Upper Elementary & Middle School Advisor

Steppingstone Foundation Inc.•Boston, MA

7d•$55,000 - $60,000•Hybrid

About The Position

At Steppingstone, our mission is to prepare students from under-resourced 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 Overview: The Advisor for the Steppingstone Scholars Program will work collaboratively to support the successful execution of this program. This multifaceted role blends supporting the academic and social-emotional needs of students ranging from either 5th to 6th grade or from 6th to 9th grade depending on the role, with program design and implementation. The Advisor will develop deep knowledge of the Boston educational landscape as well as the resources available to assist students and families in navigating their journey to college. In collaboration with the team, the Advisor will support the delivery of the after-school, Saturday, and summer sessions. As a result, Saturday and evening work is required. Academic Year Schedule: The Advisor will work a Tuesday-Saturday schedule during the school year (September - April). Wednesday afternoons during the school year end around 6:30 p.m., and occasional additional evening work that typically ends around 7:00 p.m is mandatory and is communicated in advance. In person programming occurs at The Curley School in Boston on Saturdays 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 remotely, with some flexibility around work hours. Start times vary based on department and day of the week. Summer Schedule: During the summer (May - August), employees will work a Monday-Friday schedule. Steppingstone hosts a 6-week in-person program for Scholars, which will be held 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, PTOs are granted on a very limited basis from the middle of June through August. 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. Steppingstone offers a translation stipend of $500 annually, to be paid out in our biweekly payroll. The Steppingstone office is accessible by public transit and has very limited parking availability. Program staff support the admission of new students and families to the Steppingstone Scholars Program, including interviewing prospective students and families and reviewing applicant materials. Due to the nature of this work, PTOs are granted on a very limited basis in February and additional in-person work is required. Start Date: Spring 2026 Salary: Assistant level: $55,000; Associate level: $60,000 (Salary commensurate with experience and qualifications)

Requirements

Demonstrated commitment to college access and success
Experience working with a variety of perspectives and experiences
Experience working with upper elementary or middle school students, incorporating cross-cultural competency to support and challenge them appropriately
Experience working with students in a classroom or out-of-school time setting
Experience as an effective team member in a collegial environment
Strong relationship-building and group facilitation skills across differing stakeholders
Effective project management skills with demonstrated initiative, flexibility, and problem-solving capabilities
Strong attention to detail and process management
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.
Bachelor's degree required in a relevant field
1+ year of experience working in an education program or school setting preferred

Nice To Haves

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.
Knowledge of independent schools and/or Boston Public Schools is a plus
Experience using Salesforce is a plus

Responsibilities

Develop one-on-one relationships with Scholars and their families in order to support each Scholar’s individual needs
Collaborate with teachers and program staff 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 academic year
Maintain knowledge of resources and opportunities relevant to Scholars in order to ensure their success in school and in the Middle School and High School selection process
Support students through a right fit school selection process for 6th, 7th, or 9th grade, including but not limited to the independent and/or exam school application process and financial aid application process
Guide families to make informed decisions about educational choices
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
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. This includes entering qualitative and quantitative Scholar and family notes in Salesforce.
Contribute to other cross-team office-wide efforts such as curriculum development, the admission process, and internal task forces and committees
Support the admission of new students and families to the Steppingstone Scholars Program