Freeman's early jobs included working for The Heritage Foundation;[4] Freddie Mac;[5] and the American Association of Health Plans.
[6] From 2004 to 2006, he was a vice president at APCO Worldwide, a global public affairs firm.
[7] In 2006, Freeman became the executive director of a new organization, Discover America Partnership,[8] an advocacy group working to increase the number of foreign visitors to the U.S.[9] In late 2007, that organization, the Travel Industry Association of America (TIA), and the Travel Business Roundtable announced their intent to merge.
[11] Freeman worked at the U.S. Travel Association until 2013[12] In October 2011 he was promoted from senior vice president of public affairs to executive vice-president and chief operating officer.
[6] His wife, Tita Thompson Freeman, was the senior vice president of communications and public affairs at the Business Roundtable.