How Jetblack CEO Jennifer Fleiss Is Leading the Evolution of E-Commerce

"In order to be efficient, we have to be able to be even more personalized than ever before," the Rent the Runway co-founder explained.

Rent the Runway co-founder Jennifer Fleiss.
Rent the Runway co-founder Jenny Fleiss. Jenny Fleiss

Jennifer Fleiss has been quite busy since leaving Rent the Runway, the company she founded with her Harvard Business School classmate Jennifer Hyman.

Over the past year, Fleiss has helped co-found and head Jetblack, a text-to-shop service and the first company to launch from Store No 8, Walmart’s tech incubator. Jetblack, which she started with Jet founder and CEO Marc Lore, marks Fleiss’ second foray into the world of e-commerce.

SEE ALSO: Rent the Runway Joins $1 Billion Female-Run Startup Club

The service is a conversational shopping platform that allows busy consumers to text nearly any shopping request to the Jetblack team. Observer recently spoke to Fleiss about what it’s like to start a second e-commerce company, being one of a handful of female serial tech entrepreneurs and work-life balance as a mom of three.

Many know about Rent the Runway’s memorable origin, but tell us about your decision to continue in e-commerce with Jetblack and what that transition has been like. 
I love the early stages of businesses. I think it’s where I’m my best self and where I have the most value. When Rent the Runway was about nine-years-old or so, Mark Lore reached out to me. He’s been an advisor and mentor of mine since the early days of starting Rent the Runway, so we both knew each other and our skill sets very well, and he asked me to co-found Jetblack with him. Mark had been put in the role of CEO of Walmart’s eCommerce U.S, so obviously that takes up most of his time. But part of what he felt happy about was, in addition to focusing on making sure that the digital business for Walmart was strong, thinking of ways to push to the future. So not just focusing on the “today,” but also “for tomorrow,” and Jetblack is kind of the first manifestation that we thought about in terms of how we can do that.

The proposition of coming in to be the CEO and working on the business with him was very exciting. It was definitely what I thought about, being able to leverage all that I learned at Rent the Runway and disrupting behavior, along with leveraging Walmart’s infrastructure. This includes things like legal, real estate, HR, finance—all of the nuts and bolts pieces of starting a business that you normally spend time on early on. It’s really plug-and-play, in the way that the incubator was set up. So, I was able to focus on a consumer problem by taking point and plugging pieces, which I love the most.

Right. Being incubated, which is sort of like working within a large corporation as an independent startup, seems to present a bit of a different challenge in tech. Can you tell us about working on the brand to grow and how this experience differed from the last time you started a company when you were in business school.
Yeah, the first thing is that there are all kinds of infrastructure resources to pull from, with the biggest one being fundraising. This business is fully owned and funded by Walmart right now, and that’s meant that I can focus my time on the consumer and pinpoint problems, finding product market fit. But a lot of the infrastructure has already been put in place—even things like recruiting support, we’re able to leverage Walmart for that. There’s obviously a lot that we definitely need to work on and enhance in terms of how it works, but I think it has the potential to be the fastest and best way to start a business. And I’m excited to be part of shaping this incubator while building the first business in it.

In terms of some of the minimum viable product testing we did at Rent the Runway, that’s something we also do here. Also the idea of “how do you get an early stage concept out to the consumer and have them test the product and learn from your consumers?” I put a lot of that into play here as well, so that piece of the process felt very similar. The element of starting from that consumer pinpoint that I knew and felt passionately about was also very similar.

For Rent the Runway, Jen [Hyman] and I were both women in our 20s who had a lot of events, who didn’t have as many dresses to wear as we wanted. We didn’t really like the fast fashion options, and we felt social media was compounding this problem. But with Jetblack it’s “I’m a busy mom with three kids and constantly needing to purchase everything from paper towels to kid birthday gifts to you know… clothing for myself to wear to work (or to workout).” It can be really time consuming and inefficient. It’s made shopping into a chore, to the point where I had people, like my husband and housekeeper, texting me about stuff that we needed for the household. Sometimes, I would text myself as a reminder. This customer behavior of texting-to-shop for any product you want, that’s what Jetblack came out of—both a passion and a need that I felt as the consumer.

Jennifer Fleiss
Jetblack co-founder and CEO Jennifer Fleiss attends the Jetblack Summer Shopping Cocktail Night event on May 14, 2019 in New York City. Bennett Raglin/Getty Images for Jetblack

Yeah, it seems like a tech-infused version of personal shopping, which is much more different than what we think of as the stereotypical department store personal shopper. 
The idea here is to combine the convenience of e-commerce with the personal attention that you’d have with a personal shopper or personal assistant. We’re actually getting back to the interaction you might have had years ago, when you’d walk into a store and interact with a sales associate who’s knowledgeable about the product. It’s someone who takes the time to get to know you, and you can have an interesting back and forth conversation to figure out the best product for you.

