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Jenny Fleiss has spent most of her recent career building companies that challenge the traditional consumer experience, and remove hurdles she’s experienced in her own life.

“With both Jetblack and Rent The Runway, it’s democratizing luxury and thinking of ways to change consumer shopping behaviors, which is my sweet spot and what I really love and enjoy. Both businesses largely were derived from experiences that I, as a consumer, had in my own life, and I think that’s the healthiest form of entrepreneurship, both in coming up with ideas and having the passion to drive those ideas forward,” said Fleiss.

When she co-founded Rent The Runway, the popular service for designer clothing and accessory rentals, Fleiss was in her 20s and looking to solve the age-old problem she and her peers were constantly facing: of a closet full of clothes and nothing to wear. Now, in a new stage of her life as a working mother, Fleiss is taking on the world of “conversational commerce” and the luxury consumer.

“With Jetblack, I’m a busy mom of three kids. I work, and I’m constantly looking for hacks and tools to make my life more streamlined and efficient. So Jetblack was born out of some of the pain points I felt. When I joined Walmart two years ago, as the first business in their tech incubator, I worked with Marc Lore to figure out, ‘What does e-commerce 3.0 look like?’ Combining some of the technology trends and innovations that were happening around conversational commerce — the ability to shop with your voice or over text message — with pain points I felt as a consumer, we arrived at Jetblack.”

In this week’s episode of The Glossy Podcast, Hilary Milnes sits down with Jetblack founder and CEO, Jenny Fleiss, to discuss the new age of e-commerce, Jetblack’s grassroots marketing approach and the way the company’s services pay off for brand partners. Edited highlights below.

Bringing brands on board
“When starting Rent The Runway 10 years ago, getting the first 30 brands was like pulling teeth, so we needed to go in with this mentality that we would probably be coming back 10 more times before they say yes. That has changed a lot for Rent The Runway since, but we learned a lot about what mattered to brands in just listening to their concerns. They wanted to know how their brand was going to be presented and protected, who was in the peer set they were going to be a part of, what the experience was that they could deliver for the consumer, and how could they tell the brand story or the amazing attributes of a product. In starting Jetblack, I brought that perspective with me, and that is why we decided to start with a really premium experience. Right now, every aspect of Jetblack feels very white glove, meaning that brands from the get-go feel that we have this really premium level of service. So much so that many of the brands have reached out to us proactively. For them, it’s a way to tap into this concierge, luxury experience, this new mentality of shopping, and get additional sales, but also reach a really compelling consumer who is shopping a lot. She has a lot of discretionary income, lives in New York and is a trendsetter in many ways. It’s an appealing consumer for these brands.”

Building a brand on conversational commerce
“One of the things that differentiates us is that we are really trying to build colloquial, natural dialogue in our service. So when we interact with our consumer, it’s the way you would talk to a personal assistant, or a friend, or a shopkeeper, which is what we believe is efficient, but is clearly not the approach that others have taken. For us, the premium feeling and the trust that it connotes is critical. If you’re asking me for a recommendation, you need to very much trust that when I send you three items, they’re at the right price point for good quality products.”

The power of word-of-mouth marketing
“I have a pretty specific view on marketing, and it’s something that naturally came about with Rent The Runway — it’s leveraging our point of view as consumers. How do we want to find out about new products and brands? What is the most effective, trusted way? With Jetblack, trust is key, because when you’re asking a consumer to change their behavior, you’re asking them to take a leap of faith, so it’s even more important that they hear about you from a trusted source. Very naturally, there are mom groups that evolve, there are groups at schools that evolve — so there was this natural virality in word-of-mouth with mom groups and communities. They were going to these blogs and forums and asking for product recommendations, and I related to that as a consumer. So it was like: Here’s a consumer who both needs advice on new products and is spending lots of time trying to get it. It’s also this natural, viral community — so if we can target some of those consumers, to start with, that will be a really powerful way to launch this by word of mouth.”