The construction industry has yet to reach significant levels of digitalisation compared to other sectors, which could enhance its processes. Recent building failures globally have eroded public trust in the industry, highlighting issues of compliance. This has prompted the introduction of building regulations, where digitalisation is expected to play a key role in supporting compliance. This paper aims to assess the impact of digitalisation on two key stakeholder groups within the construction industry—designers and builders—across various organisational sizes. A questionnaire survey was conducted with designers and builders in Australia, focusing on information technology (IT) infrastructure, digital capability, training, and research and development. Descriptive statistics were analysed and cross-analyses between designers and builders, as well as across different organisation sizes, were conducted using the Mann–Whitney U and Kruskal–Wallis H tests. The findings revealed clear differences between designers and builders regarding digitalisation across IT infrastructure, digital capability, training, and R&D. For example, builders primarily rely on cloud storage while designers use a combination of local and cloud storage. Designers allocate a higher percentage of their turnover to IT, whereas builders are twice as likely as designers to lack structured training for digital skills. When organisation size was considered independently, similarities were observed across sizes. These results provide insight into the current digitalisation landscape in construction, offering a foundation to support the adoption of future industry regulations.