Tutoring

Volunteers will provide one-on-one tutoring for the Scholars in the Middle School Success department during virtual Wednesday programming (4:30 PM – 6:30 PM) and/or in-person Saturday programming (9 AM – 1 PM). This includes helping Scholars develop the academic skills and habits required to be successful at their schools as well as preparing them for the transition into high school.

Volunteers will also co-lead and facilitate other aspects of Middle School Success programming. This includes, but is not limited to our college readiness workshops, educational activities, social time, and electives. There is also opportunity for volunteers to incorporate their own academic and professional experience into these activities, allowing Scholars to broaden their scope of potential college and career paths.

STRIVE Career Mentoring Program

STRIVE (Scholars Thriving through Relationships, Internships, and Valuable Experiences) is Steppingstone’s near-peer mentoring program for college sophomores and juniors. Through this full academic year program, Scholars are matched with mentors with similar experiences, career industries, and overall interests, and participate in a skills-building curriculum.

Scholars and mentors will meet twice per month from August 2025–June 2026. Mentors will have the option to attend virtual Lunch & Learn Sessions the first week of each month.

Steppingstone is seeking mentors who are committed to the timing of the program as well as our mission. Eligible mentors will be “near-peer” young professionals. 

The Board of Ambassadors

The Board of Ambassadors is a group of committed community members who help expand Steppingstone’s reach through advocacy, fundraising support, and relationship building. This board is non-governing and non-fiduciary, providing visible support and serving as thought partners to advance the organization’s mission. Ambassadors promote Steppingstone within their networks, participate in select events and initiatives each year, make an annual personally meaningful gift (with a suggested $10,000 give/get), and help connect the organization with new donors and partners, as well as opportunities that support Scholars and families. 

The commitment is flexible with a renewable two-year term. 

For more information, please contact Caitlin Kenly, Sr. Director of Leadership Giving & Engagement, at ckenly@steppingstone.org.

The Board of Young Professionals

Are you a young professional in the city of Boston who would like to give your time and talents to support Steppingstone's mission? Consider applying for a position on the Board of Young Professionals (BYP)! Steppingstone’s BYP engages individuals in their 20s and 30s representing a variety of career fields to support our mission. Members of the BYP are committed to advancing the efforts of Steppingstone through volunteering, fundraising, mentoring Scholars, and networking.

The BYP meets monthly during the school year and takes the summer off.

For more information, please email BYP@steppingstone.org.