Bobby Caballero serves as chief executive officer and head of schools at Elsie Whitlow Stokes Community Freedom Public Charter School in Washington, D.C. Known affectionately as “Mr. Bobby,” he has been part of the Stokes community since 2001. In 2025, he completed a two-year leadership fellowship with Greenhouse E3 and led the development of the school’s new five-year strategic plan, launching July 1, 2025. That same year, he guided a comprehensive rebranding effort, introducing a new logo and the motto, “Leading with Love,” reflecting his commitment to building a culture where every person feels included, loved, and seen.

Over the years, Bobby has served in multiple leadership roles at Stokes, including campus director of the Brookland Campus, director of student support, dean of students, and classroom teacher. He played a key role in expanding the school from approximately 60 students to more than 700 across two campuses. He has cultivated partnerships with the National Park Trust, the French American Chamber of Commerce, the International Baccalaureate Organization, Seminar, FundEd, and the Embassy of Panama. He also founded the Stokes Alumni Network, through which more than 30 alumni have returned to serve the school community, including seven current staff members.

Before entering school leadership, Bobby worked as a youth organizer with the Center for Community Change, training young people, including incarcerated youth, to advocate for themselves and their communities.

Born in Havana, Cuba, and raised in Los Angeles, California, Bobby attended Howard University where he majored in Human Development. He enjoys traveling and spending time outdoors with his wife and two sons.