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Leo de Montaignac has a wealth of work experience. From 2006 to 2014, they worked for three different companies. From 2006 to 2010, they worked for Quest, initially as an Account Manager and then as an NHS Account Director. During this time, they were responsible for expanding Windows management sales into commercial accounts in the UK South territory, as well as expanding Quest product sales into the NHS in England and Wales. In 2010, they moved to EMC Computer Systems as a Senior Account Manager, where they managed the relationship between EMC and Universities in London. Finally, from 2012 to 2014, they were the Chief Operating Officer at Weeding Technologies Limited, where they were responsible for leading Weedingtech's growth by implementing their vision and building and supporting their team.

Leo de Montaignac attended Eton College from 1994 to 1999, studying English, Leo'story and Politics. Leo then attended the University of Bristol from 2000 to 2002, where they obtained a degree in Sociology. Leo also holds a TEFL certification from the TEFL Institute.