Job Description

Middle 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.

• In Boston, we provide academic, social-emotional, and college readiness programming from as early as fifth grade and continuing through college graduation through the Steppingstone Scholars Program (SSP).
• Nationally, we connect the people, practices, and innovations essential for eliminating barriers to college and career success, through the National Partnership for Educational Access (NPEA).

Who You Are

The Middle School Success Advisor role is a strong fit for an emerging professional who is passionate about educational access, loves working with middle school 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 role that blends academic and social-emotional support of middle school students with program design and implementation, and will thrive on a small collaborative team that supports the successful delivery of after-school, Saturday, and summer program sessions.

Start Date: Spring 2026

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

Responsibilities:

Advising

• Develop one-on-one relationships with a case load of 50 - 70 Scholars and their families in order to support each Scholar’s individual needs
• Collaborate with teachers and staff at independent schools and Boston public schools to develop strategies to support students’ academic and social growth using a restorative approach
• Offer families resources to support student development
• Teach social-emotional classes in the summer and at Saturday sessions during the academic year

Program Implementation

• Work with team to ensure safe and efficient operation of after-school, Saturday, and summer programming
• Support the development and execution of program climate and culture, reflected in preventative structures and social-emotional curriculum, community and family events, and behavior management systems
• Plan and implement family meetings and other large events to disseminate information to and build community among families

Other projects

• Use effective systems to track and analyze student progress and program results, including a database and data-tracking tools
• Contribute to other cross-team office-wide efforts such as curriculum development, the admission process, advancement, and internal task forces and committees
• In collaboration with Placement, supports 8th grade Scholars in the placement process, which includes hosting test prep courses and workshops for families and scholars.

Required Knowledge and Skills:

• Demonstrated commitment to educational access and success
• Experience working with individuals with different backgrounds, perspectives, and experiences
• Experience working with sixth to ninth grade students, in a classroom or out-of-school time setting, working to support and challenge each student appropriately
• Experience as an effective team member in a changing environment; ability to manage multiple projects and priorities
• Strong relationship-building and group facilitation skills across differing stakeholders; resolves conflicts constructively and respectfully
• Demonstrated initiative, flexibility, and independent problem-solving capabilities
• Clear written and verbal communication style; ability to adapt communication style to different audiences
• Knowledge of independent schools and/or Boston Public Schools is a plus
• 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.
• 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:

• Bachelor's degree required in a relevant field
• 1+ year of experience working in an education program or school setting preferred
• Experience using Salesforce is a plus

Academic Year Schedule:

The Middle School Success Advisor will work a Tuesday-Saturday schedule during the academic year. Wednesdays during the school year run from approximately 10:30am-6:30pm, and occasional additional evening work is mandatory. In person programming occurs at The Curley School in Boston on Saturdays during the academic year and the Advisor will be expected to be at that location from 8:00 a.m. - 4:00 p.m.

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 remote, 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.

Summer Schedule:

During the summer, employees will work a Monday-Friday schedule. Steppingstone hosts a six-week in-person program for Scholars, which takes place 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, PTO will be granted on a very limited basis from the end of June through mid-August.

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.

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 (the weeks before Labor Day and New Year’s Day)
• $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

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.