Despite of many technology advances, enterprise application designers are facing with organizational challenges in customizing the application to fit with existing business processes and rules in order to ensure effective coordination of work across the enterprise. Much research has advanced the technical aspect of the enterprise application design and development. However, business implications of the design products are seldom addressed or analyzed structurally. A perfectly performed enterprise application can still put the business of the enterprise deploying it at risk if it does not support sound business logic. This paper proposes building business considerations into the software design by using a business risk as a means for evaluating and monitoring the design of an enterprise application under development. To do this, we present an analytical approach to systematically analyze business risks from characteristics of an early high-level enterprise application design. The paper describes the approach and validates it with an illustration on enterprise application design for online shopping.