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Oleg Matsko has had various leadership roles throughout their career. In 2002, they were the Chief Financial Officer at Tennessee Valley Infrastructure Group, Inc. Oleg then became a Senior Associate at FourBridges Capital Advisors in 2005 before moving to Deloitte as a Manager later that same year. In 2006, Matsko joined WorldAPP as their Chief Financial Officer until 2014. From 2014 to 2019, they served as the Chief Executive Officer at FORM.com. Currently, they are the CEO of Divoro, starting from January 2020.

Oleg Matsko has pursued various educational and certification courses. Oleg has completed Executive Education from Harvard Business School. Oleg also holds an MBA degree in Corporate Finance from The University of Tennessee at Chattanooga and a BS degree in Accounting and Finance from Bryan College. Additionally, they also pursued law education from Taras Shevchenko National University of Kyiv. Oleg has earned the title of Certified Public Accountant (CPA) from AICPA. No specific start or end years are mentioned for any of the education programs.