E-commerce has stripped some of that away recently, and while it’s a very efficient interaction, it’s made shopping into a chore and very transactional. What we’re trying to say is: “You know what, you can still have that back and forth interaction that you have with the sales associate, but given the advances of technology, you can now have that over text messages.” And eventually, it would happen over a voice interaction. I don’t think that’s going to replace in-store shopping, or e-commerce, or shopping on apps, but it’s a broader definition of omni-channel. How I think of consumer behavior evolving is by adding additional tools that make shoppers’ lives more and more efficient, and sometimes that means using them all together. Adding text and voice as additional tools, combined with physical stores and e-commerce websites, will lead to the best, most efficient consumer interaction possible.

It’s something we’re seeing more of these days. We’ve sort of returned to the idea of customization and attention, with e-commerce coming full circle and borrowing from retail’s interaction-heavy strategy. Perhaps at the end of the day, shoppers want someone to explain how something works or make recommendations, not just get a product shipped to them in a box. 
Absolutely. If you think of shopping over text or shopping over voice, you have to personalize more, because I can’t show you more than a couple of options at a time. Imagine texting someone like, 40 options, let alone thousands on the internet. The importance of getting to know you and your preferences is higher than ever before. The idea is if I want to use shorthand to ask for “a birthday gift for Julia,” knowing how old my daughter Julia is would be helpful, right? And that’s how people would speak, whether it’s to a shop associate who knows you or to a personal assistant or an interior designer. We’re trying to implement those sorts of interactions into a more scalable format. But in order to be efficient, which is the primary rule, we have to be able to be even more personalized than ever before.

Because in this case, you’re not just relying on an algorithm. Though I’m sure machine learning is obviously involved, a human customer service rep is needed.
Yeah, with Jetblack, it’s a combination of agents and bots. We have agents behind the scenes who are leveraging a dashboard that we built, and the dashboard has a lot of automated tools. It has many types of filters that will automatically pop up, depending on who the customer is. So the moment we get someone’s text, we know who it is and have a pre-filter based for, say, their children’s age or other preferences. It will pull up the recent paper towels someone has ordered if they ask for it. It really depends on the intricacy of a question, and if it’s a category that you’ve kept on. If it’s something in the realm of a recommendation—like “I need a birthday gift for a seven-year-old”—we’ll know the right questions to ask up front to help refine the considerations. Eventually, we’ll become better and able to service more and more customers quickly.

Jennifer Fleiss
Jetblack CEO Jennifer Fleiss attends a Galentine event hosted by Jetblack and Roxanne Assoulin on February 5, 2019 in New York City. Bennett Raglin/Getty Images for Jetblack

On a more personal note, as a millennial mom of three, you’re probably asked a lot about the “having it all” trope. With two companies under your belt and many women’s initiatives done with your Rent the Runway co-founder Jennifer Hyman, what are some of the values you’re bringing to the new company/ Especially given that Jetblack is housed within a large corporation?
It’s really critical to have women and moms, and people of all diverse backgrounds, involved in starting businesses—because the reality is that you start businesses that draw on personal paths you identify with. Given that we have a diverse population, the more diversity reflected in entrepreneurs and leadership, the better we’ll be able to solve consumer needs.

With Rent the Runway and Jetblack, they’re both tools that enable women to save time and hopefully be successful at home and at work, if they chose to do that. I also had my kids coming to the office at Rent the Runway and here, which I think is not only fun and lighthearted, but also [allows] those in the office who don’t have kids to witness the chaos that ensues when children are around. It also helps to step into the shoes of many of our consumers who do have kids.

Accessible childcare has also been a hot topic in the industry lately. What are your thoughts on what tech can do about this issue for women and mothers?
There is a lot of progress that’s been made, but obviously still way more to come. It’s also about having work environments where it’s comfortable or acceptable for kids to be in the office sometimes. Having more flexible maternity options, maternity leave options or working options. It also could mean a company’s approval of working from home, or working remotely on occasion, to allow women time to transition back into the workplace. For example, when I was at Rent the Runway, I helped create a maternity plan that offered mothers the ability to phase back in more gradually and work part-time for a period of time, because we really wanted people to come back. We’re also seeing that shared daycare type of option now. I think having corporations lead the way is really helpful in helping achieve this goal.

How Jetblack CEO Jennifer Fleiss Is Leading the Evolution of E-Commerce