The topic of digital transformation has become increasingly prevalent in recent decades. Its importance is justified by the fact that not only can it change the way companies operate, but also bring to light new business strategies. Indeed, companies have ramped up operational data collection opportunities and adopted digital practices to facilitate new flows of design information, allow teams to interoperate in different ways, or improve system performance. Given that a digital transformation occurs under certain sociotechnical contexts and with specific purposes, their success can critically depend on the ability to unambiguously describe this context and the intended transformation in the form of new operational scenarios. One of the challenges faced when attempting a digital transformation is that these efforts can be ad-hoc and poorly structured, which does not tie the transformation to strategic objectives and operational strengths and limitations. This paper aims at addressing this issue by leveraging an existing systems engineering analysis method called Concept of Operations to provide structure to the digital transformation process. Our work shows that this method has the potential to accelerate the sociotechnical system redesign cycle and generate actionable decisions aligned with strategic goals and operational strengths and limitations.