Kiley was one of eight women selected to take part in American Film Institute's prestigious Directing Workshop for Women and it was through her participation in this program that she made Some Boys Don't Leave. The film stars Jesse Eisenberg and Eloise Mumford. Kiley received the Student Visionary Award at the Tribeca Film Festival and the Alexis Award for Best Emerging Student Filmmaker at Palm Springs International Shortfest for the film. In November 2014 it was announced that Kiley was included as one of the 20 accomplished female filmmakers chosen to participate in the Fox Global Directors Initiative, a new multi-year program by the studio to develop the talents and networking pools of promising women Directors.

Kiley most recently directed her second feature, Dial a Prayer, from a script she wrote. The film stars Brittany Snow, william H Macy and Glenne Headly and was acquired by Vertical Entertainment for a Spring 2015 release. She is currently in post on a third feature, thriller titled Caught with independent Producer Jennifer Westin and Mar Vista Entertainment. Caught stars Anna Camp as a desperate housewife who abducts the mistress (Stefanie Scott) of her cheating husband and all goes south. Kiley's first feature, Brightest Star premiered at the Austin Film Festival and was released via Warner Brothers and Gravitas in early 2014. Brightest Star was made through the support of the Panavision New Filmmaker Grant and was inspired by the award-winning short film Some Boys Don't Leave. Cast includes Chris Lowell, Rose McIver, Allison Janney, Clark Gregg and Jessica Szohr.