In September 2008, Showtime announced Hailey would star in The Farm, a "pilot presentation spinoff" of The L Word, to be written and produced by Ilene Chaiken, creator and executive producer of The L Word. It was announced in April 2009 that the show would not be picked up by Showtime.
Hailey has appeared in several Yoplait yogurt commercials as well as a BMW commercial. In April 2008, Hailey was named spokesperson for Olivia Cruises, a travel company which sells cruises and resort vacations marketed towards lesbian customers. She also stars in the psychological thriller Fertile Ground.