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Jesslyn Stanley has a diverse work experience starting from 2016, where they worked as a Furniture Maker. In 2018, they joined GoSpotCheck and held various roles including Weekend Software Support, Tier 1 Support Lead, and Technical Support Analyst until 2021. From 2021, Jesslyn joined Skilljar as a Product Support Specialist and later transitioned into the role of Implementation Manager in 2022.

Jesslyn Stanley attended Georgia Southern University from 2006 to 2009, where they obtained a bachelor's degree in Psychology. Jesslyn also holds certifications including being a Skilljar Certified Professional - Basic from Skilljar, obtained in April 2022, and completing a Moral Reconation Therapy program through the Department of Corrections- NZ, although the specific month and year of completion are not provided.