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Simon Cheadle has a diverse work experience spanning over different industries. Simon started their career in 1996 as the Manager of Australian Schools Rugby at Australian Rugby Union Ltd. Simon then worked as a National Sales Executive at ModusLink from 1998 to 2002. In 2003, Cheadle became the Branch Manager at Entercorp Solutions Pty Limited, and later moved on to join Spark Digital NZ in 2005 as the General Manager of Software Solutions at Gen-i Australia. In 2010, they joined rhipe as the Sales Manager for nSynergy, and in 2012, they became the Chief Executive Officer of Antares Solutions. Most recently, they hold the position of Chief Executive Officer at Argenti since 2018.

Simon Cheadle's education history includes attending the University of Canberra and The King's School, although specific details such as start and end years, degree names, and fields of study are unavailable.