic year sessions as needed

Knowledge Management
Manage the Teaching and Learning department budget, including personnel expenses,

instructional materials, and program events
  • Coordinate the collection of student assessment data and collaborate with Data and Evaluation
Specialist on data analysis in order to tailor curriculum to student needs
  • Enable and ensure optimal use of data and organizational resources to ensure goals are being

met and strategic decisions are implemented

Required Knowledge and Skills
Demonstrated commitment to educational and racial equity in college access and success
  • Experience working with diverse populations
  • Demonstrated knowledge of and experience in culturally sustaining curriculum development
and e�ective instructional strategies
  • Experience integrating technology into the classroom to enhance teaching, learning and
assessment practices
  • Strong sta� management skills and experience successfully managing an e�ective team,
including proven leadership skills and professional judgement
  • E�ective project management skills combined with strong organization and problem-solving
  • Strong relationship-building and group facilitation skills across di�ering stakeholders,
including various internal departments and external partners
  • Ability to utilize qualitative/quantitative analysis and creativity to ensure continuous learning
and program improvement
  • Orientation towards continuous learning for self and others

Education and Work Experience

One Appleton Street | Boston, MA 02116 | P 617-423-6300 | F 617-423-6303 |

  • 5+ years of full-time teaching experience, preferably in grades 5-7
  • 2+ years of management experience
  • A bachelor’s degree is required. An advanced degree in education or a related �eld is preferred.

Salary: $55,000 - $60,000

Physical Demands:
Lifting up to 20 pounds, standing, walking, sitting, reaching, operating computer and o�ce


To Apply:
Please input your resume and a thoughtful cover letter outlining how your skills and experience meet
the quali�cations of the position, and how you learned about this position, by following this link and
selecting “Director of Teaching & Learning.” Applications will be reviewed on a rolling basis.

Steppingstone Core Values
Power of One

  • We honor every voice and believe we are strongest when we work together.
  • We recognize, respect, and nurture the fullness and complexity of each member of
  • our community.
  • We believe in the power of belonging and seek to create a welcoming and inclusive
  • culture.
Walk the Walk
We partner with every Scholar and family, supporting them holistically throughout
  • their own educational journey.
  • We work with clear and measurable purpose, using data to drive collective
  • decision-making and challenge assumptions.
  • We create spaces for di�cult conversations to transform our thinking and move us
  • forward.
Embrace Growth
We strive to operate as an anti-racist organization and commit to continuous learning
  • and action in the service of this goal.
  • We provide opportunities for everyone in our community to �ourish and reach their
  • full potential.
  • We make time for re�ection, learn from past experiences, and take initiative in
  • response to changing needs and new ideas.

One Appleton Street | Boston, MA 02116 | P 617-423-6300 | F 617-423-6303 |

The Steppingstone Foundation is an equal opportunity employer and will not discriminate against any
individual, employee, or application for employment on the basis of race, color, marital status, religion,

age, sex, sexual orientation, national origin, or handicap, as defined by law.

*Please mention to employers when applying for this job*
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