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Dilshan Tennakoon began their career in 2008 as an Engineer - Technology at Virtusa. In 2010, they took on the role of Consultant at The Open University of Sri Lanka. In 2011, they became a Software Engineer at Assette.

Dilshan Tennakoon completed a Diploma in Information Technology from the Sri Lanka Institute of Information Technology between 2005 and 2007. Dilshan then went on to study for a B.Sc. in Information Technology at Curtin University from 2005 to 2008. Finally, they obtained a Post Graduate Diploma in Technology Management from Staffordshire University between 2011 and 2012.