Wickramasekara was born in Raleigh, North Carolina. He attended the North Carolina School of Science and Mathematics and later entered college at the Massachusetts Institute of Technology (MIT). At MIT he earned a Bachelor's degree in Electrical Engineering and Computer Science.
In 2009, Wickramasekara became a research assistant at Liquidia Technologies Incorporated. He moved to General Catalyst Partners as an intern in 2010. He went on to found the software company Benchling in 2012. It is a company that makes collaborative software for scientists, allowing for them to design and run experiments and analyze and share their results with other scientists.
Wickramasekara has received several awards as a scientist and entrepreneur. He was a Grand Winner of the Siemens Competition in Math, Science, and Technology. In 2016, he was named as one of Forbes' 30 Under 30.