Oakley grew up in rural Minnesota and graduated in 2018 from Gustavus Adolphus College with a degree in religion and political science. Prior to and throughout college, Oakley worked as a political activist with various organizations, such as Students for Liberty, and local campaigns. In the summer of 2017, he interned at a philanthropic firm, Stand Together, where he researched nonprofits around the country. Oakley joined the team at IHS in July 2018 and currently works as a Student Program Specialist. In his free time, Oakley enjoys language learning, reading, traveling, and playing the occasional video game.