This series of two cases describes the life and career of Donna Dubinsky, a high ranking female executive and entrepreneur. Throughout her career, Dubinsky has remained on the leading edge of the technology field. In the A case, two exciting options lay ahead of Dubinsky, one from 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 (UVA-OB-0844) 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, building and maintaining business and personal relationships, and developing her personal style throughout her professional career.