More than 20 years ago, Oracle executive Mark Benioff believed companies of all sizes, not just large companies, needed an information technology platform to drive their future success. He teamed up with three colleagues and successfully pitched his idea to investors, which included Oracle boss Larry Ellison. The company Salesforce was founded in 1999, offering a Customer Relationship Management (CRM) software system to potential users. The company knew from the start it needed to train both its own and its customers’ workers in the system, and more recently realized it could exploit that training through a new division called Trailhead, launched in 2014. In this article, I will describe how Trailhead is already challenging fundamental assumptions in Human Resource Management. In a future article, I will argue Trailhead is sponsoring a new kind of space, a “career ecosystem,” in which to host participants’ careers.