Description:
Join a mission-driven team supporting and empowering future college graduates!
Who We Are
At Steppingstone, our mission is to prepare students from under-resourced communities to access, navigate, and graduate from college.
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Through the Scholars Program in Boston, we provide academic, social-emotional, and college readiness programming from as early as fifth grade and continuing through college graduation.
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Through the National Partnership for Educational Access (NPEA), we connect the people, practices, and innovations essential for eliminating barriers to college and career success.
Who You Are
The High School Success Advisor role is a strong fit for an emerging professional who is passionate about educational access, loves working with high school age students, and is committed to making a lasting impact on Scholars’ lives. In this role you will develop deep knowledge of the Boston educational landscape and resources available to assist students and families in navigating their journey to college. The ideal candidate will have the skills to excel in a multi-faceted role that 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.
Start Date: August 2026
Salary: $55,000
Responsibilities:
Advising
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Develop meaningful one-on-one relationships with a caseload of Scholars with varied academic profiles and their families in order to support each Scholar’s individual needs, personal growth, and post-secondary success, often referring them to resources and recommending opportunities available to them both in and out of their school settings.
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Advise and maintain ongoing contact through emails, texts, phone calls, and virtual or in-person meetings with a caseload of 100 Advisees in order to ensure a smooth transition and adjustment to their next grade level and to provide guidance and assistance around academic progress, social-emotional well-being, and college and career readiness
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Develop and maintain knowledge of resources and opportunities relevant to Scholars in order to ensure their success in school and in the college application and financial aid processes
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Support grade twelve Scholars and their families through the college, financial aid, and scholarship application process
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Collaborate with program staff to identify strategies that support Scholars’ academic and social growth
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Offer families resources to support student development
Program Implementation
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Collaborate with the team to develop and implement curriculum and activities for our college and career readiness programming for Scholars and their families through small group facilitation, workshop development, and the management of other projects
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Support the development of Scholars’ social emotional learning and foundational skills in a restorative community with high expectations
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Maintain knowledge of resources and opportunities relevant to Scholars to ensure they apply to, persist, and are successful in college
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Contribute to the team’s communication and relationship with a group of schools in order to support Scholar success, including visiting Scholars regularly at their schools
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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. This includes entering qualitative and quantitative Scholar and family notes in Salesforce.
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Prepare for the administration and recruitment of, and participate in the selection of Steppingstone’s annual scholarship program
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Support the admission of new students and families to the Steppingstone Scholars Program
Requirements:
Required Knowledge and Skills:
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Demonstrated commitment to educational access and success
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Experience working with individuals with different backgrounds, perspectives, and experiences
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Experience working with high school students, in a classroom or out-of-school time setting, working to support and challenge each student appropriately
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Orientation towards continuous learning for self and others, particularly within the field of college access and success, and career readiness
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Experience as an effective team member in a changing environment; ability to manage multiple projects and priorities
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Strong relationship-building and group facilitation skills across differing stakeholders; resolves conflicts constructively and respectfully
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Demonstrated initiative, flexibility, and independent problem-solving capabilities
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Clear written and verbal communication style; ability to adapt communication style to different audiences
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Knowledge of independent schools and/or Boston Public Schools is a plus
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Ability to make a minimum two-year commitment required. Two years allow Advisors to fully dive into our work and provide consistency for Scholars and families.
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Preference given to candidates who are bilingual in Spanish, Vietnamese, Arabic, Haitian Creole, or Chinese (Mandarin or Cantonese). Employees may be asked to provide translation services for members of the Steppingstone community and may be eligible to receive a stipend for their assistance.
Education and Work Experience:
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Bachelor’s degree required in a relevant field
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1-2+ years of experience working in college counseling preferred
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Successful experience working with high school and/or college students from varying backgrounds
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Experience in Boston public, charter, or independent schools is desirable
Schedule:
The Advisor will work a Monday-Friday schedule. Weekly evening and occasional Saturday work is required and work schedules can be adjusted accordingly within that week. Evening work typically ends around 7:00 p.m.
This position is a hybrid role with at least two days per week in office 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.
Physical Demands:
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Lifting up to 20 pounds, standing, walking, sitting, reaching, operating computer and office equipment
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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.
Employee Benefits:
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Generous paid time off (over 8 weeks total, as outlined below)
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15 days PTO
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2 days Discretionary Time Off
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5 wellness days
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12.5 holidays
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2 weeks paid office closure (the weeks before Labor Day and New Year’s Day)
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$500 Home Office Set-up Stipend; plus $50 quarterly
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Health, Dental and Vision coverage
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Life, Short-Term and Long-Term disability insurance
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Healthcare Reimbursement Account Plan (HRA)
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Pet Insurance
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Flexible Schedule
- Retirement Plan
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Tuition & Professional Development reimbursement
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Flexible Spending Accounts - Health and Dependent Care
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Pre-tax Transportation Plan (Transit & Parking)
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Employee Assistance Program (EAP)
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Membership to the National Partnership for Educational Access (NPEA)
Steppingstone Core Values
Mission First - Keep Scholars front and center in all we do.
Lead with Inclusion - Elevate every voice, consider every perspective.
Stronger Together - Team up and trust each other.
Own It - Act with integrity, stay accountable, and be transparent.
Learn. Grow. Innovate. - Embrace change, drive creativity, and never stop learning.
A candidate will be found unsuitable for employment with Steppingstone and automatically disqualified if they use threatening language or behavior either written, verbal, or physical during any phase of the interview process.
Steppingstone is an equal opportunity employer and will not discriminate against any individual, employee, or application for employment in accordance with law. Steppingstone will never require lie detector tests or other assessments designed to gauge the honesty of an applicant's responses in accordance with Massachusetts law.
