In 1998, Metropolitan Life's first vice president of Interactive Commerce faced a plethora of opportunities, challenges, and decisions in charting MetLife's strategy for e-commerce. He wanted to move quickly into transacting Web-based commerce, but he had to consider executive support, infrastructure requirements, possibly disenfranchising the sales force, fast-moving competitors, and the frenzied rate of technology change. The case covers almost all e-commerce start-up issues, but from the perspective of a large, established bricks and mortar business. (A 19-minute video is available for purchase with this case.)