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Gleb Shestakov's work experience begins in 2013 with an internship at Google, where they analyzed user behavior and ad consumption. In 2014, they worked as an intern at Tailify, helping to prototype the product's UX, and also had a brief internship at TransferWise as a Growth Intern. In 2015, Gleb worked as an Intern at CommerzVentures, analyzing investment themes and companies in the financial technology space. Gleb also worked at Simon-Kucher & Partners as an Associate Consultant, focusing on pricing strategy. Gleb then worked as a Consultant for a brief period before joining Deliveroo as a Senior Analyst, and later as a Performance Analyst for special projects. In 2019, they became an Advisor at 4am Labs. Following that, Gleb worked as the Analytics Lead at Booster until 2023. Currently, they are the Director of Data at Flowspace, overseeing data science, analytics, BI, and data engineering.

Gleb Shestakov earned their Bachelor of Science (BSc) degree in Business Studies from Bayes Business School between 2012 and 2015.