Jenny Fleiss

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Co-Founder, Jetblack & Rent the Runway; Venture Partner, Volition Capital

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Jenny Fleiss: Biography at a Glance

  • Jenny Fleiss is the Co-Founder and Board Member of Rent the Runway, an 11 million-member startup that pioneered dynamic ownership in the fashion industry by enabling women to rent designer clothing. 
  • In 2021, Rent the Runway, one of only 20 female-led "unicorn" companies in the U.S. to achieve a $1B valuation, went public.
  • She is a Venture Partner at Volition Capital, a board member of Shutterfly and Party City, and serves as an adviser to and investor in various businesses, many with female founders. 
  • Co-Founder of Jetblack, the first start-up in Walmart's tech incubator, which reshaped the way consumers shop through one-to-one, highly personalized experiences.
  • Named one of Inc. Magazine's "30 Under 30," Fortune Magazine's "40 Under 40" and "Most Powerful Women Entrepreneurs" and Fast Company's "Most Influential Women in Technology."
  • Jenny uses her career experience to speak to business trends as well as entrepreneurship, Intrapreneurship, and Machine Learning

Videos

Biography

Jenny Fleiss is an entrepreneur and intrapreneur, founding two scaled digitally native businesses from scratch: Rent the Runway and Jetblack. She is a Venture Partner at Volition Capital.

Jetblack was the first portfolio company within Walmart’s technology incubator, disrupting traditional e-commerce with a personal shopping service over text message and voice. Previously, Jenny co-founded Rent the Runway, a business that has transformed the retail industry by making designer clothing rentals a convenient and accessible luxury experience for millions of women. During her time at Rent the Runway, Jenny wore many different hats, serving as President, Head of Logistics, and Head of Business Development. Jenny remains a Rent the Runway board member and adviser, is a board member of Shutterfly and Party City, and serves as an adviser to and investor in various businesses, many with female founders. She is the Co-founder of the RTR Foundation and a guest lecturer at various universities and professional forums.

Jenny has been honored with numerous recognitions including Inc. Magazine’s “30 Under 30”; Fortune Magazine’s “40 Under 40” and “Most Powerful Women Entrepreneurs”; and Fast Company’s “Most Influential Women in Technology.”

She earned her MBA from Harvard Business School and graduated Cum Laude from Yale University. She currently resides in New York City with her husband and three children.

Topics

The Power of Data - Insights from Rent the Runway and Jetblackarrow-down

Data has been at the core of building both Rent the Runway and Jetblack. In this talk, Jenny reveals her playbook that businesses of all sizes can apply to ignite their growth.

At Rent the Runway, building an analytics team out of the gate was critical to their explosive success. It opened an ecosystem of intellectual property, from inventory selection to optimal garment cleaning methods. Deep data built for AI powered Jetblack’s conversational commerce platform, enabling Jenny's team to understand key product considerations and consumer attributes, while optimizing one-to-one personalized product recommendations.

But quantitative data is just one part of the equation. The voice of the customer has become even more important amidst the increasingly formulaic and technical landscape. Jenny shows how to effectively inject qualitative data throughout the lifecycle of a company to illuminate unmet consumer needs, innovative behaviors, and fresh business opportunities. For Rent the Runway, this inspired tangible examples like real consumer photo reviews, retail stores, and a massive new revenue stream through subscriptions.

From surveys and focus groups - which can be done at the earliest stages of a company with little resources - to cohort and pricing analyses for conversion optimization, Jenny delivers an actionable plan that will empower audience members to truly understand what drives the growth and profitability of their businesses.

Entrepreneurship – The Story of Rent the Runwayarrow-down

How did Rent the Runway go from a simple idea to a $1 billion unicorn company that is disrupting an entire industry? The story of Rent the Runway is packed with teaching moments that every entrepreneur can apply to accelerate the growth of their own business. Jenny takes audiences through her entrepreneurial journey, breaking down exactly how to uncover valuable customer insights, tap into the world’s most powerful marketing strategies, create magnetic customer loyalty, and build a disruptive brand from the ground up.

Intrapreneurship – How Innovative Companies are Transforming from the Inside-Outarrow-down

As new technologies disrupt industries faster than ever, driving change from within is critical to success. Having led Walmart’s first tech incubator, Jenny created a template for innovation within the world's largest retailer. She reveals how entrepreneurial principles can be used by businesses of all kinds to grow revenue, drive innovation, and transform themselves into unstoppable forces.

Machine Learning & AI – Why Successful Businesses Find Balance Between Humans and Techarrow-down

Our world has been transformed by tech-driven solutions that promise efficiency and hyper-personalization. But as technology becomes embedded into every aspect of our lives, the feeling of human touch takes on the critical role of establishing trust and comfort with consumers. How do successful companies balance AI with a humanized experience to create customer loyalty? Drawing from her experience leading Jetblack to harness the power of machine learning and conversational commerce, Jenny shares her roadmap to the ultimate hybrid experience.

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Jenny was wonderful on stage and we appreciate her coming to the estate dinner. We’ve been so thrilled by the event and everything has gone smoothly!

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