Bailey Bressler

Bailey Bressler is a seasoned professional with extensive experience in sales, business development, and political consulting. Currently serving as a Senior Provider Growth Associate at Headway, Bailey achieved a notable 127% blended quota attainment in Q1 2025 and previously managed a portfolio of 250 client accounts as a Provider Growth Associate. Prior roles include Outbound Sales Development Representative at Skilljar by Gainsight, Political Compliance Consultant, and various positions within the Washington National Guard, where responsibilities included CBRN defense and tactical operations. Bailey has also contributed as an Enterprise Senior Market Development Representative at DocuSign, along with experience in business development and campaign consulting for various political organizations. Educational credentials include a Bachelor’s Degree in Political Science from Washington State University and studies in Buddhist Studies and Spanish Language.