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Simon Bosley has a strong background in finance and operations management. Simon started their career at Sony New Zealand in 2002, where they served as the General Manager of Finance & Operations until 2010. Simon then joined Sony Australia as the General Manager of Finance for Australia & New Zealand from 2011 to 2012. After this, they moved on to Rakon in 2012, initially as the Interim CFO and then as the Chief Financial Officer from 2013 to 2018. Simon's most recent role is as the Chief Financial Officer at Hirepool, where they have been since November 2018.

Simon Bosley attended The University of Auckland from 1987 to 1991. Simon obtained a Bachelor of Commerce (BCom) degree with a focus on Accounting and Commerce. Prior to their university education, Simon attended Rosmini College, although no specific degree or field of study information is provided for this period.