After leaving Harvard, O'Keefe spent time consulting news organizations and continuing research before announcing his upcoming book and role as CEO of the Theodore Roosevelt Presidential Library.
It was the first time an online blog story led to major breaking news and O'Keefe's effort became the subject of a Harvard University study: "Big Media Meets the Bloggers: Coverage of Trent Lott's Remarks at Strom Thurmond's Birthday Party.
For both the program and the web, O'Keefe interviewed George Clooney on Darfur,[18] Nora Ephron,[19] Stephen Colbert,[17] Sigourney Weaver,[20] and John Updike.
[22][23] In 2016, O'Keefe took on the role as SVP of Premium Content, overseeing strategy for CNN's Money, Politics, Style, Tech, Travel, Media & Entertainment, Arabic, and HLN divisions.
[24] In 2018, O'Keefe became the SVP of Content Development, overseeing CNN's mobile, social, video, podcast, virtual reality, newsletter, and subscription services.
[26][27][28][29] In January 2019, the Shorenstein Center on Media, Politics and Public Policy, based at the Harvard Kennedy School, announced its Spring 2019 class of fellows, which included people ranging from Adam Serwer, Maria Hinojosa, and O'Keefe.
O'Keefe was Executive Producer of Explore Parts Unknown, winning a Primetime Emmy for Outstanding Short Form Nonfiction or Reality Series, 2018.
O'Keefe was nominated for a News & Documentary Emmy for “Enemy #1: The Hunt for Osama Bin Laden” (2012) and the Joan S. Barone Award for “Congress in Crisis” (2003).