[3] Sterling joined the Foreign Service in 1990 after working as a liaison to the United Nations for the Mayor of New York City.

Then, Sterling completed two tours as a political officer in Kazakhstan from 1998 to 2001 and Israel from 2001 to 2005.

Next, he served as the Director for Central and Eastern European Affairs on the National Security Council staff from 2006 to 2009.

Posting back overseas, Sterling served as the Deputy Chief of Mission and twice as Chargé d'affaires in Azerbaijan from 2010 to 2013.

Next, he served as Deputy Chief of Mission and twice as Chargé d'affaires in the Netherlands from 2013 to 2016.