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Olesya graduated from Pskov State Pedagogical University n.a. Kirov (teacher of Russian and literature, practical journalism). Later Ms. Shashkova had enhanced training at the DPO Center for Advanced Studies "Russian School of Management" in the field of HR administration. Ms. Shashkova began her career at Bourevestnik, JSC as an engineer in the personnel and training department in 2016. On October 01, 2018, she became deputy head of the department, and from December 1, 2018, she heads the personnel and training department of Bourevestnik Innovation Center.

Since June 1, 2020, she has been acting as Deputy General Director for Human Resources and General Affairs. Since August, 25th – Staff Director.