Leadership Lessons from CEO of Fashion Startup Rent the Runway

Leadership lessons from Jennifer Hyman, Co-Founder and CEO of Rent the Runway:

Be savvy. Be tenacious.

After Hyman had seen her younger sister waste too much money on designer dresses worn only once or twice, Hyman saw an opportunity to fix this problem that many women face. One Saturday night she thought, “What if we gave women access to this revolving ‘Vogue closet’- everything you’d ever want to wear?”

The next step for Hyman was to figure out if others thought her idea was solid. She asked a friend (and now her co-founder, Jennifer Carter Fleiss) for her opinion. Next, Hyman took things to the next level. She approached Diane von Furstenberg over email (merely guessing her address) and within minutes received an invite for her and Fleiss to visit the DVF headquarters in New York City. Throughout their meeting with Diane, Hyman peppered Diane with questions until the three were on the same page.

Hyman and Fleiss next ran some market research by hosting a few trunk shows at Harvard (where Hyman completed her undergrad). Once Hyman heard the reaction of one very ecstatic Tory Burch-clad sorority girl, she was even more convinced that she was onto something.

With the help of Diane and their test markets, Hyman and Fleiss learned that they could hit a whole new target market for luxury fashion designers, women between the ages of 15 to 45. Women known for regularly shopping at Zara and H&M and just under the target demographics of luxury department stores like Neiman Marcus and Bloomingdales. Rent the Runway could bring designer dresses to the everywoman, without the designer price tag.

Photo from the New York Times article covering their launch

Things were moving along well, when the Rent the Runway team hit another snag. Just before launch, after securing an exclusive interview to be published in Vogue, Rent the Runway’s PR team leaked their launch story. Ever the scrappy one, Hyman reached out to a (at the time) little known writer at the New York Times and got the story covered, and got it covered well. In 2009, this story became the sixth most emailed story of the year.

Be respectful. Be humble. Be open to learning.

One piece of advice Hyman received that’s stuck with her was to always have a manicure. Funny to openly say? Yes. How the fashion industry is? Definitely. As with every industry, fashion has a unique culture all its own. Hyman also learned along the way to remain very respectful of the designers she and her company work with. A brand doesn’t want to partner with Rent the Runway now? No problem. Hyman knows that just because someone says no in the beginning to working together, it doesn’t mean that once the designer and Hyman develop a relationship, that designer won’t reconsider. Besides, it’s nice to just build relationships so you can learn from new people anyway.

Hyman also has two mentors, from startups The Knot and Chegg, whom she greatly values. One is the woman she met in her early twenties whom she always looked up to. The other is a man who gives her the “hard coaching” she loves.

Be yourself.

Ah, such an overused phrase, but always true. While pitching her business idea to VCs, Hyman learned that she stood out from the flock (mainly male venture capitalists) by being her feminine self. She wore dresses and acted like a lady. Now, as the CEO of Rent the Runway more than two years in, Hyman can admit that she may be more emotional than most male CEOs, but does she see it as a negative? Absolutely not.

“It’s ok to be your authentic self at work,” Hyman says.

Be authentic, but be confident is her rule. Too often Hyman says she hears men boasting they are the right man for a big position (whether they are or not) and she notices that women don’t often do this. While being humble is important, it’s just as important to have confidence. Just within the past year and a half Hyman has started to realize that she’s confident in her leadership style and position within the Rent the Runway team.

I met Jennifer Hyman on Monday evening at Ruth’s Chris Steak House as part of Marie Claire’s Women in Business series. I also won the grand prize of the night!! But more on that later.

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