Josh Gillespie

Josh Gillespie is an accomplished sales professional with extensive experience in various leadership roles. Currently serving as a Sales Trainer at AlwaysHired Sales Bootcamp, Josh focuses on mentoring first-time applicants in tech and sales. As the Founder of Losing by Design, details are still forthcoming. Previous roles include Enterprise GTM at Glassbox, where Josh contributed to the leading digital experience intelligence platform, and a decade-long tenure at PandaDoc as Enterprise Sales Director and Mid-Market & Enterprise Sales Lead, marking the beginning of the sales team as the first account executive hire. Before these positions, Josh held the title of Head of Sales at Pinchit and worked as an Account Executive at Yelp, Inc. Josh holds a Bachelor of Arts in Philosophy from the University of California, Santa Cruz.