Construction is a complex activity, characterized by high levels of capital investment, relatively long delivery durations, multitudinous risks and uncertainties, as well as requiring the integration of multiple skills delivering a huge volume of tasks and processes. All of these must be coordinated carefully if time, cost, and quality constraints are to be met. At the same time, construction is renowned for performing poorly regarding sustainability metrics. Construction activity generates high volumes of waste, requires vast amounts of resources and materials, while consuming a significant proportion of total energy generated. Digitalization of the construction workplace and construction activities has the potential of improving construction performance both in terms of business results as well as sustainability outcomes. This is because, to put it simply, reduced energy usage, for example, impacts economic and “green” performance, simultaneously. Firms tinkering with digitalization, however, do not always achieve the hoped-for outcomes. The challenge faced is that a digital transition of construction firms must be carried out at a strategic level—requiring a comprehensive change management protocol. What then does a digital strategy entail? This study puts forward an argument for the combined economic and sustainability dividends to be had from digitizing construction firm activities. It outlines the requirements for achieving digitalization. The elements of a comprehensive digitalization strategy are cataloged, while the various approaches to developing a digitalization strategy are discussed. This study offers practitioners a useful framework by which to consider their own firm-level efforts at digitalization transition.