It would be all too easy for your inner high school mean girl to instantly dislike Jenn Hyman. Not only is she girl-crush gorgeous, but she heads up Rent the Runway, which is, you know, like only one of the most talked-about fashion and tech companies on the planet. She has a fabulous wardrobe, a Harvard pedigree and a striking poise. She speaks with the articulateness of a well-seasoned media pro, but manages to sound completely genuine while doing it. When you listen to her talk, you realize quickly that she’s admirably intelligent, but in a way that’s the opposite of annoying and pretentious. Instead, she’s funny, frank and unscripted – all refreshing in world where so many CEOs speaking publicly rely on hyperbole and canned comments.
That was my impression when I met Hyman during an event held in San Francisco last year, and it held up during her visit to San Francisco for last week’s Marie Claire-sponsored Ready. Set. Startup. event at Ruth’s Chris Steakhouse, where she answered questions about the early days of Rent the Runway and its growth since launching in 2009.
Most of the women in the room – the night was aimed at Bay Area professional women and packed to overflowing by the event’s start – were hoping to glean some entrepreneurial wisdom from Hyman, and she didn’t disappoint. If you’re looking to sponge up some of that success stuff she’s clearly got in spades, here are 7 Hyman-inspired ways to get ahead, all based on her comments during the San Francisco event.
1. Ask big. You just might get what you want. Early on in her career, Hyman told those assembled at the event that she’d actually created a new position for herself at Starwood simply by noticing a new market opportunity (weddings) and convincing the head of the company to give her a budget to build a program focused on the area. Later, when she was getting Rent the Runway off the ground, she guessed Diane von Furstenberg’s email and contacted her out of the blue (she got the meeting). She also cold-called Anna Wintour (she got that meeting, too).
2. Take risks for an idea you really believe in. An anecdote Hyman mentions often when talking about her career is the time she and RTR Co-Founder Jennifer Fleiss used a credit card to buy 11o dresses at Bloomingdale’s in order to start their company. They hedged their bets a bit by only buying dresses in their sizes.
3. Be prepared to play the game (or get your nails done). “I’ll never walk into a fashion meeting without a manicure,” Hyman told guests. It’s not because she’s high-maintenance, but because a top fashion executive once told her she’d do well to show up better groomed at future meetings. She took the advice to heart. Playing along with an industry’s customs and operating within its bounds is not, Hyman says, a sign of insecurity or weakness, but rather one of respect. And respect is an important thing to have when you’re new to an industry and trying to make an impact.
4. Know your worth. When she was first hiring new employees, Hyman says she spent her time trying to sell prospects on the job. “I was so amazed that someone wanted to work with me,” she recalls. Over time, she flipped tactics and began bringing on new employees with something to offer the company. The new approach yielded much better hires. Also, ask for raises and negotiate terms to your advantage when you deserve it, Hyman suggested. Doing both worked out in her favor.
5. To be a great leader, sometimes you have to let go of the reigns. “Probably the biggest flaw a lot of CEOs have is micromanaging,” Hyman said. Though it was her instinct to be hyper-involved in her company’s day-to-day, she discovered that her employees felt more empowered and performed better when she let them take ownership of their own departments and projects.
6. Be the brand. Hyman admits she rents dresses as many as five days a week. How’s the for towing the party line?
7. Look closely, and you’ll find people that can help you in the strangest places. Hyman told the audience how a New York Times story that brought much attention to the company came to be (media geeks like me love these kinds of stories). She happened to spot a junior reporter’s email address in the marketing database of names they’d collected pre-launch. She reached out on a whim. The reporter’s story ended up on the cover of the business section and rocketed RTR from obscurity into the limelight. P.S. The reporter, Jenna Wortham, is now one of the top business writers at the Times.