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Keynote SpeakerJennifer Fleiss

Jennifer Fleiss is a keynote speaker represented by Rave Speakers, known for Co-founder of Rent the Runway; entrepreneur and investor reshaping retail & consumer tec. She delivers keynotes on Business Growth, Business Leaders, Entrepreneur, Future of Work, Innovation, Leadership, Technology, Women's Leadership for corporate events, conferences, and association meetings. Jennifer Fleiss's speaking fee is Please inquire. To book Jennifer Fleiss, contact Rave Speakers at (310) 614-8653 or visit ravespeakers.com.

Co-founder of Rent the Runway; entrepreneur and investor reshaping retail & consumer tec

Keynote SpeakerJennifer Fleiss

Co-founder of Rent the Runway; entrepreneur and investor reshaping retail & consumer tec

Business LeadersBusiness GrowthEntrepreneurFuture of WorkInnovationLeadershipTechnologyWomen's Leadership
Former CEO and co-founder of Jetblack, Walmart’s first text-based personal shopping platform
Co-founder of Rent the Runway, the company that reinvented how millions experience fashion
Entrepreneur, investor, and advisor helping brands innovate faster and connect with tomorrow’s customer.
Speaking Fee: Please inquire
https://youtu.be/gd7CQX8DeIY?t=131
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Co-founder of Rent the Runway and Jetblack, reshaping retail through innovation

Jennifer Fleiss is an accomplished entrepreneur, investor, and innovator best known as the Co-Founder of Rent the Runway, the company that revolutionized how millions of women experience fashion. What began as a simple idea-to rent designer dresses for special occasions-grew into a multi-billion-dollar brand that redefined access, sustainability, and consumer behavior in retail.

After scaling Rent the Runway into a household name, Jennifer went on to co-found Jetblack, Walmart’s first text-based personal-shopping service, where she served as CEO. There, she bridged e-commerce and convenience, pioneering how conversational commerce could transform the customer experience.

Today, Jennifer is a strategic advisor and investor in high-growth startups across retail, technology, and consumer brands. She speaks worldwide about entrepreneurship, innovation, leadership, and the evolving relationship between brands and customers. Her story-from early-stage founder to corporate innovator-offers powerful lessons in vision, persistence, and building businesses that scale with purpose.

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Sample Videos

Jennifer Fleiss (Rent the Runway) | Yale INSPIRE

Rent the Runway’s Early Days and the Future of Commerce with Co-founder Jenny Fleis

Keynote Topics

How do you turn a simple idea into a movement that changes an entire industry? Jennifer Fleiss shares her journey from co-founding Rent the Runway to scaling it into a billion-dollar brand that redefined fashion, access, and sustainability. In this inspiring and practical keynote, Jennifer takes audiences behind the scenes of launching a startup that challenged norms and reshaped consumer expectations.

Audience takeaways:

  • How to spot opportunities hidden inside consumer frustration

  • Lessons in building a brand that people love and trust

  • Navigating growth, funding, and leadership challenges in the startup world

  • How to innovate inside traditional industries by thinking differently

After leaving the startup world to launch Jetblack, Walmart’s first conversational commerce platform, Jennifer Fleiss learned what it takes to drive innovation inside large, established organizations. In this keynote, she reveals how to bring entrepreneurial thinking, experimentation, and speed into even the most structured corporate environments.

Audience takeaways:

How to create a culture of innovation within big organizations

Why agility and customer focus matter more than hierarchy and process

Strategies for bridging startup mindset and corporate infrastructure

The future of retail, technology, and personalized consumer experiences

From luxury fashion to big-box retail, Jennifer Fleiss has spent her career anticipating how people want to shop-and building the experiences that meet them there. In this forward-looking keynote, she explores how technology, data, and evolving values are reshaping the consumer landscape. Jennifer shares insights on personalization, sustainability, and convenience, revealing how brands can stay relevant in a marketplace that never stops changing.

Audience takeaways:

  • Key trends defining the next decade of consumer behavior

  • How brands can blend physical and digital experiences seamlessly

  • Why trust, transparency, and sustainability drive customer loyalty

  • The role of innovation and adaptability in future-proofing your business

Jennifer Fleiss’ message is sure to resonate with this year’s attendees and inspire them to achieve their own personal success

