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Director of the Academy
Steppingstone Foundation in Boston, Massachusetts
Date Posted 05/05/2021
Nonprofit-Senior/Executive Management
Employment Type Fulltime
Application Deadline Open until filled

Position Overview:
The Director of the Academy will have primary responsibility for the implementation of programming
within the Steppingstone Scholars Program. The Director, along with cross-departmental managers,
will oversee key areas including program content, program operations, and climate and culture, with
an eye toward increasing program e�ectiveness and sustainability. 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 a 5-week 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. The format of Steppingstone’s academic year
programming with Scholars, is still to be determined.

Start Date: June 2021

Staff Management

  • Supervise and mentor �ve full-time sta�
  • Co-facilitate cross-program teams
  • In collaboration with Director of Teaching and Learning, co-lead processes around

Advisor-Faculty relationships and collaboration

Program Management
Serve as Dean of Students, supporting Advisors, Scholars, and families
  • Manage program community and family events
  • Manage implementation of summer and school-year academic program, including systems for

program operations such as safety, communications, meals, facilities, transportation, and

  • Provide consultation to the Director of Teaching and Learning around the development of
curriculum and schedules, as well as hiring and supporting seasonal faculty
  • Teach courses during the summer and academic year sessions as needed

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

  • Integrate diversity, equity, and inclusion initiatives into the development of preventive
structures, social emotional curriculum, and behavior management systems, in collaboration
with the Director of Social Emotional Learning
  • Identify potential innovations to advance program quality, sustainability, and growth
  • Work closely with Director of Middle School Success and Vice President of Support and
College Services to ensure successful Scholar transitions
  • Strengthen relationships between Steppingstone and partner school faculty, administrators,

and community-based organizations (BPS, BASB, ERB, etc.) to leverage resources that support
program development

Knowledge Management
Manage the Steppingstone Scholars Program budget
  • Track and manage program data around attendance, academics, engagement, and other metrics
  • 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
  • Strong sta� management skills and experience successfully managing an e�ective team,
including proven leadership skills and professional judgement
  • Strong relationship-building and group facilitation skills across di�ering stakeholders,
including various internal departments, external community-based organizations, and BPS
  • E�ective project management with demonstrated �exibility and problem-solving capabilities
  • Ability to utilize qualitative/quantitative analysis and creativity to ensure continuous learning
and program improvement
  • Experience in building a strong student culture
  • E�ective teaching and classroom management skills
  • Fluency in Spanish, Mandarin, Cantonese, Vietnamese, Arabic, or Haitian Creole a plus
Education and Work Experience:
Bachelor’s degree required
  • Successful experience working with upper elementary and/or middle-grade students in an
urban, multicultural setting
  • 2+ years of management experience
  • Experience in Boston Public Schools a plus

Salary: $62,500 - $67,000

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


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

To Apply:
Please input your resume and a thoughtful cover letter outlining how your skills and experience meet
the qualifications of the position, and how you learnedabout this position, by following this link
and selecting “Director of the Academy.” 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.

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,

*Please mention academicjobs.net to employers when applying for this job*
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