After she earned her degrees, Pritzker joined the Pritzker organization encouraged by her cousin Nick Pritzker. In 1987, she founded Classic Residence by Hyatt, later renamed Vi, upscale housing for seniors as an alternative to nursing homes. The project struggled at first, losing $40 million in the first 18 months, but turned around after changes in marketing and management. In 1991, Jay Pritzker, Penny's uncle and head of the Pritzker family businesses, named Penny as the director of the Pritzkers' non-hotel landholdings. With that appointment, Penny created the Pritzker Realty Group, which developed apartment buildings, shopping centers, and the Baldwin Park neighborhood in Orlando, Florida.