This article focuses on the changes that the election of Donald Trump enables in education policy domestically and in education discourse internationally. I argue that Trump's own charismatic leadership style is a distraction from the privatisation that it is facilitating through Betsy DeVos, Trump's appointment as US Education Secretary. I draw on two contemporary examples of technology-enabled privatisation in education--cyber charters and predictive analytics using big data--to argue that in the Trumpian era, educational leadership may be shifting from corporatised forms, where professionals understood as "school leaders" fulfil corporate objectives through corporatised means. Instead, Trumpian-era privatised educational leadership retreats fully behind the technology boardroom door, where it renders superfluous lead professionals in education institutions, and where its objectives are to generate profit through re-conceptualising learners as data providers. This analysis highlights the need for new tools and methods to describe and explain what is happening, and to help develop understandings of what educational leadership in this new landscape might be, do or achieve.