- Michele N. Siekerka, President & CEO, NJBIA

Inspiring keynote by Jennifer Fleiss… wow

- Informatica Women in Data

Frequently Asked Questions

Jennifer Fleiss delivers keynotes on Business Leaders, Entrepreneur, Future of work, Leadership. She is known for Co-Founder of Rent the Runway. Each presentation can be tailored to align with your event theme and audience goals.
To book Jennifer Fleiss, contact Rave Speakers at (310) 614-8653 or submit a booking request through our website. Our team will discuss your event details, confirm availability, and handle all logistics including contracts, travel arrangements, and on-site coordination.
Yes, Jennifer Fleiss is available for both in-person and virtual keynote presentations. Virtual sessions can be delivered as live interactive experiences or pre-recorded content. Contact Rave Speakers to discuss the best format for your event.
Jennifer Fleiss is Co-Founder of Rent the Runway. She brings a unique combination of experience including Co-Founder of Rent the Runway. Harvard Business School MBA. Forbes 30 Under 30 honoree. Audiences consistently praise her ability to inspire, educate, and deliver practical insights that attendees can apply immediately.
Yes, Jennifer Fleiss customizes presentations to fit the specific needs and industry context of each audience. She works with event organizers in advance to understand your business challenges and ensure the content is directly relevant to your team. Contact Rave Speakers to discuss customization options.
Yes, Jennifer Fleiss tailors each keynote to align with your event theme, audience demographics, and organizational goals. She works with event organizers ahead of time to ensure the content resonates with attendees and delivers actionable takeaways. Contact Rave Speakers at (310) 614-8653 to discuss how Jennifer Fleiss can personalize her presentation for your event.
Jennifer Fleiss co-founded Rent the Runway in 2008 with Jennifer Hyman while they were second-year students at Harvard Business School, after a conversation about Hyman's sister stressing about a dress for a wedding. They tested the concept with a pop-up at HBS, then launched the full marketplace in 2009. In keynotes Fleiss walks through how they raised seed funding without a working product, negotiated their first deals with skeptical luxury designers, and built logistics infrastructure at a time when no one believed women would rent designer clothes. The company went public on Nasdaq in 2021. The story translates well for audiences in retail, consumer technology, women's leadership, and early-stage entrepreneurship.
Jennifer Fleiss serves as an Operating Partner at Initialized Capital and as an active angel investor with backings in over 20 startups including ShopMy, Splendid Spoon, Pogo, Realworld, and Duffl. She also co-founded Roll Rider, a family travel product company, and sits on the boards of Shutterfly, Lanvin Group, and MelodyArc. That ongoing investor and operator dual lens gives her keynotes current case studies on which consumer and commerce models are working in 2026 and which are not, rather than only retrospective lessons from Rent the Runway. Audiences in retail tech, DTC, and venture-backed scaleups find specific pattern-recognition value. Contact Rave Speakers at (310) 614-8653 or visit ravespeakers.com.

Jennifer Fleiss Sample Videos

Jennifer Fleiss Keynote Speeches

How do you turn a simple idea into a movement that changes an entire industry? Jennifer Fleiss shares her journey from co-founding Rent the Runway to scaling it into a billion-dollar brand that redefined fashion, access, and sustainability. In this inspiring and practical keynote, Jennifer takes audiences behind the scenes of launching a startup that challenged norms and reshaped consumer expectations.

Audience takeaways:

  • How to spot opportunities hidden inside consumer frustration

  • Lessons in building a brand that people love and trust

  • Navigating growth, funding, and leadership challenges in the startup world

  • How to innovate inside traditional industries by thinking differently

After leaving the startup world to launch Jetblack, Walmart’s first conversational commerce platform, Jennifer Fleiss learned what it takes to drive innovation inside large, established organizations. In this keynote, she reveals how to bring entrepreneurial thinking, experimentation, and speed into even the most structured corporate environments.

Audience takeaways:

How to create a culture of innovation within big organizations

Why agility and customer focus matter more than hierarchy and process

Strategies for bridging startup mindset and corporate infrastructure

The future of retail, technology, and personalized consumer experiences

From luxury fashion to big-box retail, Jennifer Fleiss has spent her career anticipating how people want to shop-and building the experiences that meet them there. In this forward-looking keynote, she explores how technology, data, and evolving values are reshaping the consumer landscape. Jennifer shares insights on personalization, sustainability, and convenience, revealing how brands can stay relevant in a marketplace that never stops changing.

Audience takeaways:

  • Key trends defining the next decade of consumer behavior

  • How brands can blend physical and digital experiences seamlessly

  • Why trust, transparency, and sustainability drive customer loyalty

  • The role of innovation and adaptability in future-proofing your business

Check Jennifer Fleiss's Availability

[email protected]

(310) 614-8653

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Where our speakers are speaking

Inky Johnson is keynoting MDRT’s annual event in June.
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Ryan Leak just addressed The National Auto Dealers Association at their 2025 annual event.
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The NCA (National Confectioners Association) had their State of the Candy Industry Convention this month with Keynote speakers Jesse Cole and Molly Bloom who delivered inspiring messages on creative thinking and business resilience.
To say Janet Evans inspired me is an understatement. I had the great honor of being in the stadium in 1996 when the torch relay took place and have fond memories of the torch being handed by Janet to Muhammad Ali. Little did I know that amazing woman would come back later in life to inspire me with her version of the event. Thank you for your diligent efforts to bring Janet’s story to us.

Kathy Roche

Director of Meetings, Western & Southern Life

I just wanted to express my appreciation for having the opportunity to have Alex Honnold speak to my senior leadership group this morning. Alex was amazing: funny, articulate, open, humble, and very engaging. My group loved him and his presentation. Please let Alex know how much we appreciated him and his accomplishments, most notably his charitable foundation.

Robert Darby

CEO, Berkshire Hathaway Homestate

Our team has been working with Rave Speakers as a trusted resource for all of our keynote presenters at all of our events. They come in on-budget and are always there to support us. Rave Speakers is excellent to work with and an awesome partner.

Heidi Pascale

Senior Director of Experiental Marketing and Training, ASSA ABLOY Door Security Solutions

Thank you for all you did with booking Magic Johnson and being on site with him. It was so refreshing meeting you in person and having the service you provided. That was an invaluable experience for me and my team and I cannot thank you enough. Magic was amazing – there could not have been a better fit for our conference. Honestly, Mr. Johnson and Mel Robbins complemented each other better than I could have ever dreamt. The two of them made our conference.

Randie Vasso

Project Analyst, Heartland Payment Systems

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