Henry is an entrepreneur in the hospitality industry. He co-founded InvitedHome, a Boulder-based hospitality company that appeared on the 2015 Inc. 500 list as the highest-ranking company in the travel and hospitality sector. Prior to InvitedHome, he was a founder of the Oakview Group and a sales and marketing manager at Shanghai Vision. He also served as a Techstars associate and spent two years with Cox Communications. Henry was elected to the board of directors in December 2016 and is the great-grandson of Cox Enterprises founder Governor James M. Cox.