From 2010 to 2014, he served as a senior trial attorney in the Seattle office of the Equal Employment Opportunity Commission.

[4] In 2018, Whitehead served as co-counsel for a disabled car dealership employee after he was fired by Mercedes-Benz of Seattle when he began using a prosthetic voice box to speak.

[8] The Court appointed Whitehead as class counsel for over 10,000 detained persons seeking back wages.

President Biden nominated Whitehead to the seat vacated by Judge Richard A. Jones, who subsequently assumed senior status on September 5, 2022.

[15] On January 3, 2023, his nomination was returned to the President under Rule XXXI, Paragraph 6 of the United States Senate; he was renominated later the same day.