While at Duke, he lived in Estonia during its first year of regained independence, interned for US Senator Ernest Hollings of South Carolina, and worked for the Unaccompanied Children in Exile Project in Croatia.

After graduation, Wilson was selected as a Presidential Management Fellow and assigned to the State Department’s NATO office, working for Ron Asmus, under the tenure of Secretary Madeleine Albright; his fellowship included tours on the China desk and to the U.S. Embassy in Beijing from 1998 to 2001.

He is an advocate for strengthening democratic alliances to address security challenges, believing “US interests are best served when Washington and its allies act in unison.”[16] Wilson views authoritarian Russia and China as “the main geopolitical challenge of the 21st century,” and that “there is no possible successful strategy to confront Putin’s aggression without a strong NATO.”[17][18] From July 2001 to January 2004, Wilson served as deputy director of the Office of the NATO Secretary General, assisting Lord Robertson to transform the Alliance by enlarging NATO membership, implementing the International Security Assistance Force in Afghanistan, and adapting Allied capabilities to face modern threats.

[20][21] From January 2004 to November 2006, as Director for Central, Eastern and Northern European Affairs at the National Security Council, Wilson coordinated U.S. interagency policy on Ukraine during the Orange Revolution, directed efforts to deepen engagement in Central and Eastern Europe, including the expansion of secure visa-free travel, and promoted close consultation with coalition partners in Iraq and Afghanistan.

From December 2007 to January 2009, as Senior Director for European Affairs at the National Security Council, Wilson led U.S. government efforts to advance a Europe whole, free and at peace.

[42][43] In December 2021, alongside USAID Administrator Samantha Power, Wilson moderated a session on human rights and press freedom during the Summit for Democracy.

[44][45] Wilson has been decorated by the presidents and governments of Bulgaria, Estonia, Georgia, Hungary, Latvia, Moldova, and the Slovak Republic for his efforts to advance transatlantic relations.

[50] Wilson currently serves on the board of the Truman Center for National Policy,[51] is a Trustee of the Belarus Free Theatre,[52] and is a member of the Ohrid Group[53] and the International Advisory Council at GLOBSEC.