High School Success Advisor

Steppingstone Foundation

Job Description


High School Success Advisor

Reports To: Director of High School Success


Organization Overview:

Steppingstone 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:

In 2021, Steppingstone implemented its new strategic plan which resulted in the restructure of Scholar Support Services, the division that serves Scholars in middle school, high school, and college and their families after the intensive Academy summer and school year program. High School Success serves approximately 350 Scholars and their families in grades ten through twelve. Over 80% of Scholars will be first generation college students and the majority of them come from low income backgrounds. Nationally, college enrollment has shrunk by more than 5% since 2019. Most notably, enrollment among Black freshmen declined by 6.5%. Boston Public Schools has reported that 47% of its 2020 graduation class intended to enroll in a 4-year college. Given these realities, High School Success seeks to build Scholars' and families' knowledge about college, guide them through the college and financial aid application process, and support their decision to enroll at a right fit school. Additionally, the team nurtures this college-going community by fostering their academic and social-emotional development.


The High School Success Advisor will have the primary responsibility of supporting and advising Steppingstone Scholars from 10th to 12th 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 high school, supports their postsecondary transition, 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. The Advisor will work a Monday-Friday schedule. Some evening and Saturday work is required. The Steppingstone office is hybrid with the expectation that employees will work in the office a minimum of two days per week, with some flexibility around work hours.


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: August 2023

Salary: $47,000




  • Develop one-on-one relationships with Scholars and their families in order to support each Scholar's individual needs
  • Develop and maintain knowledge of resources and opportunities relevant to Scholars in order to ensure their success in school and in the college application process
  • Collaborate with program staff to identify strategies that support Scholars' academic and social growth
  • Offer families resources to support student development

Program Implementation

  • Collaborate with the team to develop and implement curriculum and activities for our college and career readiness programming through small group facilitation, workshop development, and the management of other projects
  • Support the development and execution of program climate/culture, reflected in preventative structures, community and family events, and behavior management systems
  • 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
  • Support the admission of new students and families to the Steppingstone Scholars Program


Required Knowledge and Skills:

  • Demonstrated commitment to educational and racial equity in college access and success
  • Knowledge of and experience supporting college access and persistence needs of historically marginalized populations
  • Effective project management skills combined with initiative, flexibility, and problem-solving capabilities
  • Strong verbal and written communication skills
  • Experience as an effective team member
  • Strong relationship-building and group facilitation capabilities across differing stakeholders
  • 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
  • Pursuant to the ADA, Steppingstone will provide reasonable services and accommodation(s) to employees with qualified disabilities in order to perform the essential functions of their employment, except when doing so would be unduly disruptive and/or result in undue hardship to the organization.



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 la

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