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Olesya Leary has a diverse work experience spanning over several years. Olesya started their career in 2001 as a PA to the Board of Directors/Procurement Assistant at Serco Integrated Services. In 2003, they worked as a Paralegal at MoneyGram International. From 2005 to 2006, Olesya served as a Legal Counsel at Alfa Bank Group. Olesya then joined MoneyGram International again in 2007, initially as a Regional Compliance Officer, later transitioning to the role of Legal Counsel until 2014. In 2014, they joined Amazon UK as a Corporate Counsel for a year. Finally, in 2016, Olesya became the Head of Legal and Regulatory Compliance at Logifuture.

Olesya Leary earned a Master of Law degree in International Public Law from the University of Westminster in 2001. Prior to that, they obtained a degree in Law with a specialization in Civil and Employment Law from Taras Shevchenko National University of Kyiv, completing their studies in 2000.

In terms of additional certifications, Olesya Leary obtained an ICA Fellow Membership and a Prof. PG Diploma (GRC) from the International Compliance Association in September 2023. Olesya also obtained a CIPP/e certification from the IAPP - International Association of Privacy Professionals in June 2016 and an ICA Certificate in AML (Anti-Money Laundering) in November 2007.