High School Success Advisor

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.

• 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.
• Through the National Partnership for Educational Access (NPEA), we connect the people, practices, and innovations essential for eliminating barriers to college and career success.

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.

Start Date:

August 2026

Salary:
Assistant level: $55,000;
Associate level: $60,000

• Develop meaningful one-on-one relationships with a caseload of Scholars with varied academic profiles and their families.
• Advise and maintain ongoing contact with a caseload of 100 Advisees to ensure a smooth transition and provide guidance on academic progress, social-emotional well-being, and college/career readiness.
• Develop and maintain knowledge of resources relevant to Scholars to ensure success in school and the college application/financial aid processes.
• Support grade twelve Scholars and their families through the college, financial aid, and scholarship application process.
• Collaborate with program staff to identify strategies that support Scholars' academic and social growth.

• Collaborate with the team to develop and implement curriculum and activities for college and career readiness programming.
• Support the development of Scholars' social emotional learning and foundational skills in a restorative community.
• Contribute to the team's communication and relationship with a group of schools, including visiting Scholars regularly.
• Use effective systems to track and analyze student progress, including entering notes in Salesforce.
• Prepare for the administration and recruitment of, and participate in the selection of Steppingstone's annual scholarship program.
• Support the admission of new students and families to the Steppingstone Scholars Program.

• Demonstrated commitment to educational access and success.
• Experience working with individuals with different backgrounds, perspectives, and experiences.
• Experience working with high school students in a classroom or out-of-school time setting.
• Orientation towards continuous learning, particularly within the field of college access and success.
• Experience as an effective team member in a changing environment; ability to manage multiple projects.
• Strong relationship-building and group facilitation skills.
• Demonstrated initiative, flexibility, and independent problem-solving capabilities.
• Clear written and verbal communication style.
• Knowledge of independent schools and/or Boston Public Schools is a plus.
• Ability to make a minimum two-year commitment required.
• Preference given to candidates who are bilingual in Spanish, Vietnamese, Arabic, Haitian Creole, or Chinese (Mandarin or Cantonese).

• Bachelor's degree required in a relevant field.
• 1-2 years of experience working in college counseling preferred.
• Successful experience working with high school and/or college students from varying backgrounds.
• Experience in Boston public, charter, or independent schools is desirable.

The Advisor will work a Monday-Friday schedule. Weekly evening and occasional Saturday work is required. This position is a hybrid role with at least two days per week in office.

• Generous paid time off (over 8 weeks total).
• Health, Dental, and Vision coverage.
• Retirement Plan.
• Tuition & Professional Development reimbursement.
• $500 Home Office Set-up Stipend; plus $50 quarterly.

• 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.