Robby is a theatre director, producer, and educator whose work centers on new play development, contemporary theatre, and bold reimaginings of classic texts. His productions have been staged at regional theatres, new play festivals, and universities across the United States.

Directing Robby has directed at Marin Theatre Company, Backyard Renaissance Theatre Company, Tantrum Theatre, UNC School of the Arts, Cygnet Theatre, Charlotte Conservatory Theatre, RhinoLeap Productions, Anacostia Playhouse, and others. His work in new play development includes world premiere productions of plays by Keiko Green, Kate Hamill, Nathan Alan Davis, Cliff Odle, and Paul David Young, with developmental work at the Milwaukee Repertory Theater, Ashland New Play Festival, Eugene O'Neill Theater Center, Woolly Mammoth Theatre, and Playwrights' Center, among others.

He is a two-time recipient of the William R. Kenan Jr. Directing Fellowship at the John F. Kennedy Center - the only artist to have received the fellowship twice - and a 2019 Craig Noel Award winner for Director of the Year. His productions have received 12 Craig Noel Awards in total, including Outstanding Dramatic Production (2025). International fellowships include residencies in Spoleto, Italy; Mareuil-en-Périgord, France; and Valencia, Spain.

Producing As Associate Artistic Director at Cygnet Theatre, Robby produced 49 mainstage productions, led new play development, adult education, and EDI initiatives, and commissioned new works from playwrights including Kate Hamill, Nathan Alan Davis, Herbert Siguenza, Leah Nanako Winkler, and Miranda Rose Hall, among many others. He also produced the National New Play Network's 25th National Showcase of New Plays at Queens Theatre in New York and served as NNPN Producer in Residence at Marin Theatre Company.

Teaching Robby has taught directing, acting, intro to theatre, text analysis, and MFA collaborative courses to designers at UNC School of the Arts, Ohio University, San Diego State University, UC San Diego, and Grossmont College, among others. His teaching integrates professional rehearsal practices and new play development, connecting students directly to working theatre artists.

Robby holds a BFA in Theatre Directing from UNC School of the Arts and has trained with Anne Bogart, Kristin Linklater, Bartlett Sher, Ohad Naharin, and others.