Academy Advisor
Job Type

Position Title: Academy Advisor, Steppingstone Scholars Program

Reports To: Director of the Academy, Steppingstone Scholars Program

Organization Overview:

The Steppingstone Foundation prepares students from marginalized communities to access, navigate, and graduate from college through two initiatives, the Steppingstone Scholars Program and the National Partnership for Educational Access (NPEA). The Steppingstone Scholars Program is a direct-service program in Boston that provides academic, social-emotional, and college-readiness services to students, called Scholars, beginning as early as fifth grade and continuing all the way through college graduation. The Steppingstone Scholars Program consists of five components: Admissions, the Academy, Middle School Success, High School Success, and College Success. NPEA connects the people, practices, and innovations for eliminating barriers to educational access, and college and career success for underserved students.

Position Overview:

The Academy Advisor for the Steppingstone Scholars Program will work collaboratively on a small team to support the successful execution of this program. This multifaceted role blends supporting the academic and social-emotional needs of middle school students with program design and implementation. The Advisor will develop deep knowledge of the Boston educational landscape as well as the resources available to assist students and families in navigating their journey to college. In collaboration with the team, the Advisor will support the delivery of the after-school, Saturday, and summer sessions. As a result, some Saturday and evening work is required.

Academic Year Schedule:

The Advisor will work a Tuesday-Saturday schedule during the school year. Wednesday afternoons during the school year end around 7:00 p.m., and occasional additional evening work is mandatory. In person programming occurs at Boston Latin Academy on Saturdays and the Advisor will be expected to be at that location from 8:00 a.m. - 4:00 p.m. in the fall and 8:00 a.m. - 3:00 p.m. in the spring. 

During the school year, this position will be a hybrid role with two days in office, one day at the program site on Saturdays, and two days remotely, with some flexibility around work hours. 

Summer Schedule:

During the summer, employees will work a Monday-Friday schedule. Steppingstone hosts a 6-week in-person program for Scholars, which will be held at Milton Academy in July and August. The Advisor must be able to work in person at Milton Academy, Monday-Friday from approximately 7:30 a.m. - 3:45 p.m., and until 5:00 p.m. on Wednesdays for faculty meetings. Due to the nature of the summer session, PTOs are granted on a very limited basis from mid-June through August.

A $500 home office set-up stipend will be provided upon hire, followed by quarterly stipends of $50. Laptops are provided to each employee to enhance the hybrid experience.

Start Date: Spring 2022

Salary: $44,500



  • Advise a cohort of 25-30 fifth and/or sixth grade Scholars and their families 
  • Collaborate with teachers and program staff to develop strategies to support students’ academic and social growth using a restorative approach
  • Offer families resources to support student development
  • Teach social emotional classes in the summer and at Saturday sessions

School Placement 

  • Support students through a right fit school selection process for 6th or 7th grade including, but not limited to, the independent and/or exam school application process
  • Guide families to make informed decisions about educational choices 
  • Serve as a liaison to independent schools and facilitate relationship-building between school admission offices and Steppingstone 

Program Implementation

  • Work with team to ensure safe and efficient operation of after-school, Saturday, and summer sessions 
  • Support the development and execution of program climate/culture, reflected in preventative structures and socio-emotional curriculum, community and family events, and behavior management systems
  • Plan and implement family meetings and other large events to disseminate information to and build community among families 

Other projects

  • With the assistance of program leadership, use effective systems to track and analyze student progress and program results, including a database and data-tracking tools
  • Contribute to other cross-team office-wide efforts such as curriculum development, the admission process, and internal task forces and committees

Required Knowledge and Skills:

  • Demonstrated commitment to educational and racial equity in college access and success
  • Experience working with upper elementary or middle school students, incorporating cross-cultural competency to support and challenge them appropriately
  • Experience working with students in a classroom or out-of-school time setting
  • Experience as an effective team member in a collegial environment
  • Strong relationship-building and group facilitation skills across differing stakeholders
  • Effective project management skills with demonstrated initiative, flexibility, and problem-solving capabilities
  • Strong attention to detail and process management
  • Bachelor’s degree
  • Preference given to candidates who are bilingual in Spanish, Vietnamese, Arabic, or Chinese (Mandarin or Cantonese) 
  • Knowledge of independent schools and/or Boston Public Schools is a plus 
  • Ability to make a minimum two-year commitment required

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 learned about this position. Applications will be reviewed on a rolling basis.

COVID-19 Vaccination Requirement

As a condition of employment, all Steppingstone employees, including full-time, part-time, temporary and contract employees, and interns, must be fully vaccinated against COVID-19. To be considered fully vaccinated, individuals must have received two doses of the approved Pfizer/Moderna COVID-19 vaccine or single dose of the Johnson & Johnson COVID-19 vaccine, and remain up to date with all boosters recommended by the CDC prior to the finalization of the hiring process. Finalists will be given details about how to demonstrate receipt of vaccination.

Reasonable accommodations will be considered on a case-by-case basis for exemptions to this requirement in accordance with applicable law. Applicants should be aware that for external-facing roles, particularly those involving close contact with students, accommodations that involve remaining unvaccinated against COVID-19 may not be deemed reasonable. Steppingstone will engage in the interactive accommodation process on an individualized basis in light of each particular role.

Employee Benefits:

  • Generous paid time off (over 8 weeks total, as outlined below)
  • 15 days PTO
  • 2 days Discretionary Time Off
  • 5 wellness days
  • 12.5 holidays
  • 2 weeks paid office closure
  • $500 Home Office Set-up Stipend; plus $50 quarterly
  • Health, Dental and Vision coverage
  • Life, Short-Term and Long-Term disability insurance
  • Retirement Plan
  • Tuition & Professional Development reimbursement
  • Flexible Spending Accounts - Health and Dependent Care
  • Pre-tax Transportation Plan (Transit & Parking)
  • Employee Assistance Program (EAP)
  • Membership to the National Partnership for Educational Access (NPEA)

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 a clear and measurable purpose, using data to drive collective decision-making and challenge assumptions.
  • We create spaces for difficult 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 flourish and reach their full potential.
  • We make time for reflection, 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, age, sex, sexual orientation, national origin, or handicap, as defined by law.

Salary Description