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Chathura Jayasinghe has had a varied work experience since 2009. Chathura began their career as a Management Trainee at MAS Holdings in 2009. In 2010, they joined EF English First as a Teacher. From 2012 to 2018, they worked as an English Teacher at Beykent University. In 2018, they joined e-Pharma (Pvt) Limited as the Chief Product Officer. Chathura also worked at Hologo World Inc as the Chief Operating Officer and Chief Growth Officer.

Chathura Jayasinghe completed a Bachelor of Commerce - BCom in International Business from Edith Cowan University between 2003 and 2006. Chathura then went on to obtain an Associate's degree in Fashion/Apparel Design from Istituto di Moda Burgo between 2006 and 2008. In 2010, they received a CELTA in English Language from ITI Istanbul.