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Ashley Simon has a diverse work experience, beginning in 2015 with a role as a Cashier at Kokopelli Farmer's Market. Ashley then worked as a Lab Assistant at the American Sign Language Department and a Freelance Editor at IN*SOURCE. In 2016, Ashley worked as a Caretaker at Senior Helpers, a Sales Representative at Bankers Life, and a Business Development Assistant at Habitat for Humanity of St. Joe County. In 2017, they began working as an English Second Language Instructor at VIPKid and a Freelance Content Marketing Writer & Strategist with Freelance Marketing and Creative Services. In 2019, Ashley began working as an Independent Contractor as a Sign Language Interpreter. Most recently, in 2021, Ashley began working as a Content Writer at Clever Real Estate.

Ashley Simon has a Bachelor's degree in English Language and Literature from Bethel College - Company, which they obtained between 2012 and 2016. Ashley also holds an Associate's degree in Deaf Studies from the same institution. In 2019, Ashley attended Columbia College Chicago to study American Sign Language. Additionally, they have obtained certifications in Content Marketing, Email Marketing, and SEO from HubSpot Academy.