Middle School Success Advisor

Position Title: Middle School Success Advisor

Reports To: Director of Middle School Success

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 Summary 

The Middle School Success Advisor will have the primary responsibility of supporting and advising Steppingstone Scholars from 6th to 9th grade through our college and career readiness programming. The Advisor will be a part of a team that helps students develop the skills to successfully navigate middle school, supports their transition to high school, and empowers them to identify and connect their interests to decisions about college and beyond. This multifaceted role blends supporting the academic and social-emotional needs of Scholars through individual advising, as well as through leading, implementing, and contributing to a large number of department-wide events and projects that offer support to larger groups of Scholars and families. During the school year, sessions are held regularly on Saturdays and Wednesday evenings. Occasional events may happen on other weekday evenings as well. The Advisor will work a Tuesday – Saturday schedule during the academic year and a Monday – Friday schedule during the summer. 

Academic Year Schedule:

The Advisor will work a Tuesday-Saturday schedule during the school year. Wednesday afternoons during the school year end around 6:30 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. - 3:00 p.m., with some flexibility around remote work in the afternoon hours. 

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 the end of 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: Early September 2022

Salary: $44,500



  • Develop one-on-one relationships with Scholars and their families in order to support each Scholar’s individual needs 
  • Maintain knowledge of resources and opportunities relevant to Scholars in order to ensure their success in school and in the high school selection process
  • Teach social emotional classes in the summer and academic year
  • 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

Program Implementation

  • Work with team to create and implement curriculum for our college and career readiness programming
  • 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
  • Implement and contribute to the departmental college readiness plan through small group facilitation, workshop development, and the management of other projects 
  • Contribute to the team’s communication and relationship with a group of schools in order to support Scholar success
  • 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
  • Assist with program-wide responsibilities, including the admissions process for incoming applicants, financial aid applications to independent schools, and teaching non-academic classes in the summer 


Required Knowledge and Skills: 

  • Demonstrated commitment to educational and racial equity in college access and success
  • Knowledge of how to support first-generation college-going students on their path to college
  • Experience working with middle-grade and/or high school students, incorporating cross-cultural competency to support and challenge them appropriately
  • Strong verbal and written communication skills  
  • Experience as an effective team member 
  • Strong relationship-building and group facilitation skills across differing stakeholders
  • Effective project management skills with demonstrated initiative, flexibility, and problem-solving capabilities
  • Bachelor’s degree required in a relevant field 
  • Knowledge of Boston public, charter, or independent schools is desirable
  • Preference given to candidates who are bilingual in Spanish, Vietnamese, Arabic, Haitian Creole or Chinese (Mandarin or Cantonese) 
  • Ability to make a minimum two-year commitment required

Physical Demands: 

  • Lifting up to 20 pounds, standing, walking, sitting, reaching, operating computer and office equipment 

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 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