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Vasily Chekalkin has a diverse work experience spanning over two decades. Vasily began their career at Yandex in 2000 as a Lead software developer and later became the Head of Communication Software Development department. Vasily then joined CiSRA in 2006 as a Senior software developer, where they designed and implemented an Optimising XQuery Processor for embedded environments. In 2008, they worked at both Parrot VM and Optus, where they contributed as a Developer/GSoC mentor and held various roles such as Senior software developer, Team Lead, and Applications Architect. At Yandex, they returned in 2013 as a Principal Software Engineer and later became a Senior Software Engineer until 2018. Vasily then joined Optus once again in 2016 as the Principal Software Engineer and Architect for the Optus Cloud Core project, where they were responsible for the design and implementation of core parts. Currently, they are working at Neara as a Senior Software Engineer.

Vasily Chekalkin attended Kazan State University from 1993 to 1999, where they obtained a Master's degree in Applied Mathematics and Computer Science.