Gilles began learning to skate in 1994. She teamed up with Timothy McKernan in January 2003 after skating with him earlier on a temporary basis. They began competing on the juvenile level in 2004, winning the bronze medal. In 2005, they became the intermediate dance champions. The duo won the junior pewter medal at the 2007 U.S. Championships and silver the following year at the 2008 U.S. Championships. They announced the end of their partnership on May 22, 2008. The partnership ended due to Gilles having physically outgrown McKernan.