In 2005, Hess joined the writing staff of HBO's Deadwood, writing the second season episode "Advances, None Miraculous".
From 2005 to 2012, Hess wrote 17 episodes of the Fox drama series House. In addition, she served as story editor from 2006 to 2007, executive story editor from 2007 to 2008, and producer from 2008 to 2012.
Since 2013, Hess has written 8 episodes of the Netflix comedy-drama series Orange Is the New Black, for which she is an executive producer.
In 2014, Hess married the musician and actress Talia Osteen.