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Leonardo De Benedetti's work experience includes various roles in the banking and finance industry. Leonardo began their career at Citibank in 1995 as a Warrants sales executive. Leonardo then joined Unicredit in 1998, where they served as the Head of Sales for Warrants and Equity Derivatives until 2000. From 2001 to 2004, they worked at TradingLab Banca Spa as the Managing Director and Head of Sales. In 2005, they joined Banca Aletti as the Head of Corporate and Institutional Sales. Currently, they are employed at Banca Akros, where they hold the position of Head of Banks and Investment Products since 2018.

From 1983 to 1989, Leonardo De Benedetti attended Università Bocconi, where they studied business administration. No specific degree name was mentioned.