IoT adoption is a strategic choice that requires a multi-year commitment to develop the specialistic insurance IoT competencies and the leadership competencies needed to transform the way business is currently being done. Although IoT has not yet been systematically addressed by the large majority of insurers, several early adopters have already concretely demonstrated the potential of using this technology in the insurance sector. These successful player journeys show IoT’s extraordinary potential to generate value for insurers, policyholders, and even the entire society. Insurance IoT is a new way of thinking about the activity of assessing, managing, and transferring risks. This new way of thinking for the insurance business fits with a world that is going to be more and more hyperconnected, a trend that insurers can neither stop or ignore.