Interests Section in Cuba, a position he held from September 2011 to July 2014.

[2] Caulfield now works as an independent consultant and an advisor to the Innovadores Foundation.

[3] In September 2008, Caulfield acted as the chargé d'affaires at the American embassy in Venezuela after Ambassador Patrick Duddy was expelled by then-president Hugo Chávez.

Caulfield served in the state department for over 30 years in a variety of posts, including consul general at the American embassy in London and deputy chief of mission at the American embassy in Lima, Peru.

Caulfield is a graduate of Saint Joseph's University with a degree in international relations and Latin American studies.