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Ashley Gaa has a diverse work experience spanning from 2006 to 2015. Ashley started their career as a Trish McEvoy Counter Manager at Von Maur in March 2006, then moved on to become a Prescriptives Counter Manager at Younkers in August 2006. In September 2007, they joined Von Maur again as Laura Mercier Business Manager, where they not only applied makeup on clients and managed a full-time associate but also achieved sales goals and merchandised products.

In 2011, Ashley worked as an Account Executive at Napoleon Perdis Cosmetics from February to September. Around the same time, they also served as a Marketing Director at Mal Pearson Productions from September 2011 to September 2012.

Following that, Ashley worked at Fox 42 KPTM as an Account Executive, starting in September 2012 and ending in March 2013. Subsequently, in October 2010, they started their own business called Ashley's Makeup Artistry, where they worked as the Owner, Makeup Artist, and Freelancer. Their services included on-site airbrush makeup artistry for weddings, commercial shoots, print, special events, and any other occasions. Ashley also maintained a makeup blog on their website.

Lastly, Ashley joined Bozell in January 2015 as a Media Buyer, and their tenure at this company is ongoing.

Ashley Gaa began their education journey in 1999 at the University of Central Missouri, where they pursued a degree in Art Education. Ashley completed their studies at the university in the year 2000. Following this, from 2000 to 2001, they attended Missouri Western State University, focusing on Business as their field of study. Continuing their educational pursuits, Ashley Gaa then enrolled at Metropolitan Community College in 2002, where they engaged in studies related to Business/Commerce, General. Their educational journey at Metropolitan Community College lasted until 2003.