The CEO that changed how women shop may just do it again with her new company

In 2009 Jennifer Fleiss and Jennifer Hyman changed how women shopped when they launched Rent the Runway, the clothing rental platform that quickly expanded from just dresses to nearly every item of clothing a woman could need, to children’s clothing to furniture. And now Fleiss, as the CEO of Jetblack, she is trying to change the world of conversational commerce.

If that term sounds a little less familiar to you than e-commerce, just think of it as any time we shop via voice automation or a text. Jetblack, the text-to-shop service that is the first company to launch from Walmart’s technology incubator, Store No. 8, is basically a personal shopping delivery service with a concierge (via voice or text) you can make shop for you and even give you customized recommendations.

Fleiss, a mother of three, sees this platform as being very useful for busy parents or just busy people in general. Once you text or say your shopping request to the Jetblack team they will find the right product match for that consumer and have it delivered the same or next day, for no additional cost  – they’ll even gift wrap it. Think of the holidays potential.

Fleiss told Ladders, “Our lives are busier than ever and the ability to send a text or speak a voice command and get curated product recommendations, answers on critical questions about a product, and dump mental to-do lists of many purchases I need to make to run my household felt like a dream.  Conversations with thousands of parents reaffirmed that shopping had become a chore and there was a need for a seamless service where you could shop for any product and have it delivered quickly in a consolidated tote.”

According to research from Jetblack, only 3% of consumers surveyed actually use voice assistants, but one-third of all Americans use these platforms and 30% have a voice assistant in their home so the potential is clearly there. Ladders spoke with Fleiss about her new company, leaving Rent the Runway as the company was hitting its stride and what she looks for in employees.

Courtesy Jetblack

Who does Jetblack really serve? Who do you think it will help the most? I know you as a busy mom really wanted something like this but it definitely has a millennial appeal as well?

As an entrepreneur, I’ve always focused on solving real-life problems that I am personally experiencing. Consumers today are busier than ever, and they’re looking to technology to help simplify everyday life. The best solutions not only find them ways to save money but save them time as well. We’ve been able to respond to this new need by leveraging a widely-used technology – texting – to create a totally new e-commerce experience with Jetblack. Jetblack is a membership-based shopping service powered by conversational commerce.

“Our text-based platform along with our curated recommendations have made shopping much more streamlined while giving vital time back to the consumer to spend it focusing on what matters most to them. Its audience is everyone and anyone looking to save time in their lives and streamline their shopping behaviors.

You have talked a lot about starting RTR and the challenges there. What did you bring from that experience to start Jetblack or was it a lot easier this time?

Rent the Runway evolved from my and Jenn’s perspective as women in our twenties identifying big trends, like social media, that were changing women’s fashion needs.  Being the end consumer was critical to disrupting the fashion industry.

In my experiences at Jetblack and Rent the Runway, identifying with the end consumer and constantly gut-checking innovation against real customer feedback has always been the key to success and longevity. This is what allows us to grow with our consumers and adjust to their changing behaviors.  The importance of building a trusted brand that resonates with the end consumer and enables them to build a relationship within rapidly changing industries is another commonality.

Were you scared when you left Rent the Runway? Did it feel risky or really exciting?

I have a passion for developing a company in its early stages, and that drive ultimately led me to my decision to leave my day-to-day role at Rent the Runway. I have to hold myself back on starting and working on new concepts all the time so that energy and that drive to work at a really early stage startup started to get a little bit lost as Rent the Runway grew.

I was still itching for that 30-person team in a room, all crammed there working on an early-stage concept. As an entrepreneur, my work is embedded in my life and I am constantly using my own life experiences to think of creative solutions that sometimes lead to multi-million dollar businesses.

Courtesy Jetblack

Where would you like to see Jetblack in a year? How about five years?

At Jetblack, we are focused on a different trend in retail and how that will change consumers’ lives in the next five years and beyond. Jetblack’s focus is conversational commerce which translates to the ability to shop via a text message conversation and, down the road as AI improves, voice recognition technology. For now, Jetblack delivers via courier and bike messengers, but in the future, as it expands across the country (it is currently only available in Manhattan, The Hamptons and Brooklyn), I anticipate that Jetblack could even have its own delivery vehicles.

In five to seven years we hope to have the system mostly automated and less reliant on humans. This is a long journey and I think we were aware of that going in. Walmart primarily views the company as a research hub on AI and voice shopping. Some pieces of the business could very readily be applied to the broader ecosystem in time.

What is your best productivity hack?

Jetblack – The amazing service has truly transformed my life and is now a part of my everyday routine. It helps me balance being a mom and entrepreneur by taking away the hassle of going to the store or searching online for products that I need. The service allows me to stay productive while making sure my family is taken care of and everything gets done.

The Class by Taryn Toomey – bang my workout, therapy, and relaxation out in an hour.  I usually coordinate to go with a friend or colleague to motivate and also get some rare time to catch up!

Airpods – Airpods are my go-to tech product. They allow me to multitask on the phone, listen to podcasts while I’m packing school lunches or on a run and work on the go.

What do you look for in an employee when you are hiring?

At Jetblack we are looking for creative problem-solvers who have a can-do attitude, are self-starters and take ownership.  I also look for someone who is flexible as we constantly need to pivot and change as an early-stage business.  A positive, upbeat attitude is a must in the startup world where there are many ups and downs and you need people who are optimists, continuously charging to make the impossible work, while being enjoyable to work alongside!