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Leho Kraav's work experience began in 2002 when they worked as a Forward for TTÜ/A. Le Coq in Estonia. From 2004 to 2006, they held a similar role as a Forward for BC Ramat Hasharon in Israel and Torpan Pojat BC. In 2007, they became a Project Manager for Voipster Estonia until 2009. Starting in 2010, Leho worked as a Beta Tester for Skype until 2012. In 2013, they joined CXL as a Partner and served as the Chief Technology Officer, focusing on building the CXL Institute e-learning platform. Currently, they hold the position of Chief Technology Officer at Wynter since November 2019.

Leho Kraav pursued their higher education in the field of computer science and informatics. Leho first attended Southern Polytechnic State University from 2000 to 2002, earning a Bachelor of Science (BSc) degree in Computer Science. In 1997, they enrolled at TalTech – Tallinn University of Technology, where they obtained another BSc degree in Informatics, which lasted until 2005. Additionally, Leho Kraav attended Kent State University in 1999, completing studies in Computer Science. Finally, they attended Tallinna Reaalkool from 1994 to 1997, although the specific degree and field of study are not provided for this institution. In 2003, Kraav continued their education at TalTech – Tallinn University of Technology, where they pursued a Master of Science (MSc) degree in Informatics, which they completed in 2008.