Increasing computing power, networking capabilities, rapid developments in information and communication technologies have made digital technologies part of our lives and changed the dynamics in the society and in the business world. (Demirkan, Spohrer, & Welser, 2016; Svahn, Henfridsson, & Yoo, 2009). While presenting numerous opportunities for organizations, digital technologies lowered the threshold in the market for new entrants. Therefore, change has become imperative for large organizations in order to survive. This profound and accelerating transformation of business activities, processes, competencies and models to fully leverage the changes and opportunities brought by digital technologies is called digital transformation (Demirkan, Spohrer, & Welser, 2016). Digital transformation presents a novel and complex challenge for organizations regardless which industry they belong to. It is imperative for all the organizations to embrace the deep-rooted, never ending digital journey for their survival. However, going through this journey is not easy for organizations in highly competitive and rapidly changing business environments. Clearly, it is impossible for companies to respond to all the technological developments happening in the world. But how should the companies choose the right technology and how should they apply it? How can they reap the benefits of these technologies in favor of their organization and customers? On the other hand, brand, is an established concept in the literature. It is acknowledged by the literature that it could be a powerful tool for organizations in selecting, guiding and maintaining strategic directions for organizations (Mosmans & van der Vorst, 1998). However, the role of an organization’s brand in digital transformation is not addressed in the literature. This literature gap formed the foundation of this graduation project and was executed in collaboration with Deloitte Digital, a creative digital consultancy which helps large organizations in their digital transformation journeys and striving for acquiring new capabilities and ways of thinking. Exploration of the brand identity of the large organizations in digital transformation and bridging the insights to Deloitte Digital context provided them a new perspective over the digital transformation projects. In order to be able to enable Deloitte Digital consultants in gaining and applying brand-aware perspective on digital transformation projects, “Digital Ambitions” workshops has designed. This workshop, aims to facilitate the creation of future vision and exploration of the possibilities in different domains of digital transformation. Finally, this study has contributed to the research domains of brand and digital transformation in bridging the gap between those by proposing links between them. Additionally, a new perspective for Deloitte Digital is provided that illustrates a competitive advantage in differentiating their approach towards the clients.