This case describes the life and career of Donna Dubinsky, a high-ranking female executive and entrepreneur. Throughout her career, Dubinsky remained on the leading edge of the technology field. In the A case, two exciting options lay ahead of Dubinsky, one with a leader she knew, respected, and had worked for before, and the other from a new contact with an opportunity to lead a small, unproven startup firm. The B case describes her decision and brings the reader up to venture number three called Numenta. The cases are intended to give management students a broad view of one executive's lifestyle, of how she built and maintained business and personal relationships, and the way she developed her personal style throughout her professional career.