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Kalana Wijesekara began their work experience in 2008 as a Trainee Software Engineer at Aeturnum. Kalana then worked as a Software Engineer at Aeturnum from July 2010 to February 2011. In 2011, they joined 99x and started as a Software Engineer before progressing to roles such as Senior Software Engineer, Associate Technical Lead, Technical Lead, and Senior Technical Lead. From February 2019 to February 2020, they served as an Associate Technical Architect. Kalana then became a Technical Architect from February 2020 to January 2021. Kalana was promoted to Director of Software Engineering in December 2021 and most recently assumed the role of Chief Developer Experience Officer in March 2023.

Kalana Wijesekara completed their education with a Master's degree in Advanced Software Engineering from the University of Westminster from 2012 to 2014. Prior to that, they earned a B.Sc Hons degree in Software Engineering from the same university, from 2006 to 2010. In addition to their formal education, Kalana also obtained additional certifications, including the Scrum Foundation Certificate from CertiProf in August 2020 and the Certified ScrumMaster® (CSM®) from Scrum Alliance in September 2013. Kalana also completed a course titled "Shaping up with Angular.js" from Code School, although the specific dates of completion are not provided.