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Michael Winchester has a diverse work experience in the field of investment strategy and management. Michael started their career at Macquarie Bank in 2000 as a Research Analyst and worked there until 2004. Michael then joined Select Asset Management Australia and held various roles including Research Analyst, Portfolio Manager, and eventually became the Head of Research / Portfolio Manager. In 2013, they joined StatePlus as an Investment Strategist and later became the Acting Chief Investment Officer. In 2017, they moved to Aware Super as the Head of Investment Strategy. In 2019, they joined The Pinnacle Foundation as an Investment Committee Member.

Michael Winchester obtained their Bachelor of International Business degree from Flinders University, which they attended from 1996 to 1999. Michael also spent two years at Chuo University from 1997 to 1998, although no specific degree or field of study is mentioned for this time period. Subsequently, they pursued a Master of Commerce degree in Funds Management at the University of New South Wales, completing their studies from 2001 to 2004.