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Jessie Appleby has over 18 years of work experience. In 2002, they began working as a Network Analyst, Windows & AIX Systems Admin, and Remedy Admin for IBM. Jessie then worked as a Computer Operator for Unisys in 2001. In 2007, they moved to Penn National Insurance as a Computer Operator. Jessie then worked as a Support Specialist II for Select Medical in 2008. From 2010 to 2018, they worked as a Business Analyst/Software Systems Engineer and Network Technician II for Change Healthcare. During this same time period, they also worked as a Change Coordinator for Apex Systems for client Wells Fargo. In 2018, they began working as a Technical Project Coordinator 4 for Insight Global for client Wells Fargo. Jessie currently works as a Care Coordinator for Forward and as a Technology Business Services Analyst for Insight Global for client Wells Fargo.

Jessie Appleby received their Bachelor's degree in Computer Information Systems from Walden University in 2013. Jessie then went on to pursue a Masters in Information Technology from the University of Phoenix, which they completed in 2020.