The insurance industry plays a crucial role of the national financial system, and the operating efficiency of insurance companies has always been a significant subject of academic research. This study proposes a multiperiod DEA model to dynamically evaluate the operating efficiency of insurance companies, which not only overcomes the defect of the traditional DEA method ignoring the internal structure of decision-making units, but also extends the limitation of the leader–follower model in evaluating single-period efficiency. By analyzing the efficiency of seven listed insurance companies in China from 2009 to 2018, the following conclusions are drawn. The multiperiod DEA model demonstrates advantages over the leader–follower model. The profitability of insurance companies during the first five years is higher compared with the last five years. There is a significant correlation between premium financing efficiency and overall efficiency. Throughout both periods, the loss ratio, loss reserve ratio, and consumer price index (CPI) are always positively correlated with the efficiency of the insurer, while the gearing ratio is negatively related to the efficiency of the insurer. The correlation among gross domestic product (GDP), total insurance value, tradable financial assets, and corporate efficiency varies over time.