Benjamin was an early supporter of Barack Obama's presidential campaign in 2007. He was a co-founder of “Harlem4Obama” which helped encourage Harlem support for the Senator and hosted a fundraiser for him in 2008. After Obama's election, the infrastructure of “Harlem4Obama” contributed to Benjamin's organization “Young Professionals United for Change (YP4C),” which instituted a mentoring program at Wadleigh School and organized young people. In 2012, Benjamin was an Obama delegate to the Democratic National Convention, and raised money for his reelection.