The female protagonist of the case needs to make an important decision on whether to ‘stay or go’ in her current role at Kappa University. She had been in the university as a Chief Digital and Information Officer for nearly three years but was not given a strategic status, leaving her out of important decisions; yet she is responsible for the biggest budget of the university. The case raises issues on the strategic importance of digital transformation but also the recognition that female IT leaders may or may not have within their organisation and their influence on decision making linked to digital transformation matters. The explores the role of digital leaders and their relation to senior management; the challenges they face when not given a strategic role and the impact that this may have on the organisation’s experience with digital transformation. Further, the case provides the opportunity to students to compare and contrast different employment arrangements such as contracting and permanent employment. The case can be used on courses on digital transformation, digital strategy and IT leadership.