In honor of our co-founders Hillary Kerr and Katherine Power’s new book, ($13), we’re kicking off an interview series featuring 17 questions (to parallel the book’s 17 chapters) about the work lives of inspirational female leaders who are at the top of their fields. We last spoke with . This week, another trailblazer is sharing her secrets to success—meet Jess Lee, CEO of online creative community, Polyvore.
In 2008, an enthusiastic, self-proclaimed “tech geek” named Jess Lee was on a career trajectory that her peers could only dream of. At only 24 years old, Lee had graduated from Stanford University with a BS in Computer Science, was proving her prowess as a leading product manager for Google, and counted as a close mentor. Yet something wasn’t right.
Each day, Lee led the charge developing My Maps at Google, and at night would spend hours on a then little-known website called . It didn’t take long for her to become a super user, crafting hundreds of virtual “sets” of shoppable products using the site’s simple editing tools. It was artistic, tech-savvy, and fashion-focused—everything she loved.
So how did a passionate fan go from being a user to CEO? It took one simple email. On a whim, Lee decided to contact Polyvore founder Pasha Sadri with unsolicited, honest feedback. The email was blunt, critical, and opened with a smiley-face emoji—not exactly what you’d expect to impress the founder of the site. But it did. Sadri invited Lee to meet in person and asked her to join the company as its first employee.
Fast-forward to 2016, and things have rapidly changed. Lee is now “honorary co-founder” and CEO of Polyvore, the digital world’s largest community of tastemakers. More than , with hoards of users using it to curate mood boards, shop products, and express their fashion, beauty, and home décor styles. Lee oversees a growing team at Yahoo! HQ in Silicon Valley, thanks to a fortuitous sale to now-mentor and CEO Marissa Mayer in 2015.
Here, the fierce boss opens up about the qualities she looks for in employees, shares the surprisingly simple uniform she wears each day, and reveals her unexpected morning routine. Take note—this is what it takes to score your dream job, from someone who knows.
“As the CEO of Polyvore, I have three responsibilities. It’s kind of like being the captain of a ship. The first is to set the vision for the company, which is like explaining our ultimate destination and why it’ll be awesome once we get there. The second is to make sure to hire a great team, which is like finding a crew that can plot the course to that destination. The third is to make sure we don’t run out of money, which is like having enough food and water for the journey.”
“The CEO role is constantly evolving as the company evolves. Just when I finally get good at my job, it changes underneath me!”
“I wore what I thought was a safe option—a white button-down shirt and black slacks—but it turns out that Silicon Valley has a super-casual dress code, so in actuality, I was overdressed.”
“I’d love to have a conversation with Joss Whedon, who created some of my favorite TV shows filled with realistic, awesome, strong female characters. I’d like to understand what inspires his creativity and how he honed his storytelling ability.”
“I use a combination of Facebook, Reddit, and Twitter to find the latest news. Also, the Polyvore team posts interesting industry news in a Slack channel, so I get news crowdsourced by people I work with.”
“The journey of building a startup is always hard. We made a lot of mistakes along the way. Many of them came from not focusing enough on doing a few things well.”
- “Doing your homework. We’re always impressed when candidates showcase their knowledge of our product. The strongest candidates have studied our app, become users, and learned its strengths.
- “Bringing solutions. If possible, try to identify some areas for improvement or suggestions how the company can do better. Show your knowledge and how you can contribute in a greater way. On one occasion, a candidate prepared a beautiful, polished booklet that used all of Polyvore’s fonts and colors. I was impressed by his passion for the company, his suggestions, and his attention to detail.
- “Problem-solving abilities. I also try to understand if candidates have the ability to break a complex problem down into smaller pieces, because that shows their problem-solving ability. People will always be challenged to do something difficult, and how you break it down shows a lot about your thought process.
- “Humility and self-awareness. Since collaboration and teamwork is so important at Polyvore, we look for people who are self-aware. Sometimes I’ll ask ‘what is the biggest misconception people have about you?’ which requires you to think about how other people perceive you.
- “Motivation. I like to ask, ‘What’s the most rewarding thing you’ve ever worked on, that you’re most proud of?’ You learn a lot about what the person cares about, what they prioritize, and whether they say ‘I’ or ‘we.’ Then you just drill down a bit more to understand how they contributed in the project.”
“My power ‘suit’ is an all-black outfit with a leather jacket and some knuckle duster rings. I hate wasting time picking out an outfit in the morning, so I’ve optimized my wardrobe for efficient decision-making, gravitating toward simple black and white items with interesting details.”
“Quirky and transparent.”
“I love going on Polyvore and seeing some of the beautiful creations from our style community. It’s inspiring to see how our users express themselves through fashion, beauty and art. Sometimes I’ll draw inspiration from them and try my hand at styling some of the latest trends or planning an outfit for an upcoming cosplay convention.”
“Be honest and upfront with your boss that you’re leaving, give plenty of notice, and make sure you have a clear transition plan. Don’t try to get a counteroffer if you aren’t really planning on taking it. Don’t burn bridges on your way out.”
“Yahoo has an amazing cafeteria with a great menu. They serve everything from pasta to sushi to make-your-own-salad to Indian to stir-fry. I tend to go for whatever has the shortest line, which is usually soup and a salad. During the work week, I optimize my lunch for speed and efficiency, but on the weekends I like to enjoy my food and try different restaurants.”
“A common mistake is not asking enough questions for fear of revealing that you don’t know exactly what you’re doing. It’s better to ask questions, so you can learn quickly and become productive.”
- “imjennim: One of my favorite YouTubers, style vlogger Jenn Im.
- “guy_tang: Guy Tang is another favorite YouTuber, a hairstylist who specializes in doing amazing color.
- “quayaustralia: Quay Australia is one of my favorite sunglass brands.
- “hotdudesreading: Who doesn’t like hot, smart guys reading books?”
>“In the morning, I like to catch up on my favorite YouTubers like , , and while brushing my teeth. Throughout the day, I’m checking Snapchat regularly. In the evenings, I use Tumblr to keep up with my favorite fandoms and Reddit because it’s the front page of the internet.”
>“Always take the more challenging path. Even if you don’t succeed, you’ll have learned a lot.”
“I’m working on a fun secret project that I can’t talk about, but it’s one of the things I’m currently most excited about. Aside from that, we’re having fun testing new experiences with our community—some of which you may see in the near future!”
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