[2] Early in his career, Brady served as an executive editor for The Washington Post (from 1987–1999 and 2004–2009) and AOL (from 1999–2003) before deciding to pursue online news.

[2] Later, at Digital First Media, Brady served as editor-in-chief starting in 2011 and oversaw hundreds of news entities ranging from newspapers to online sites.

[5] Afterward, by the summer of 2014, Brady launched and became the CEO of Stomping Ground, a local online news platform based in Philadelphia, and also taught journalism at Temple University.

[1] At the Knight Foundation, he has overseen the organization's investments in news organizations—specifically black-owned newsrooms, startups based in marginalized communities, and otherwise institutions rooted in diverse perspectives in reporting—with an emphasis on promoting an "effective democracy" and "informed citizenry.

[15] In January 2025, Brady announced a collaborative partnership between the Knight Foundation and the Associated Press in order to "strengthen local news ecosystems at a time when reliable information is harder to find than ever.