[3] After graduating from LSE, Bradfield worked for Gucci Group and Stella McCartney before moving onto a career in advertising in London.
In 2010, Bradfield left JWT and established his own design studio,[3] Present Plus, with Dutch entrepreneur Nalden.
[7] In 2016, Bradfield relocated from Amsterdam to California to set up WeTransfer's U.S. headquarters in Venice, Los Angeles, closer to the company's core client base.
[8][9] In July 2017, Bradfield, in his capacity as WeTransfer president, offered a $10,000 "gift" "to start something" to any of the 173 employees laid off at SoundCloud.
[10][11] Bradfield is chairman of the University of the Underground and The Supporting Act,[12][13] and a trustee of the Sarabande Foundation.