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Ashley Keefer has a diverse work experience across various industries. Beginning in 2010, they worked as an Area Manager at Pappagallo for five years before transitioning to become an Assistant Manager at Overland Sheepskin Co. from 2015 to 2016. In 2016, they then became a Sales Associate at J.McLaughlin for one year. Following this, in 2017, Ashley took on the role of an Apparel Supervisor at Anthropologie for a short period of four months. Ashley then joined Bonobos as a General Manager and held this position until 2020. In the same year, they also started working at BenchMade Modern as a Post Shipment Customer Care Manager. Ashley also has entrepreneurial experience as the Business Owner of Elysian Designs Jewelry since 2013.

From 2017 to 2018, Ashley Keefer attended Career Step to pursue a program in Medical Billing and Coding. The degree obtained during this period is not specified.