Partner at Initialized Capital & Co-Founder, Rent the Runway and Jetblack
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.
- Rent the Runway, one of only 20 female-led "unicorn" companies in the U.S. to achieve a $1B valuation, went public.
- Jenny is currently a partner at Initialized Capital doing seed stage investing with a focus on e-commerce enablement, consumer and AI.
- She is also the 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.
- Jenny is a board member of The Lanvin Group (LANV), Shutterfly, and Yale Ventures and is an adviser to and investor in various businesses, many with female founders.
- She was 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, AI and Machine Learning.
Media
- Official Site: Rent the Runway
- Fast Company: Rent the Runway cofounder Jenny Fleiss joins growth equity firm Vo...
- Medium: Don't Waste This Crisis
- Medium: Embracing the Elbow Bump
- People: Rent the Runway Co-Founder Jenny Fleiss on Launching 2 Businesses with 3...
- Inc: Why Rent the Runway Founder Jennifer Fleiss Is Bullish on Web3
Videos
Biography
Jenny Fleiss is a Partner at Initialized Capital focused on seed stage investing with a focus on e-commerce enablement, consumer and AI. Jenny is an entrepreneur and intrapreneur, founding two scaled digitally native business from scratch: Rent the Runway and Jetblack. Jetblack is 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. Jenny is on the board of Rent the Runway (RENT), The Lanvin Group (LANV), Shutterfly, and Yale Ventures and is an adviser to and investor in various businesses, many with female founders.
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 Jetblack
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 Runway
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-Out
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 Tech
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.
Blend, Not Balance – Dream Boldly by Embracing Work & Life
Many women approach their career ambitions timidly. Many even hesitate to address the infamous question of “balance” in work/life. The weight of this question leads to less risk-taking, more apprehensive planning, and smaller goals.
Work and life are a BLEND, not a balance. Balance implies a choice — weighing two different things against one another. Jenny Fleiss built two companies, including Rent the Runway, and faced the balance question across different life stages as a young woman and a working mom.
Jenny shows audiences that the multitasking inherent in managing personal life, a household, and a family should be celebrated. Forced creative problem-solving will make you a better business leader, having children can make you better at time and stress management, and embracing the blend of our lives offers a striking perspective on just how far you can go.
Even in the lowest moments of your career or the entrepreneurial roller coaster, Jenny shows that by boldly embracing the blend — you can live without fear of dreaming bigger and going after it.
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FAQs
How do I book Jenny Fleiss for my event?
Contact CAA Speakers at (424) 288-2898 or speakers@caa.com to book Jenny Fleiss to speak at corporate or private events, keynote speeches, speaking engagements, workshops, fireside chats, motivational speaking, or virtual appearances.
Quick booking process- Email CAA Speakers with event details
- Get availability confirmation within 24 hours
- Review speaking fee and contract terms
- Sign agreement and finalize logistics
As one of the most influential talent agencies in the world, CAA handles all speaking engagements from contract to event day coordination.
Who is Jenny Fleiss's booking agent?
CAA Speakers is the preferred booking agency to contact for Jenny Fleiss’s speaking engagements. Contact speakers@caa.com for all Jenny Fleiss in-person appearances and keynote speaking requests.
Contact Jenny Fleiss's agent- Email: speakers@caa.com
- Website: caa.com/caaspeakers
- Response: Within 24 hours
CAA Speakers can check Jenny Fleiss's speaking calendar with direct access to availability and official pricing. While many websites may list Jenny Fleiss, CAA Speakers is the direct source for authentic information about availability and pricing.
What is Jenny Fleiss's speaking fee?
Jenny Fleiss's speaking fee varies by event type, location, and requirements. As a top keynote speaker, Jenny Fleiss's fee reflects their expertise and market demand.
Speaking fee factors:- Event type and audience size
- Travel distance and logistics
- Presentation length and customization
- Virtual vs. in-person delivery
Additional costs: Travel, accommodation, A/V requirements, and optional meet-and-greets.
Contact CAA Speakers at speakers@caa.com for Jenny Fleiss's current speaking fee and detailed cost breakdown.
How much does it cost to book Jenny Fleiss as a keynote speaker?
The cost to book Jenny Fleiss as keynote speaker includes their speaking fee plus travel and logistics expenses.
Total booking cost includes:- Jenny Fleiss's keynote speaking fee
- Travel and accommodation
- Technical requirements and A/V setup
- Optional add-ons like book signing and meet & greets
- Virtual presentations
- Local/regional events
- Off-peak booking periods
- Flexible event dates
Email speakers@caa.com for Jenny Fleiss's exact booking cost and customized pricing proposal.
