The paper addresses the topic of digital innovation in the insurance field and the challenges it poses for both companies and regulators. The paper starts with showing how data-driven technologies represent a priceless resource for insurers, allowing new and revolutionary methods to classify policyholders in different merit categories according to risk. The paper then turns to the analysis of new tools at the centre of the recent technological development (i.e. Blockchain and smart contracts) and focuses on the role of Big Data in the insurance sector. The paper thus concludes with some considerations on why access to more types of personal data should be allowed to insurers by regulators, presenting potential advantages not only for the companies themselves, but also for customers and the financial system in general.