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January Stewart's work experience begins in 2005 at BOC International, Inc. where they worked as an Import Specialist until 2008. January then joined Virgin Pulse, initially as an Office Manager, before progressing to roles such as Human Resources Lead / Staff Accountant, Human Resources Manager, Director of Human Resources, and finally Vice President of People & Culture. In 2018, they joined Tripadvisor as an Associate Director of People Operations Business Partner and gradually worked their way up to Director and then Senior Director of the same role.

January Stewart attended the University of New Hampshire from 2001 to 2005, where they earned a Bachelor's degree in Communication. Prior to that, they also attended Boston Latin Academy. The specific years of attendance and any degrees or field of study obtained from Boston Latin Academy are not provided.