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James Sherwood has a diverse work experience spanning different companies. James started their career as a Business Development Manager at Allagree Ltd from July 2009 to May 2013. James then worked at SThree as a Specialist Information Management Recruitment Consultant from May 2013 to September 2014. Following that, they joined Morgan McKinley where they held various roles such as Senior Consultant in Information Management, Business Intelligence & Infrastructure from July 2016 to January 2018, and Senior Consultant in Software Development & Senior Appointments from February 2017 to January 2018. After leaving Morgan McKinley, they worked at Randstad Australia as a Senior Consultant in Information Technology from January 2018 to October 2018. Currently, James is the Head of People & Talent at Freelancer.com, a position they have held since October 2018.

James Sherwood obtained a Certificate IV in Human Resources from the Australian HR Institute in 2019-2020. Additionally, they completed a BA HONS degree in International Marketing Management from Bournemouth University. No specific information was provided regarding their time at St. Georges College.