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Simon Wheeldon's work experience began in 1988 as a Manager at Accenture, where they worked until 1993. Simon then became the IT Director at Shamrock Marketing from 1993 to 1997. After that, they worked at BusinessObjects as a Pre-Sales Manager for one year. In 1998, they joined Siebel Systems as a Client Manager in the Financial Services sector until 2006. From 2006 to 2009, they held the position of Director Force.com, EMEA at salesforce.com. Finally, in 2009, Simon became the Co-Founder and Chief Operating Officer at CloudApps.

Simon Wheeldon attended Rossall School from 1979 until 1985. Simon then went on to pursue a Bachelor of Science (BSc) degree in Computer Science at the University of Bristol from 1985 to 1988. In addition to their formal education, Simon obtained a certification in Machine Learning from Coursera in October 2020.