He started his career as a programmer, rapidly rising to be a Managing Director of the most successful software development company in the region – Nortal (then Webmedia). He is a founder of many innovative start-up companies such as zeroturnaround.com, plumbr.eu etc.
He holds a Master of Science degree in Engineering from Tallinn University of Technology. He also holds a number of honorary titles: he is the European CIO of the Year 2014 (by ICT Spring), was the president of the Estonian Association of Information Technology and Telecommunications (ITL) and was elected as Entrepreneur of the Year in 2011 (by Ernst&Young). In 2016, Computerworld elected him among the Premier 100 Technology Leaders.
Taavi is a board member in many ICT initiatives in Estonia and has been the brainpower behind many Estonian e-government innovative initiatives such as e-residency, data embassy, no-legacy policy, free movement of data etc.