Robert Leon Wilkie, Jr. was born on August 6, 1962, in Frankfurt, West Germany. He was the son of a US Army artillery commander and grew up at Fort Bragg in Fayetteville, North Carolina. In 1985, Wilkie received his bachelor's degree from Wake Forest University. He then attended Loyola University School of Law, graduating in 1988, followed by a degree in international and comparative law from Georgetown University. In 2002, he received a master’s degree from the United States Army War College.

Wilkie has more than 20 years of federal service, beginning when he was a young aid to Senator Jesse Helms (R-NC). He then worked for Senate Majority Leader Trent Lott (R-Miss) from 1997 to 2003. That year, he joined the George W. Bush administration as a special assistant to National Security Advisor Condoleezza Rice. From 2005 to 2009, Wilkie was the Assistant Secretary of Defense for legislative affairs during Bush’s second term. Wilkie also has extensive military service, having been in both the US Air Force Reserve and the US Navy Reserve.

Wilkie left the government to go to the private sector in 2010. He was vice president for CH2M HILL, a global engineering company that provided construction, design, consulting, and operations services for corporations and governments.

Wilkie rejoined the federal government in 2015, when he became a senior advisor for Senator Thom Tillis (R-NC). In 2017, President Trump nominated Wilkie to serve as Undersecretary of Defense for Personnel and Readiness. After David Shulkin left his position as Secretary of Veterans Affairs, Wilkie was the acting Secretary of the VA until his confirmation by the US Senate on July 23, 2018, a vote of 86 to 9. He was officially sworn in as the 10th Secretary of Veterans Affairs on July 30, 2018.