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Jessica Ann Fenyin has held a variety of roles in the beauty and retail industry since 2010. Jessica Ann began their career as an Intern at Markowitz Communications in 2010. In 2011, they joined Macy's as an Estee Lauder Account Coordinator, where they actively participated in strategic planning and development for the Philadelphia district. Jessica Ann was also responsible for recruiting, coaching, and developing Counter Managers and Beauty Advisors. In 2016, they took on a Seasonal Educator role at lululemon. In 2017, they joined The Estée Lauder Companies Inc. as a Sales and Education Executive. In 2018, they worked at Shiseido as an Executive Sales and Education Manager for bareMinerals & Buxom and a Retail Territory Manager for bareMinerals and BUXOM. In 2019, they became an Account Executive at Drybar. Most recently, in 2021, they began working as a Regional Sales, Artistry and Education Executive at ILIA Beauty.

Jessica Ann Fenyin's education history includes a Bachelor of Science in Public Relations from Slippery Rock University, obtained between 2007 and 2011, and a high school diploma from Schenley High School, obtained between 2003 and 2007.