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Rosanna Mainassy's work experience includes roles at Steve Madden Europe, Macintosh Fashion Nederland - Invito BV, and WE Fashion. Rosanna started their career as a Junior Buyer at Steve Madden Europe in November 2010 and then went on to become a Junior Brand Manager in November 2011. In November 2012, they became a Brand Manager and was responsible for orders, negotiations, customer relations, and selling results. In February 2014, they joined Macintosh Fashion Nederland - Invito BV as a Buyer for Bags & Accessories. Rosanna then returned to Steve Madden Europe as a Brand Manager and Sales Manager in February 2016 before being promoted to Sales Director in January 2020. Finally, they worked at WE Fashion as an Assistant Buyer from August 2008 to October 2010.

Rosanna Mainassy completed their education at two institutions. From 1998 to 2004, they attended Wessel Gansfort College Groningen, where they pursued an Atheneum program. Later, from 2005 to 2009, they enrolled in the Amsterdam Fashion Institute and earned a degree in Fashion Management, specifically an Ingenieur (Ir.) qualification.