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Director of High School Success

Job Description

Full Job Description


Title: Director of High School Success

Reports to: Vice President of Scholar Support Services

Department and Position Overview:

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.

Steppingstone seeks a candidate who has a vision and desire to lead this recent initiative from concept to measurable success. The Director will lead this division successfully by providing effective staff management, program oversight, and data driven decision making. The Director will serve as part of program leadership and collaborate with other directors to ensure college readiness goals are met and that the Scholar and family experience is consistent across their journey at Steppingstone. The Director 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: March 2023

Salary: $62,500 - $67,000


Staff Management

  • Supervise a staff of three direct reports; co-facilitate cross-program teams
  • Support Advisors in developing their knowledge of how to access available resources, support and guide Scholars, and navigate all partner schools

Program Management

  • Lead the planning and implementation of college readiness curriculum and activities for high school Scholars and families
  • Ensure the development of advising systems that support high-quality services for Scholars and families in collaboration with the team
  • Integrate diversity, equity, and inclusion initiatives into preventative structures and behavior management systems
  • Support the admission of new students and families to the Steppingstone Scholars Program

Knowledge Management

  • Implement systems to track and analyze program progress and outcomes in collaboration with internal departments including Data and Evaluation
  • Strengthen relationships between Steppingstone, schools, and community-based organizations to leverage resources that support Scholars' success
  • Ensure optimal use of organizational resources (staff time, budget, technology, etc.) to achieve programmatic results
  • Contribute to other cross-team office-wide efforts such as internal task forces and committees

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
  • Vision and desire to lead this recent initiative from concept to measurable success
  • Strong staff management skills and experience successfully leading an effective team
  • Effective project management skills combined with strategic thinking, flexibility, and problem-solving capabilities
  • Strong verbal and written communication skills
  • Strong relationship-building and group facilitation capabilities across differing stakeholders
  • Orientation towards continuous learning for self and others
  • Preference given to candidates who are bilingual in Spanish, Vietnamese, Arabic, or Mandarin or Cantonese

Education and Work Experience:

  • Bachelor's degree required in a relevant field
  • Successful experience working with high school and/or college students in an urban, multicultural setting
  • Experience in Boston public, charter, or independent schools is desirable

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 submit 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
  • Healthcare Reimbursement Account Plan (HRA)
  • Pet Insurance
  • Flexible Schedule
  • 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.

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