In November 2009, Bennett found permanent employment at his local newspaper, the "Colchester Daily Gazette". He joined the Parliamentary Lobby in 2014 and was recruited by the "Daily Express", becoming their online political reporter. He then led the political coverage for the "Daily Mirror"'s website, and became deputy political editor of "HuffPost UK". His first book, "Following Farage", was named one of 2015's Political Books of the Year by "The Guardian" and "The Independent". His second book, "The Brexit Club", was published in 2016 and described the efforts of the Leave campaign in the EU membership referendum. "City A.M." appointed Bennett as their head of politics in September 2018.