Ybarra started his career in tech in 1997, working at software development engineer for Hewlett-Packard. Since June of 2000, Ybarra has been an employee at Microsoft, starting out as a systems engineer for Microsoft Windows. He would later be promoted as the senior director of the OEM division, before moving on to the General Manager of Windows 7 in June 2006, and then the General Manager of Xbox Live in 2009.