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Iain McCaskill started their work experience in 2011 as a Bar Manager at Motherwell Football Club, where they worked until May 2017. In 2018, they joined Ascensos as a Team Manager and is currently working there. In February 2022, they also started working as a Sales Representative at GAP Ltd.

Iain McCaskill attended Dalziel from 1999 to 2004, where they obtained Standard grades. No specific field of study was mentioned.