Designing with data helps the service providers to monitor and gain deeper insights from users. However, there are not many design methods of data-enabled design for most design teams to rely on. This research focuses on the early exploratory phase of the design process. The goal was to find a solution that could assist in contextualizing the big-thin data by using experiencing prototyping approach for exploratory purposes. A design tool, data-contextualizing canvas, was designed and iterated by three studies (including seven sessions with eight participants in total) in this project. It assisted designers to prototyping the simulated user scenario in a structured way. And designers could extract insights and relevant data points by using it. The tool was a representation of the new data-exploration process proposed in the end of this research. The design process of data-value-data described a sequence of creative data exploration for establishing the design hypothesis in early design phase. The data-contextualizing canvas was considered to have benefit in 1.offering a constructive way to explore the data and help in inner communication, 2.proposing a different perspectinve in using the big-thin data as design materials, and 3.raising the awareness of user value.