Connected devices present new opportunities to advance design through data collection in the wild, similar to the way digital services evolve through analytics. However, it is still unclear how live data transmitted by connected devices informs the design of these products, going beyond performance optimisation to support creative practices. Design can be enriched by data captured by connected devices, from usage logs to environmental sensors, and data about the devices and people around them. Through a series of workshops, this paper contributes industry and academia perspectives on the future of data-driven product design. We highlight HCI challenges, issues and implications, including sensemaking and the generation of design insight. We further challenge current notions of data-driven design and envision ways in which future HCI research can develop ways to work with data in the design process in a connected, rich, human manner.