He was judicial clerk for U.S. District Judge Jack M. Gordon in New Orleans, Louisiana and was also an attorney with Houston, Texas-based law firm Margraves, Kennerly & Schueler.

Long (D-LA) between 1982 and 1986, and senior counsel for the United States Senate Committee on Commerce, Science and Transportation from 1987 to 1990.

On February 26, 2014, President Barack Obama announced his intent to nominate Holleyman to be the next Deputy United States Trade Representative.

On June 9, 2015, he joined several other gay diplomats in a statement supporting international trade agreements as a means of enhancing LGBT rights worldwide.

[4] Holleyman has been called up as expert witness on issues affecting the software industry including copyright, trade, and emerging policy concerns resulting from increasing use of the Internet.