[5][6] After college, she worked as a freelance photographer for the Boston Globe, Associated Press, and Getty Images.

In 2005, she worked for David Bohrer, the official photographer for Vice President Dick Cheney.

[4] In 2017, Craighead was named the official White House photographer for Donald Trump.

[4] Craighead photographed Nancy Pelosi standing to address a seated Trump in an October 2019 meeting at the White House, which attracted media attention.

[13][14] She later remarked that Trump liked to "control the lighting, the production, and the show basically", and that he preferred posed over candid photographs.