Next time you stand in front of your closet with no idea what to wear, remember there’s an army of wannabe Anna Wintours and Rachel Zoes on Polyvore.com ready to offer inspiration. In just a few clicks, these aspiring stylists, artists, and creative kids-next-door can turn out a trendy head-to-toe look by tapping Polyvore’s vast database of designer apparel and accessories. Leading the charge is Jess Lee, cofounder and VP of product of the online platform that straddles the intersection of style and social commerce.
Since 2007, Polyvore has been providing an online platform for the fashion-minded to create “sets” from over 42 million images that encompass everything from Chanel nail polish to Burberry shearling coats. These carefully composed collages of branded products are wielding considerable influence over the fashion industry. Polyvore users create over 35,000 sets a day and the site attracts over 11 million unique visitors per month, making it the most-visited fashion destination on the web.
Polyvore’s profitability, generating revenue from targeted promotions with brand sponsors, prompted some to copy its business model and others to shift entirely. For instance Style.com, Condé Nast’s online repository for fashion news and runway photos, took a back step into print , while Google’s Boutiques.com shut down entirely last month.
For a self-professed tech geek who loves to draw, Lee tells Fast Company that Polyvore’s growth affirms she made the right move four years ago. Lee left a solid job at Google Maps to join the startup team at a time when fashion and technology were far from cozy. “Our friends worried about random users having creative control over 100-year-old brands,” Lee recalls. Now Polyvore members are outfitting the likes of Bergdorf Goodman’s Linda Fargo  and seeing their designs on the runways. “I’m excited to be a part of that form of acceptance,” says Lee.
Here’s what else she told us about making decisions, changing directions, and encouraging virtual conversations.
Rooted in Creativity
Lee’s made no secret of the fact that she’s really into comics (she owns over 1,000 comic books) and would like to write and illustrate a graphic novel someday. The creative bug bit early, and Lee can recall telling her parents in high school that she wanted to pursue an art degree. “They said no; they’re Asian,” Lee says, laughing. “So I ended up at Stanford in computer science.”
It wasn’t until much later that Lee says she discovered she wasn’t the next Picasso. However, she continued to indulge her creative side, eventually getting hooked on making sets  at the nascent Polyvore. Her takeaway from that "failure?" “At Polyvore, I work on a platform that allows empowers other people to be creative, that is in some ways more satisfying than being the artist.” The same goes for managing her staff. “Rather than doing something myself, if I can help someone else do it, it’s really rewarding.”
Lee’s first work experience came at her mother’s side. While the family lived in Hong Kong, Lee’s mother ran her own business doing English-to-Japanese translation. “Mom paid me to count the number of words in her translation,” Lee explains, a task that taught her the importance of detail. But Mom provided an unspoken lesson: “It was never unusual for a woman to run her own business. She set that example.”
Later on, Lee’s first “proper” job was at a small entertainment magazine in Hong Kong that she likens to Time Out NY. “It was kind of a startup,” says Lee, which meant that everyone had to wear different hats. Like the time the food writer suddenly quit and Lee--just 18 at the time--was sent off to review a high-end restaurant. “That experience taught me to be scrappy and take on a lot of responsibility.”
These early experiences went on to color Lee’s career, first when she sidestepped an opportunity at Intuit in favor of the less-established Google, and again when she made the risky leap to Polyvore .
It’s also influenced her management style. “I think I am very hands-on because when Polyvore was smaller everyone had to do everything. I wrote code, sold ads, did dishes, and went on food runs,” she says, admitting that now it’s sometimes hard to let go.
One thing she did learn managing half of Polyvore’s growing staff (now totaling 32) is that happy people are productive people. “I always try to make sure people are excited about what they are working on,” she says. And if she needs inspiration or the answer to a difficult question on managing teams, she often finds herself referring back to blog posts penned by well-known angel investing partners Marc Andreessen and Ben Horowitz.
Organic Growth and the Wisdom of Crowds
Though she credits the experts, Lee is quick to point out that Polyvore’s evolution from a generic tool to create mood boards has been driven by its users. “It’s definitely been organic from early on. Our fan base has been a guiding light. They are the ones who showed us that fashion was the right first vertical.” Now, even the ad programs featured on Polyvore  are ones that were originally developed for the user community.
Challenges and Changing Attitudes
Though Polyvore’s been an influence, Lee maintains that social media landscape at large continues to be the disruptive force behind the democratization of fashion. “Social media gives everyone a voice. Designers can choose to participate in the conversation, but the new world of transparency is a big challenge,” she says. However, it’s one that can be tackled just by participating in an authentic way. “Fans appreciate that. The problem is when you don’t engage.”