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Caleb Gregory has worked in various roles since 2009. In 2009, they worked as a Consultant for Safe Haven Family Shelter. From 2011 to 2012, they worked as a Customer Service Representative for Whole Foods Market and a Consultant for Open Table, Inc. In 2014, they worked as an Apprentice Woodworker for Littlebranch Farm. In 2015, they worked as a Junior Web Developer for Work Institute and an Apprentice Developer for Nashville Software School. From 2016 to 2020, they worked as a Web Developer for Satchel Health and a Mid-Level Full Stack Software Engineer, Software Engineering Manager, and Senior Full Stack Software Engineer for XOi Technologies. Caleb's roles included feature design and development, managing other software engineers, building a development framework for Typescript packages and applications, and acting as a team lead for the core application platform.

Caleb Gregory attended Belmont University from 2008 to 2012, where they earned a Bachelor of Science (B.S.) in Mathematics.