After working briefly as a Wall Street lawyer, Cribb served as Assistant to the President for Domestic Affairs in the Reagan Administration, serving as President Reagan’s top advisor on domestic matters. Earlier in the administration he held the position of Counselor to the Attorney General.

He was President of the Intercollegiate Studies Institute from 1989-2011, and served on its board until May 2012. During his tenure, ISI expanded its educational programs. He also served as vice chairman of the Fulbright Foreign Scholarship Board from 1989 to 1992. He was also president of the Collegiate Network, an association of alternative college newspapers; president of the Council for National Policy, a conservative umbrella organization; member of the Board of Advisors for the Foundation for Individual Rights in Education; is counselor to the Federalist Society for Law and Public Policy, a conservative legal organization. Cribb also serves on the Board of Advisors of the Russell Kirk Center for Cultural Renewal, an educational organization that continues the intellectual legacy of noted conservative icon Russell Kirk, and on the Board of Visitors of Ralston College, a start-up liberal arts college in Savannah. He also served as President of the Philadelphia Society.

Cribb has been published in National Review, The American Spectator, The Intercollegiate Review, Modern Age, and Human Events.