Prior to this, he served in the Pentagon on the Naval Operations Staff's Programming Division from fall 2007 through June 2009.

In 1993, he resigned from active duty to pursue a career as a small business entrepreneur in Charleston, South Carolina, during which time he also achieved a U.S. Coast Guard Merchant Master's license.

He then served as Executive Officer in USS Laboon (DDG-58), one of the three ships of the first Atlantic Fleet Destroyer Sea Swap experiment.

[2] He represented the Navy as a 2008-2009 Fellow in the Massachusetts Institute of Technology Seminar XXI program.

[6] Westbrook, a certified defense financial manager[7] completed a 28-year Navy career as Director of the office of Budget Programming Integration (OPNAV N801), known in Pentagon parlance as "The Bullpen."