Cheesbrough started his career at IBM before moving to the BBC's commercial operation, BBC Worldwide. He then spent four years at the BBC as Digital Media Controller. He is widely credited for the driving corporation's digital education portfolio and the transition to digital.[4]
In 2023, he Chief Technology Officer of Fox Corporation, he was responsibile for all the Technology in the company and also focused on the separation of News Corporation into two separate businesses in 2013 and works for Robert Thomson after initially working directly for Murdoch.[8]