Kenny trained in Botany at the University of Glasgow before going on to join Addyman Associates, a practice with extensive expertise in archaeology, building and landscape survey, in 1999. In 2006, Addyman Associates became a division of Simpson & Brown under the new name of Addyman Archaeology.
During his career as an archaeologist, Kenny has been involved in numerous projects including work at Culzean Castle in Ayrshire; 26-31 Charlotte Square in Edinburgh; major surveys at the Cowgate fire site in Edinburgh and Brodick Castle on Arran. He was involved in the execution of a comprehensive analytical survey of the Riding House Range at Bolsover Castle in Derbyshire for English Heritage and a similar project involving Queensberry House in Edinburgh for the Scottish Parliament.
Kenny is the in-house specialist for archaeological recording and digitisation. These have included tower houses such as Craigievar or Castle Fraser, Aberdeenshire for The National Trust of Scotland; rural buildings and farmsteadings such as Lawhead Steading and Brunt Steading in East Lothian. Kenny has also been involved in a number of landscapes assessment projects and surveys, including Newhailes Estate in Musselburgh and the Calder Water wind-farm project, Ayrshire.