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Jess Lee's Journey From Polyvore Superuser to CEO

Vikram Alexei Kansara sits down with Jess Lee, co-founder and CEO of Polyvore, a community-driven fashion discovery site that aims to create 'an army of Anna Wintours.'
Jess Lee, co-founder and CEO of Polyvore | Source: Polyvore
  • Vikram Alexei Kansara

MOUNTAIN VIEW, United States — While working for Marissa Mayer as a product manager at Google, Jess Lee became an obsessive user of a recently launched service called Polyvore, which allowed users to "clip" images of clothing and accessories from fashion sites and online stores and assemble collages, known as "sets."

A Polyvore set by MyChanel

As a child growing up in Hong Kong, Lee had dreamt of becoming a writer of manga comics and Polyvore appealed to her creative instincts. She spent upwards of two hours per night on the website and soon began bombarding co-founder Pasha Sadri, a former product manager at Yahoo, with a series of "complaints" on how Polyvore could be improved. It was the first step of a remarkable journey that would see Lee rise, in five short years, from Polyvore superuser to CEO, a position she assumed in 2012, making her one of the few female chief executives in Silicon Valley.

Lee, who is also an honourary co-founder, never went to business school. Instead, she learned on the job, doing everything from writing code to selling advertising. But the plucky former product manager (“if you don’t challenge yourself, then you won’t be learning”) has been instrumental in helping Polyvore attract over 20 million unique visitors a month and build out a profitable business model based on affiliate marketing fees and native advertising. The company declined to disclose financial results, saying only that Polyvore crossed over into profitability in 2011 and has been cash flow positive since 2012.

BoF sat down with Jess Lee at the company's headquarters to talk about her journey from Polyvore superuser to CEO, the virtues of taking the more challenging path, and her overall vision to combine the influence of Vogue with the scale of Google to unleash an "army of Anna Wintours." 

BoF: Let’s start at the beginning. What were you doing before Polyvore?

JL: I went to Stanford, studied computer science and thought I would become an engineer. Then I got a call from Google and they said I should interview for the Associate Product Manager program. I ended up talking to people, including Marissa Mayer, who encouraged me to take the more challenging path and try something hard that I didn't think I’d be able to do. I was pretty sure I could be an engineer, but I didn’t know if I could be a product manager and lead teams of people. It was a very good learning experience.

At some point I transitioned to Google Maps and when the product launched, we thought people would use it to plot things like “My favourite places in London” or “My running trails.” But it was used for a number of larger things that we hadn’t anticipated. At the time, there were wildfires in California and a radio station started using Google Maps to plot where all the fires were and millions of people started looking at the map. That’s when I realised: “Wow, it’s really great to build tools for people; to build a platform and see what people do with it because they always surprise you.”

BoF: What initially attracted you to Polyvore?

JL: A friend of mine, another Google Maps product manager, said, “Hey you should check out this start-up my friend is working on called Polyvore.” When I first used the site, I totally fell in love.

BoF: What did you find so compelling?

JL: The self-expression. When I was little I would just draw all the time. I told my parents I wanted to write manga as my career and they were like "No!" You know Asian parents, they were like "Doctor, lawyer or judge!" But one of the reasons I was attracted to Polyvore in the first place was because it's artistic — that, and the community aspect. I would make sets and instantly get feedback from other people, who I started to meet on the site.

Shortly after that, I wrote an email to the founders with a list of complaints, like “Hey can you fix all this stuff? Can you add rotate? Can you change the name of this button because it’s confusing?” And [co-founder] Pasha [Sadri] wrote back saying “Why don’t you come here and fix this stuff yourself? We should talk.”

BoF: What convinced you to take the plunge?

JL: I always knew I wanted to do a start-up. My mom’s an entrepreneur and she said, “You should always be your own boss.” But I ended up going to Polyvore because it was a product that really resonated with me. Plus, the first year on the job at Google the learning curve was crazy. I had no idea what I was doing half the time. But then, the learning sort of plateaued and I knew if I went to Polyvore I would have to learn all kinds of things because there was nothing there. We would have to figure out how to get an office space. We would have to figure out how to make money — do all these things I had never done before.

I was really following that same advice that Marissa [Mayer] had given me before: “Go where it’s going to be challenging, so you can learn a lot.” I didn't join with any expectation that this was going to be a big business. At Google, they teach product managers to build something that users will love and the money will come later. I just thought it was a great opportunity to own something that I really loved using myself — and I knew there were changes we could put in place to make Polyvore more appealing to a broader audience. When I met Pasha, I also really liked him. I liked all the founders.

BoF: Polyvore has had a series of management upheavals over the last few years. Pasha was the company’s first chief executive, followed by Sukindher Singh Cassidy, who became CEO briefly, before Pasha took over again. When you took the reins in 2012, you were the company’s third chief executive in two years. What happened? And how did you rise to the top job?

