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Gregory Bailey has a diverse work experience spanning multiple industries. Gregory started their career in the United States Air Force, where they worked as a Contract Specialist and later as a Senior Contract Manager. In these roles, they were responsible for soliciting, evaluating, negotiating, and awarding contracts. Gregory also administered contracts, analyzed cost or price proposals, and developed acquisition strategies.

Gregory then transitioned to krio skincare, where they served as a Strategy Director.

Prior to that, they worked at Sun Life Financial as a Sales Coordinator, where they coordinated the acquisition workflow process and supported the processing of requests for proposals and applications for insurance.

Before their time at Sun Life Financial, Gregory worked at Abercrombie & Fitch as an Assistant Manager. Gregory participated in the Manager in Training program, where they gained experience in managing a multi-million dollar business.

Overall, Gregory Bailey has a strong background in contract management, strategy, sales coordination, and retail management.

Gregory Bailey completed their high school education at Chelmsford High School from 2002 to 2006. Gregory then attended Bridgton Academy for a year from 2006 to 2007. Following this, Gregory pursued a bachelor's degree in Business Administration at Methodist University, where they studied Sports and Fitness Administration/Management from 2007 to 2011. Recently, they obtained their Master of Business Administration (MBA) degree in Business Administration and Management, General from Southern New Hampshire University, completing their studies from 2015 to 2018.