Jennifer Fleiss Biography
Jennifer Fleiss is the head of Jetblack, a firm operating within Walmart’s startup incubator, Store No. 8 and is the co-founder of Rent the Runway and as of 2018. Fleiss was born and grew up in New York City. She graduated from Yale University cum laude with a BA in 2005 and later attended Harvard Business School. While at Harvard she met future co-founder of Rent the Runway Jennifer Hyman, and graduated with an MBA in 2009.
Jennifer Fleiss started her career in the Strategic Planning Group at Morgan Stanley crafting long-term company strategy. She then moved on to Lehman Brothers’ Asset Management Group where she was responsible for analyzing business growth opportunities through acquisitions, international expansion and new product strategies. Fleiss a natural entrepreneur, founded an essay-editing and coaching service for college applicants, and built the company into an online tutoring service.
Fleiss presents on topics such as the sharing economy, female leadership, entrepreneurship, and industry trends in retail, social media, and marketing.
Jennifer Fleiss Rent The Runway
Jennifer Fleiss alongside Jennifer Hyman co-founded Rent the Runway in November 2009. Rent The Runway is an online service that provides designer dress and accessory rentals. Before opening brick-and-mortar retail locations in New York City, Chicago, Washington, D.C., San Francisco, and Los Angeles, Rent The Runway was initially a purely e-commerce company. Hyman is the current CEO of the company.
Fleiss helped to grow the fashion rental service to a reported $100 million in revenues in 2016 and finally turn a profit. She stepped down as the head of business development at Rent the Runway in 2017 but remained on the board of Directors.
Both co-founders, Jennifer Fleiss and Jennifer Hyman own 13% of Rent The Runway. Jennifer Fleiss is credited with vertically integrating the Rent the Runway operation in the company’s 40,000 square foot distribution center in Secaucus, New Jersey.
Jennifer Fleiss Code Eight | Walmart
Recode reported that Code Eight was testing a personal shopping service in New York City, and had posted a job listing for “a trusted personal shopping companion that surprises and delights the high net worth urban consumer.”
Fleiss was tapped to head up Wal-Mart’s Code 8, a stealth company based in Silicon Valley that aims to create more personal, one-to-one shopping experiences through artificial intelligence and machine learning. The startup falls under the umbrella of Store No. 8, the retail giant’s first-ever technology incubator, created in an effort to compete with Amazon’s e-commerce business.
Jennifer Fleiss On Rent The Runway
What is Rent the Runway, in a nutshell?
Jennifer Fleiss: You log into the website. You pick out a dress that you love and we send it to you in two sizes to ensure the perfect fit. Then when you’re finished, you pop it in the mail and send it right back to us.
Here’s how it works:
Becoming a member of Rent the Runway is free. When the customer is ready to place her first order, she is just asked to provide her name and email address. The cost ranges from $30 to $800 for a 4-day rental, and the customer’s credit card is charged. We send a free backup size with the customer’s order to ensure a perfect fit. The customer ships the entire order back at the end of her rental period. Dry cleaning is included in the rental cost.
You have a lot of members who are women in the financial industry. Can you give us some insight into who some of the most notable women who have rented dresses are, and for what kind of occasions?
Jennifer Fleiss: Oh my goodness, we have a lot of celebrities rent dresses, news anchors and others. As you can imagine, they are photographed on the red carpet and constantly need to turn over their wardrobes. I think every woman today is her own celebrity. Every woman has the need to look and feel her best every day, and because she’s on social media, she has her photo taken and posted, and needs to turn over her wardrobe.
As somebody who has your pulse on the fashion world, what advice do you have for women trying to find their personality through fashion?
Jennifer Fleiss: I think it’s great to look through magazines, to look online—there’s so many great blogs these days — but to incorporate that with a little bit of what you’re comfortable in and what works for you. I know for me, personally, convenience is a big factor. So, having an outfit that I can wear from 8 in the morning all the way to 10 at night sometimes — that’s versatile — is important. I stress having something that feels comfortable to who you are as a person. So as much as you want to mix something from the runway, or a fun trend from a blog, always go back to who you are as a person, what makes you comfortable, and confident. We want every woman to feel her best in clothing — that’s the point here.
As a women entrepreneur, how did you go about dealing with the difficulties of raising money?
Jennifer Fleiss: When we launched the business, we were really among the very few women who had raised venture money and pitching to a group of male VC’s can be challenging, particularly when it’s such a female-oriented concept. We really thought through what are ways we can get men to identify with the need of a woman to constantly wear new things. We thought creatively about how we could give them that perspective of the amazing, confident feeling a woman could have when she puts on a great dress.
What advice do you have for women trying to make that transition from the financial industry into other careers?
