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Oskar de Felice's work experience begins in 2007 as a Computer Lab Assistant at Universität Konstanz. In 2010, they become a Student Assistant at Europa Universität Viadrina, a role they hold until 2012. In 2013, Oskar works as a Legal Trainee at the German Foreign Office for a brief period. Oskar then moves on to Linklaters in 2014, where they continue as a Legal Trainee until 2014. In 2015, Oskar joins the German Permanent Representation to the EU as a Legal Trainee for a few months. From there, they move to Flightright in 2015, where they hold various roles, including Research Associate from 2015 to 2016, Legal Counsel Development and Strategy from 2016 to 2019, Head of Legal Product from 2019 to 2022, and currently as the Chief Legal Officer since May 2022.

Oskar de Felice began their education at the Christianeum, where they obtained their Abitur (A-level) degree between 1996 and 2005. In 2006, they enrolled at the University of Konstanz to study law, but it is unclear if they completed a degree at this institution. Oskar then pursued an Erasmus program at the Università degli Studi di Milano-Bicocca in 2009, specializing in Völkerrecht (International Law) for a brief period. Continuing their legal studies, Oskar de Felice attended the European-University Viadrina from 2009 until 2012, earning their 1. State Exam degree in law. Finally, they further advanced their legal training by becoming a legal trainee (Rechtsreferendar) at Kammergericht Berlin from 2012 to 2015, completing their education with a 2. Staatsexamen degree.