Jon Gray has an impressive career history, primarily known for his notable contributions to HomeAway, an Austin-based vacation rental marketplace. From 2004 to 2017, Jon played a pivotal role in the company’s growth and success. As one of the founding employees, he initially focused on supporting merger and acquisition initiatives, establishing a solid foundation for HomeAway’s expansion.

Throughout his tenure, Jon held various key positions within HomeAway, showcasing his versatility and leadership skills. He led strategic efforts in marketing and business intelligence, providing valuable insights for decision-making. His exceptional performance led to his appointment as chief revenue officer, a position he held until the company’s acquisition by Expedia in 2015. Under Jon’s guidance, HomeAway flourished from a humble startup to a remarkable valuation of $3.9 billion by the time Expedia acquired the company. 

Jon has also made significant contributions in the field of consumer internet companies. He has served on the board of directors for Canada Stays and continues to offer his guidance and expertise as an advisor and board member to select companies in this domain. He currently serves as CEO at RVshare, the world’s largest RV rental marketplace.