Our speakers include:
JESSICA DESCARTE is the Director of Student Services at Tech Boston Academy, Boston Public Schools. A 2018 graduate of UMass Boston’s Masters in School Counseling Program, Jessica began her career at Tech Boston, a grade 7-12 school, where she started as the school counselor for students in Sheltered English Immersion (SEI) and Students with Limited/Interrupted Formal Education (SLIFE). Jessica also served as a co-content facilitator for the school counseling team, leading the development of the scope & sequence for the school counseling curriculum and facilitating the MyCAP (My Career and Academic Plan) implementation at TBA. In her current role, Jessica oversees student support services at TBA, is the 12th Grade Lead Administrator and she is also a trained bullying specialist. Jessica is the proud daughter of 1st generation Haitian immigrants, which has shaped who she is and how she supports her students and staff. Her school counseling philosophy revolves around building authentic, trusting relationships that foster positive development and encourage lifelong learning throughout a student’s academic career and personal growth. She firmly believes that in order to build these relationships, one must believe that all students, regardless of differences and background, have the right to learn and need to be welcomed in a safe and trusting learning environment. For her work, Jessica was named the 2021 MASCA [Massachusetts School Counselors Association] School Counselor of the Year and currently serves at the Board Chair for the MASCA governing board.
​
DR. OSCAR SANTOS, Executive Director, leads the Center for Collaborative Education’s program and strategic development, operations activities, district leader and superintendent communications, and the organization’s learning and culture. A passion for social change drives Oscar’s work within the organization to help schools and districts embrace educational equity and transformation through entrepreneurship and innovation.
​
Before joining CCE, Oscar was President for Cathedral High School in Boston, where he led a 15,000 square foot expansion to house the Cathedral STEAM Applied Learning Center. During his tenure, the school had six years of 100% graduation and college acceptance. Oscar has also served as the Superintendent of Randolph Public Schools, where he launched an in-district alternative education program, as well as an innovative social emotional learning initiative for all K-5 schools. He was also the principal of Boston International High School, the first school in Boston specifically designed to educate English Language Learners. Prior to going into educational leadership, Oscar served as an AmeriCorps service learning fellow and a high school teacher, where he was recognized as Boston Teacher of The Year. Oscar earned a B.A. and an Ed.D. in Educational Leadership from Boston College. He also earned a Master of Education and a Master of Linguistics from the University of Massachusetts, Boston.
​
CHRIS SMITH, President & Executive Director of Boston After School & Beyond, has led and scaled education, youth development, and college and workforce strategies at the city, state, and national levels. At Boston Beyond, he mobilized a data-driven network of nearly 500 programs reaching more than 20,000 students each year. He spearheaded the nationally-recognized 5th Quarter of Learning with the Boston Public Schools to integrate academics, enrichment, and skill development, an approach which research shows closes opportunity and achievement gaps. He served on the National Academy of Science, Engineering and Medicine committee on summertime experiences. Chris previously worked at the Boston Private Industry Council, where he led Boston’s first comprehensive study of the college completion rates of its high school graduates, and at the US Department of Education in Washington, DC. He earned an MBA from Babson College and a BA from Trinity College.
​
ALAIN MATHIEU is a Partner in the Business Litigation Practice at Prince Lobel, Co-Chair of the firm’s Sports & Entertainment Group, and the current Vice Chair of Crossroads’ Board of Trustees. His legal practice encompasses a wide range of litigation and transactional matters, including complex commercial disputes, trademark and copyright litigation, internal and government investigations, and the negotiation of endorsement/NIL, television and film, licensing, broadcast and streaming, and sponsorship agreements. In addition, he maintains an active pro bono practice in which he represents victims of domestic and sexual violence, asylum seekers, and nonprofit organizations.
Alain has served on Crossroads’ Board of Trustees since 2019. He also serves on the boards of The Wily Network and VISIONS Inc., as well as the advisory boards of the Concussion Legacy Foundation, the Foundation to Be Named Later, and Harlem Lacrosse Boston. Alain is a passionate advocate for the advancement and progress of individuals from underrepresented and underserved communities, as well as safety in youth, amateur, and professional sports.
Alain’s legal and community work has been recognized by various organizations including the Greater Boston Chamber of Commerce, City Awake, the Massachusetts Supreme Judicial Court Standing Committee on Pro Bono Legal Services, Diverse Representation, the National Black Lawyers 40 Under 40, Chambers, Best Lawyers in America, and Super Lawyers.
​
​