Benjamin's associate directing projects include the Broadway and San Francisco productions of Harry Potter & the Cursed Child, Sing Street at New York Theatre Workshop, The Glass Menagerie starring Cherry Jones both on Broadway and at the Edinburgh International Festival, and the annual national tour of Elf, the musical, among many others. He directed the 50th Anniversary Gala for the New York Library of the Performing Arts honoring Angela Lansbury, Mikhail Baryshnikov, and Jessye Norman. As a producer and director, he has created original live and animated content for Oracle.

A graduate of Muhlenberg College, Benjamin grew up in Pittsburgh and now lives in New York City.