Digital transformation of financial businesses has been one of the hottest topics for strategic discussions within the industry for several years now. However, these conversations rarely touch upon how decision-making models of underlying technology contribute to the eventual customer experiences. Therefore, while optimising the resources required to digitalise a financial journey, it could be tempting to select a tool with a very simple model at heart. Here, we examine how analytical tools' underlying model quality and granularity can affect the user experience and even the navigation through an institution's strategic roadmap.