Since the beginning of the 21st century, digital transformation has emerged as a key opportunity for work organisations. It promises to integrate back-office and front-office information systems and create new value for organisational products and services. Digital transformation affords many organisations to move beyond the confines of their own structures, systems, and processes and deliver a more personalised experience for their customers. Yet, the implementation of such transformations has not gone well. Studies reveal that over ninety per cent of such initiatives have failed to deliver in their promised benefits, typically reported as underperforming in terms of project scope, over running on scheduled timelines and overspending on expected budgets. A review of the literature reveals the importance attributed to top management in supporting digital transformation success. Yet, there remains a lack of empirical understanding about this topic. This study sought to fill this gap in knowledge by conducting a longitudinal exploratory case study methodology. The study was conducted between 2017 and 2020, deploying case-based methods such as semi-structured interviews with senior and middle managers, on-site visits, and organisational documentation. The case begins in 2016 with the announcement of the digital transformation of the People`s Bank at a projected cost of €500 million. The final cost of the digital transformation was in the region of €1.4 billion. An exploratory case study revealed the complexity associated with such large-scale digital transformations, with four key approaches to top management support identified throughout the project life-cycle; (i) Reimagining,- strategy centric, which explores the fit between business and digital strategy, (ii) Reconfiguring- people-centric, which emphasises buy-in for digital cultural change (iii) Reinventing-customer-centric, which explores digital value creation opportunities (iv) and Recalibrating-operations-centric, where digital capabilities are enabled across the organisation. These approaches are viewed as a holistic suite of managerial actions in support of digital transformation.