A graduate of Swarthmore College with a bachelor's degree in history he continued his education at Stanford University, earning a master's degree in communications. Siceloff has been a producer for ABC's 20/20 and Primetime Live and a senior broadcast producer for ABC News as well as NBC's NOW, Dateline NBC and Prime Story. During 2001 he joined PBS and in 2004 he became founder and CEO of JumpStart Productions, which currently produces NOW on PBS.

Siceloff has been the recipient of many honors and awards including the Alfred I. duPont-Columbia Award and the Peabody award for his work with ABC News' coverage of the aftermath of the September 11, 2001 attacks. He has also received National News Emmy Awards for ABC News segments on the Millennium celebrations and NBC's "The Terror Connection;" a CINE Eagle Award for ABC's "Guatemala;" and an Imagen Award for ABC's "Latin Beat." He also received the Edward R. Murrow Award, Overseas Press Club for a story on child brides for NOW on PBS and was also awarded a National Business Emmy Award in 2007 and a National News Emmy Award for best news magazine segment in 2004 also for NOW on PBS.