How to contact Jenny Fleiss for speaking engagements?
Contact CAA Speakers at speakers@caa.com for all Jenny Fleiss speaking engagements.
Official contact for Jenny Fleiss bookings:- Email: speakers@caa.com
- Website: https://www.caa.com/caaspeakers/jenny-fleiss
- Response time: 24 hours
Include your event date, location, audience size, and budget when contacting CAA about booking Jenny Fleiss.
Is Jenny Fleiss available for virtual speaking events?
Yes, Jenny Fleiss speaks at virtual events with professional-grade equipment and interactive presentation style.
Jenny Fleiss's virtual event options:- Live virtual keynotes with Q&A
- Interactive workshops and breakouts
- Hybrid events (in-person + virtual)
- Pre-recorded presentations
Virtual events offer global reach, flexible scheduling, and reduced travel costs while maintaining Jenny Fleiss's engaging presentation quality.
Contact CAA Speakers for Jenny Fleiss's virtual event availability and technical specifications.
What events can I book Jenny Fleiss for?
Book Jenny Fleiss for corporate conferences, industry events, private functions, and virtual presentations. Jenny Fleiss customizes content for any audience size or event type.
Event types:- Corporate meetings and conferences
- Industry summits and trade shows
- Private executive retreats
- Educational institution events
- Virtual and hybrid conferences
Jenny Fleiss engages audiences from private executive meetings to large conferences with thousands of attendees.
Contact CAA Speakers to discuss how Jenny Fleiss can customize their presentation for your specific event.
Jenny Fleiss booking information and availability
Check Jenny Fleiss's speaking availability through CAA Speakers at speakers@caa.com. Book 3-6 months in advance for best date selection during peak seasons (September-November, March-May).
Availability factors:- Event date and location
- Speaking fee and budget
- Lead time for booking
- Peak conference seasons
- 3-6 months: Best availability
- 3-6 months: Best availability
- 2-3 months: Good availability
- 1-2 months: Select availability
- Under 30 days: Limited availability
Contact CAA early in your planning process to secure Jenny Fleiss for your preferred event date.
Book Jenny Fleiss keynote speaker through CAA
Book Jenny Fleiss through CAA Speakers for guaranteed authentic representation and professional event coordination. CAA is the preferred booking agent for Jenny Fleiss, with direct access to their speaking availability and decades of experience representing the world’s top keynote speakers.
CAA booking advantages:- Direct access to Jenny Fleiss's calendar
- 24-hour availability confirmations
- Professional contract negotiation
- Full logistics coordination
- Industry-leading client service
Trusted by Fortune 500 companies for their most important speaking engagements. Contact speakers@caa.com to book Jenny Fleiss for your next event.
Will Jenny Fleiss speak at private events?
Yes, Jenny Fleiss speaks at private corporate events, executive retreats, board meetings, and exclusive functions.
Private event types:- Executive retreats and board presentations
- Client entertainment and VIP gatherings
- Corporate celebrations and award ceremonies
- Private dinners and exclusive functions
Private event benefits: Customized content, enhanced interaction, complete confidentiality, and flexible scheduling.
Contact CAA Speakers for Jenny Fleiss's private event availability and confidential pricing proposals.
How quickly will I get a response about booking Jenny Fleiss?
CAA Speakers responds to Jenny Fleiss booking inquiries within 24 hours during business days. Complex requests or international events may take up to 48 hours for detailed proposals.
Response timeline:- Initial acknowledgment: Within 24 hours
- Availability confirmation: 24-48 hours
- Detailed pricing proposal: 48-72 hours
- Urgent requests: Same-day priority response
Include complete event details (date, location, audience size, budget) for fastest response times.
How far in advance should I book Jenny Fleiss?
Book Jenny Fleiss 3-6 months in advance for best availability, especially during peak speaking seasons. Early booking ensures better date selection and rate negotiations.
Recommended booking timeline:- 3-6 months: Optimal availability and pricing
- 2-3 months: Good availability
- 1-2 months: Select availability
- Under 30 days: Limited availability
Peak seasons: September-November and March-May book fastest. Contact CAA Speakers early for priority consideration.
How do I get Jenny Fleiss pricing information?
Get Jenny Fleiss pricing information by contacting CAA Speakers at speakers@caa.com with your event details. Receive detailed cost breakdown within 24-48 hours with no obligation to book.
For accurate pricing, include:- Event date and location
- Audience size and type
- Event format and duration
- Budget parameters
CAA provides transparent pricing with all costs included - speaking fee, travel, accommodation, and technical requirements.