Raised in West London, Penny Pilkington was surrounded by an eclectic mix of artists, gallerists, and collectors from a young age. In 1953, Pilkington’s parents founded the Piccadilly Gallery on Cork Street in central London which they successfully ran together for more than 50 years. After graduating from the University of Bristol, UK, Pilkington moved to New York in 1981 and met Wendy Olsoff on her first day of work at Theo Waddington Gallery. In 1983, Pilkington co-founded P·P·O·W with Olsoff in the first wave of East Village galleries. Since its inception, the gallery has remained true to its early vision, exhibiting politically and socially conscious contemporary work in all media. In 2012, Pilkington and Olsoff received the Visual AIDS Vanguard Award for the gallery's dedication and support of artists in the LGBTQ community and their ongoing leadership in the fight against censorship. She is a member of ArtTable, the foremost professional organization dedicated to advancing the leadership of women in the visual arts, and previously served on the board of Art in General.  In 2021 the gallery moved to 392 Broadway in Tribeca and subsequently opened a second floor space at 390 Broadway.