With the development of Chinese medical insurance industry, the amount of claim cases is growing rapidly. Ultimately, more claims necessarily indicate that the insurance company has to spend much time assessing claims and decides how much compensation the claimant should receive, which is a highly professional process that involves many complex operations. Therefore, the insurance assessor’s role is essential. However, for the junior assessor often lacking in practical experience, it is not easy to quickly handle such an online procedure. In order to alleviate assessors’ cognitive workload, we propose an Intelligent Insurance Assessment System (IIAS) that helps effectively collect claimant information through online realtime conversation analysis. With the assistance of IIAS, the average time cost of the insurance assessment procedure is reduced from 55 minutes to 35 minutes.