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Anna Obolenskaia started their work experience as a Lawyer in 2010 and continued in this role until 2021. In 2022, they joined Ecwid by Lightspeed as a QA Engineer, where they are currently working.

Anna Obolenskaia attended Saint Petersburg State University from 2006 to 2012, where they obtained a Master of Laws (LLM) degree with a focus on Law. In 2021, they enrolled at Voronezh Institute of High Technologies and completed a professional retraining program in Testing PO (256 hours).