Jennifer Fleiss: We hear a lot of women coming to us and interviewing trying to get out of the financial industry, just feeling like it’s not a great fit for them and they’re looking for something that’s more authentic and maybe more invigorating for them. I think having this all-around athlete mentality of ‘I’m going to be open and willing to do anything’ goes a long way. I know for us at Rent the Runway, culturally, that really matters; you’re rolling up your sleeves, you’re willing to dive in, you’re admitting you’re not an expert necessarily in anything, but you have this go-getter attitude and I think that’s really helpful. Then, just putting yourself out there and being open to failure, because not everything is going to be a success. Trying a bunch of different things, I think you’ve got to give yourself this ability to try, fail, and try again and be a little bit amorphous as you’re starting to shift industries and try different things. You also likely need to be open to a pay grade shift or adjustment, at least for a certain amount of time, if you’re coming from the finance world. Finding something you’re passionate about is incredibly worth it.
What keeps you up at night?
Jennifer Fleiss: Our team is growing so quickly. We just raised another round of funding, and we’ve got a couple new branches to our business: one is retail with retail stores now, and the other is our subscription business. We’re growing with the mission of constantly challenging every woman to think about their closet differently. Getting those two businesses off the ground is really important right now.
How do you keep your work separate from raising children?
Jennifer Fleiss: Definitely, a lot of cooperation with my husband — and strong dialogue and communication there, too. Also, having a work environment that is supportive of women. For example, my daughter comes into the office and it’s an exciting part of my life that everyone knows about. It enables me to be really open if there’s a moment I need to take off to go do something for her or be with her. Not feeling like it has to be a choice always one way or another, but feeling like both can coexist because the culture here is very accepting of women as mothers. It lets me feel more comfortable if there are things I have to do as a mom that takes me away from the workplace.
How do you manage your money with your husband?
Jennifer Fleiss: A lot of it has happened naturally just from where our own interests or skill sets lie. My husband bears a huge amount of the travel, logistics, and bill paying. I wind-up doing a lot related to the household and kids. I think it’s just natural things we both feel good at, and feel are enjoyable parts of managing a household. There’s enough stuff at home that it’s a job unto itself!
You must see a lot of investment opportunities from your vantage point? Anything tempt you?
Jennifer Fleiss: I’m constantly tempted because I so much want to support every entrepreneur. I think it’s great that New York has become such a hub for entrepreneurship. At the same time, it takes a lot of time to be able do that, so I’ll often spend time as an adviser or just providing mentorship or guidance to other startups, but for the most part, I’m just so focused on what I’m doing here that it consumes me.
How do you spend your weekends?
Jennifer Fleiss: A lot of sleep lately. We rotate with my husband. Kids birthday parties. And then being plugged into work with 1-5 hours of work over the weekend that help me get ready for the week ahead. I’m still into using physical calendars to lay things out.
What are keys to success?
Jennifer Fleiss: One tactic I love is thinking through the activities that energize you in a day — if it’s a type of meeting or going out for lunch or out of the office that give you a boost. You can spread them throughout the week and I find that they can help carry you forward.
Ask other people for input. Especially when we started the business, getting advice from other people was really important. It started with this bias toward action: let’s get started. Dive in. But also speaking to experts it he industry and getting their guidance along the way.
Who’s influenced you most?
Jennifer Fleiss: Mom is definitely a big one — just keeping a positive attitude, especially starting a company. A lot of that came from her. There have been so many advisors that I’ve had. Alfred Lin comes to mind — the Zappos CFO who helped in founding the online shoe store. He was really helpful as I thought of the warehouse and our cost structure. My great co-founder, with many complementary skills, has also been a great figure in my life. We have a wonderful first investor in Scott Friend from Bain Capital. Scott was an entrepreneur himself, so having him from both the VC perspective but also someone who has started his own business has been a wonderful complement to our style as founders of the business.
What do you splurge on?
Jennifer Fleiss: Massages — I love them. Time wise, I work out every day to keep me sane — I’m a big runner, and I like spinning. It helps me escape from all the thoughts in my head.
Guilty pleasures?
Jennifer Fleiss: I like frozen yogurt and sweets and going out with my daughter, now 3. She has an entrepreneur Barbie I gave her. She gets exposure, and just being in the office she sees what it is to work.
You come from the financial industry — an industry that wants more women. How can women leverage their sense of fashion to be successful?
Jennifer Fleiss: A lot comes back to confidence. The more you can think, ‘What helps you bring your best confident self to an interview everyday? Whether it’s what you’re wearing, or aspects of your body posture or facial expressions’ — that’s incredibly important. I often work with a career coach and it’s been incredibly rewarding. They help me with how to tee-up and frame a conversation and think of it from the other person’s perspective — maybe starting a conversation by acknowledging what might be on their mind and creating an avenue for an open dialogue respectful of the other person.