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Jenna Aiello has a diverse work experience spanning several companies and roles. Jenna started their career in 2007 at Woodman's as an Assistant Retail Manager and Buyer, where they were responsible for employee management, hiring, scheduling, and analyzing market trends for ordering. In 2009, they worked as a Visual Stylist at Nordstrom, managing multiple departments, communicating with department managers, and attending regional conference calls. From 2010 to 2011, they served as an Assistant Store Manager at Aerie, overseeing daily operations, maximizing sales, and maintaining a relationship with the district manager. Jenna's next position was as a Visual Coordinator at Work 'N Gear from 2011 to 2012, where they developed visual blueprints and provided feedback on merchandising strategies. Jenna then became a Brand Manager at Work 'N Gear from 2012 to 2013, collaborating with the CEO and Vice Presidents, and assisting with marketing photo shoots. Jenna's next role was as an eCommerce Marketing Coordinator at Work 'N Gear from 2013 to 2014, where they implemented marketing campaigns, coordinated online marketing programs, and monitored budgets. Their most recent position at Work 'N Gear, starting in 2014, is as a Visual Merchandise Manager, where they create and communicates visual direction, develops plan-o-grams, ensures retail store layouts meet requirements, and provides display and merchandising direction.

Jenna Aiello attended FIDM in 2006 for Retail and Fashion Merchandising. Jenna then transferred to Lasell University from 2007 to 2009, where they earned a BA Of Science in Retail and Fashion Merchandising.