The transportation sector is undergoing a profound transformation, utilizing digital technologies to move people and goods more efficiently. Data and analytics play a pivotal role as the core of digital transformation and insights-based decision making, as organizations are realizing the necessity of effectively leveraging their data assets. This paper discusses how advanced data analytics techniques, such as artificial intelligence, and solutions can be harnessed to embrace digital innovation and improve operations and services while respecting the transportation industry’s unique requirements regarding stakeholder engagement, user needs, supply chain, legacy systems, stringent safety and security regulations, and system interoperability. This discussion is built around project examples: a Digital Engineering Information Management solution for managing large and complex road construction programs; natural language processing on traffic incident data; a telematic assessment of fuel consumption and emissions from road traffic; and the predictive maintenance of transportation infrastructure. This paper concludes with the proposal of a systematic framework that encourages best practices, clarity, efficiency, and successful outcomes and value extraction from data analytics projects for the transportation sector.