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Winnie Dai's work experience begins in 2010 as a Team Leader at McDonald's, where they worked until 2013. From 2013 to 2014, they worked as an Educator for after-school-care at Belconnen Community Service. In 2014, they joined Sinotrans & CSC Holdings Co., Ltd. as a Marketing Specialist until 2017. Following that, they worked at Crimson Education as an Account Manager from 2017 to 2019, where they managed student accounts and organized events. From 2019 to 2022, they were a Marketing and Partnerships Officer at Golden Key International Honour Society, where they handled partnerships/sponsorships development and managed social media channels. Currently, they are working as an Account Manager APAC at Student.com, starting in 2022.

Winnie Dai received their Master's degree in marketing and management from The Australian National University from 2013 to 2014. Prior to that, they completed their Bachelor's degree in marketing and finance at The Australian National University from 2009 to 2012. Winnie'seducation history also includes attending Maple Leaf International School from 2006 to 2008, where they obtained a Canadian British Columbia High school Certificate with a focus on STEM subjects.