[3][4][5] Leonard graduated magna cum laude with a Bachelor of Arts from Boston University, with a major in economics and a minor in French.

In 2004, Leonard received a Master's of Security and Strategic Studies from the Naval War College, with distinction.

Leonard has served overseas as an economic and consular officer in Yaoundé, Cameroon; Windhoek, Namibia; and Lomé, Togo.

Leonard then served as a political and economic officer in Cape Town, South Africa and thereafter as Deputy Chief of Mission in Paramaribo, Suriname.

[2] Leonard's service in Mali was recognized with the Department's Diplomacy for Human Rights Award in 2013, an honor that annually recognizes a U.S. Chief of Mission who has demonstrated extraordinary commitment to defending human rights and advancing democratic principles in his or her host country.

Leonard was appointed by President Obama as the Representative of the United States of America to the African Union, with the rank and status of Ambassador Extraordinary and Plenipotentiary, on July 5, 2016.