Jenny Fleiss.

Jenny Fleiss is a serial entrepreneur who co-founded Rent the Runway, the fashion rental platform, alongside Jennifer Hyman.

Fleiss played a critical role in building Rent the Runway from a Harvard Business School project into a nationally recognized fashion technology company that pioneered the concept of the shared designer closet. After departing Rent the Runway, Fleiss founded Jetblack, a conversational commerce service within Walmart's incubator Store No. 8, which used text messaging and AI to enable personal shopping experiences. Although Jetblack was eventually shut down, the concept of AI-powered conversational commerce that Fleiss explored has since become one of the most active areas of retail technology innovation. Fleiss is a prominent angel investor and advisor to early-stage companies across fashion, commerce, and consumer technology. Her ability to co-found a category-creating company and then continue innovating at the frontier of retail technology demonstrates the serial entrepreneurial drive and creative vision that the Powered 500 Award celebrates.