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Michaela Wessels has over 14 years of work experience in the retail and software industries. Michaela began their career in 2006 as a Merchandise Planner for Truworths. In 2010, they moved to Woolworths Limited as a Merchandise Planner. From 2011 to 2012, they worked as a Senior Merchandise Planner for M Webster Holdings (Jigsaw | David Lawrence | Marcs). Michaela then moved to True Alliance as a Merchandise Manager - Fashion Brands from 2012 to 2014. In 2014, they became Director of Merchandise for THE ICONIC. From 2015 to 2018, they worked as a Consultant - Merchandise Buying & Planning for Smart in Planning. Most recently, they have been the CEO and Co-Founder of Style Arcade Software since 2018.

Michaela Wessels completed their Bachelor of Commerce (B.Com.) in Accounting and Finance from Nelson Mandela Metropolitan University between 2002 and 2005.