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Middle School Advisor

Organization Overview
The Steppingstone Foundation prepares students from marginalized communities to access, navigate, and graduate from college through two initiatives, the Steppingstone Scholars Program and the National Partnership for Educational Access. 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.

Position Summary 
The Middle School Advisor (MSA) will have the primary responsibility of supporting and advising Steppingstone Scholars from 6th to 9th grade through our college and career readiness programming. The MSA will be a part of a team that helps students develop the skills to successfully navigate middle school, supports their transition to high school, and empowers them to identify and connect their interests to decisions about college and beyond. This multi-faceted role 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. 

The MSA will work a Tuesday-Saturday schedule during the school year and a Monday-Friday schedule during the summer months. Occasional evening work is mandatory. 

This summer, Steppingstone will host a 5-week in-person program for Scholars, which will be held at Milton Academy. The Advisor must be able to work in person at Milton Academy. Following the summer session, the Advisor will work from home for most of the week, with some (yet to be determined) time in the office. The format of Steppingstone’s academic year programming with Scholars is still to be determined. 

Responsibilities: 

Advising
  • Develop one-on-one relationships with Scholars and their families in order to support each Scholar’s individual needs 
  • Maintain knowledge of resources and opportunities relevant to Scholars in order to ensure their success in school and in the high school selection process
  • Teach social emotional classes in the summer and academic year
  • 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

Program Implementation
  • Work with team to create and implement curriculum for our college and career readiness programming
  • Support the development and execution of program climate/culture, reflected in preventative structures and socio-emotional curriculum, community and family events, and behavior management systems
  • Implement and contribute to the departmental college readiness plan through small group facilitation, workshop development, and the management of other projects 
  • 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
  • Assist with program-wide responsibilities, including the admissions process for incoming applicants, financial aid applications to independent schools, and teaching non-academic classes in the summer 

Required Knowledge and Skills: 

  • Demonstrated commitment to educational and racial equity in college access and success
  • Knowledge of how to support first-generation college-going students on their path to college
  • Experience working with middle-grade and/or high school students, incorporating cross-cultural competency to support and challenge them appropriately
  • Fluency in both Spanish and English speaking and writing
  • Strong verbal and written communication skills 
  • Experience as an effective team member 
  • Strong relationship-building and group facilitation skills across differing stakeholders
  • Effective project management skills with demonstrated initiative, flexibility, and problem-solving capabilities
  • Bachelor’s degree required in a relevant field 
  • Knowledge of Boston public, charter, or independent schools is desirable 

Physical Demands: 

  • Lifting up to 20 pounds, standing, walking, sitting, reaching, operating computer and office equipment 

Salary: $40,500

To Apply:

Please input 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, by following this link and selecting “Middle School Advisor.” Applications will be reviewed on a rolling basis. 


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.