Insurance portfolio management is a slow, sleepy, backward-looking process, and has been for a long time. While the tools have changed a bit, little about the book management process has altered in the last 30 years. The advent of new risks, increased automation, and predictive models has made underwriting an increasingly complex function. Portfolio management needs to evolve to provide management with the insights it needs to manage this complexity. Underwriting organizations need to be able to sense, assess, and respond to the market faster to produce superior underwriting results. This report looks at some of the questions insurers need to ask themselves.