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Aaron Bailey began their career in 2015 as a SMB Sales Representative at Certify, Inc. Aaron then took on the role of Enterprise Business Development Representative and Business Development Representative at the same company. In 2021, they moved to Emburse where they were a Corporate Account Executive III, automating expense reports, AP invoice, and corporate travel for businesses across North America and Canada. In 2022, they accepted the role of AVP, Account Executive at TravelBank, an all-in-one expense management and business travel platform, powering data-backed financial decisions for more than 15,000 companies.

Aaron Bailey attended Bryant University from 2010 to 2012, where they earned a Bachelor of Business Administration (B.B.A.) in Business Administration and Management, General. Aaron then attended the University of Southern Maine from 2012 to 2014, where they earned a Bachelor of Business Administration (B.B.A.) in Risk Management & Insurance.