This case presents the second phase of DBS Bank’s internationally acclaimed digital transformation. Upon completing the first phase (2009-2014) of the transformation that radically rewired” the entire enterprise for digital innovation DBS initiated its second digital push in 2015 to address ever-emerging threats from fintech companies and institutional constraints on acquisition-led organic expansion. To DBS the largest bank in Southeast Asia by assets this digital transformation was an on-going journey in building a next-generation enterprise. It centred on developing the core capabilities to be ready for a digital future i.e. the agility to scale technology infrastructure to delight customers to connect with ecosystem partners and to innovate in ways that are unimaginable today. The case details how DBS was preparing these capabilities by undertaking three fundamental “philosophical shifts”: to reinvent DBS by becoming digital to the core embedding DBS in the customer journey and creating a 26 000-person start-up.