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Diana Cholakova has extensive work experience in various finance-related roles. Diana began their career as a Financial Controller at Superior Wholesale Products / Banler Wholesale, Inc in 2004 and later worked as a Senior Financial Analyst at International Meal Company from 2008 to 2010. Diana then joined Navaero as a Finance Director from 2010 to 2012. Diana's career progressed at MasterCard, where they held the positions of Manager, Finance from 2013 to 2014 and Senior Manager, Marketing Finance and Planning from 2014 to 2017. Diana continued to advance in their career at GrandVision NV, serving as Director, Financial Planning and Analysis in 2017 and then as Senior Director, Financial Planning and Analysis from 2018 to 2019. From 2019 to 2022, Diana worked at Honeywell, first as Vice President of Finance, Fiplex Communications, and subsequently as Chief Financial Officer, Fiplex Communications. Currently, they hold the role of Global CFO at Alchemy Global Solutions from 2022 onwards.

Diana Cholakova has a diverse educational background that spans several institutions and fields of study. Diana began their academic journey at Crawford College, though the specific dates and degree obtained are unknown. Following this, Diana attended John Cabot University from 1998 to 2001, where they focused on Business Administration. Diana then transferred to Florida International University, where they completed their Bachelor of Arts degree in Business Administration and Finance in 2002. Diana continued their studies at Florida International University and obtained a Master of Science in Finance in 2005. In addition to their formal education, Diana successfully passed the CFA (Chartered Financial Analyst) level 1 exam through the CFAI (dates unspecified).