Jenny Fleiss

Why organisations work with Jenny Fleiss

• She has built a consumer business from a Harvard Business School idea to a publicly listed company, and a separate venture inside Walmart’s Store No. 8 incubator. That gives a board credible answers on both routes into a new market.
• She speaks from inside the operating cockpit of conversational commerce and AI-driven personalisation, not from a strategist’s deck. Jetblack used text and machine learning to handle real customer requests at scale.
• Her seat at Initialized Capital and prior investing work put her across hundreds of early-stage decks in e-commerce, consumer and AI. She can tell a corporate audience which startup behaviours are worth importing and which are noise.
• She brings board-level perspective from listed and private companies including The Lanvin Group, Shutterfly and Rent the Runway, which lets her translate founder language into governance language an audit and risk committee will understand.

Biography highlights

• Co-founder and board member, Rent the Runway, the New York-listed designer rental company she started with Jennifer Hyman in 2008.
• Founder and former CEO of Jetblack, the conversational commerce startup launched inside Walmart’s Store No. 8 incubator in 2018.
• Former Partner at Initialized Capital, the seed-stage venture firm, where she led e-commerce, consumer and AI investing.
• Independent director, The Lanvin Group (since 2022); board member, Shutterfly (since 2019); board member, Arteza.
• MBA, Harvard Business School; BA in Political Science, Yale University, cum laude.
• Recognised on Fortune’s 40 Under 40 (2012), Inc. 30 Under 30 (2010), Forbes Disruptors 2013, and Fast Company’s Most Influential Women in Technology.

Biography

Renting a designer dress through a website was not an obvious business in 2008. Jenny Fleiss and Jennifer Hyman started Rent the Runway from a Harvard Business School idea and turned it into a publicly listed consumer company. The work needed to be done in unglamorous places: dry cleaning logistics, returns flows, fit data, inventory forecasting. The brand sat on top of an operations problem.

A decade later, Walmart asked her to build a startup inside its corporate body. Jetblack was a text-based, AI-assisted personal shopping service for high-spending New York households, incubated inside Store No. 8. The product taught Walmart what conversational commerce actually costs to run, what humans still have to do behind the model, and where machine learning genuinely earns its keep in retail.

That double track, founder of a venture-backed unicorn and intrapreneur inside a Fortune 1 retailer, is what makes her useful in a corporate room. She has lived the trade-offs between speed and brand risk, between founder autonomy and parent-company governance, between AI promise and operating reality. Her investing work at Initialized Capital and as an angel adds a third lens: which early-stage signals are worth a corporate’s attention and which are theatre.

Her board work at The Lanvin Group, Shutterfly, Rent the Runway and Arteza puts her in front of the same governance questions her audiences face. Boards want innovation, but they also want explanations.

Key speaking topics

• Building and scaling consumer internet businesses
• Conversational commerce and AI in retail
• Corporate venture building and intrapreneurship
• Customer data and personalisation at scale
• Female founders and the funding gap
• Early-stage investing in consumer and AI
• Board governance for innovation programmes

Ideal for

• CEOs and divisional presidents in retail, consumer goods and direct-to-consumer brands
• Heads of innovation, corporate venture and new ventures inside large incumbents
• Chief digital, chief data and chief AI officers responsible for customer-facing AI deployment
• Founder communities, accelerator cohorts and women-in-business leadership programmes

Audience outcomes

• A clearer view of which startup behaviours translate into a corporate parent and which collapse on contact with it.
• A working vocabulary for what conversational commerce and AI personalisation actually require to run at scale.
• A board-level frame for sponsoring internal ventures: what to measure, what to protect, when to wind down.
• A grounded read on the current early-stage consumer and AI investment market from someone who has sat on both sides of the table.