JL: The first stage of any product-driven company is building the product, attracting users and getting product-market fit. That’s what we were trying to do in the beginning, which is why it made sense for everyone there to write code and get the product working. Then we brought in Sukhinder. She’s a really good leader with a lot of operational and sales abilities. But at that time, we were still working on product-market fit, so there was kind of nothing to sell. I think it was a little bit too early. We weren’t ready for Sukhinder and I think she also realised that.

But during that same time, there were certain things that just needed to get done, like we needed to find an office. We would look around the team and ask who was the crappiest engineer, which was me [laughing] so that became my job! Then, we started to get calls from advertisers, which also became my job, because somebody had to do it. The first one was Piperlime, who called and said "We have $10,000 to spend this quarter, what can we do with you?" I looked around and said "Errrr… You can buy a contest." That was when we first started to build our advertising products. I didn't have any preparation. It just needed to happened and I did it. By that time we had also started to add affiliate revenue to the site. I built the early foundation and did some of the first sales myself.

Pasha is an awesome product and technical person. He’s one of those rare engineers who’s not only good at writing code and being a [software] architect, but he’s really really good at coming up with clever product ideas and polishing the user-interface. But everyone in the team who wasn’t in product and engineering reported to me. Then at some point we realised that we had a certain degree of product-market fit and the CEO role transitioned from being about building the product to building the company: hiring, cementing the team. That’s when we decided to switch roles. He moved into the CTO role and I moved into the CEO role. That was about a year and a half ago.

BoF: Polyvore is often described as Vogue meets Google, but the two companies are so different. One is a publisher. The other builds platforms. How does Polyvore merge these very different approaches?

JL: The aspect of Vogue that Polyvore is trying to capture is being the place where you can find great taste and discover trends. Anna Wintour's vision for what fashion should look like is pretty amazing. But we use technology à la Google to find, not just one Anna Wintour, but an army of Anna Wintours. We're trying to collect tastemakers around the world and give them a platform.

Remember, one of the key reasons why Anna Wintour is influential is because she has distribution. She has millions of readers through Vogue, who are essentially her followers. But with Polyvore, you as an individual who live in a tiny town somewhere can also build a million followers and actually influence what products those people wear and what purchases they make.

You can’t easily print your own magazine and get it into every newsstand everywhere — but with the Internet you kind of can. The Internet democratises the trend setting hierarchy and gives more people a voice. But of course, you have to prove yourself. You have to have a distinct point of view that resonates with people. On Polyvore, there are people who have really good taste and there are enough people who follow them so that they are able to build authority.

BoF: What problem does Polyvore solve for end consumers?

JL: Polyvore is also about discovery. There are so many designers and so much clothing to choose from. I think one of the unsolved problems in online shopping for fashion is how do I find the thing I want to wear in the first place. It’s so different to shopping for consumer electronics, where you can refine down your choices by factual things like how many megapixels a camera has.

With fashion, there are millions of products and you have to decide what matters based on your personal taste. And on Polyvore, you can find people whose taste is similar to yours, then see what sets they’re building, what items they are using and how they are styling things and get a kind of personalised stream of content containing things that you are going to want to wear and buy.

When I flip through a magazine like InStyle, there are a lot of top trends, but there are only a small number of things that I would actually wear. That's because there are a finite number of pages, so you have to pick things that appeal to a wider audience, whereas there are people on Polyvore whose taste is much closer to mine. Polyvore offers personalised discovery.

BoF: How does Polyvore monetise the relationship with its users? What have you put in place to make the company profitable?

JL: Luckily, at the end of the day people come to the site to look at products, so it’s a much easier starting point compared to, say, Facebook where people are there to look at personal photos and it’s very unlikely they’re going to want to buy something. Putting the affiliate infrastructure in place was very important. And then on the advertising side, it's mostly CPM (cost per thousand impressions) advertising. We do native advertising, so you won’t see banners on the site. Instead, you’ll see products that are promoted or Polyvore sets that are promoted — ad formats that are more integrated into the user experience. [In terms of percentage contribution to overall revenue generation] affiliate is a bit bigger.

BoF: What about the data that Polyvore generates? What products millions of users are clipping and how they perform within the community is surely valuable information. What are you doing with the data?

JL: We use it internally to power our algorithms. We have thought about it as a business model, like if you were a brand you could see how your stuff (and your competitor’s stuff) is being styled and what the key trends are. But we believe in doing a few things well and have decided to focus on advertising for now.

BoF: Looking back at the remarkable arc you’ve travelled, from superuser to CEO, what have been the biggest challenges?

JL: With so many of the things I’ve done at Polyvore, it’s been my first time doing them. The first time I made an ad sale, they said “Ok great, send me the IO (insertion order)” and I was like “What’s an IO?” I was literally on the phone with them while Googling “IO.” It’s just been a constant stream of being asked to do stuff that I don’t know how to do, which has created a pretty steady stream of anxiety. But when you overcome those challenges, it’s incredibly rewarding.

Making money was a big challenge to overcome. Polyvore is now profitable and cash flow positive. But I went from being a product manager at Google, who was trained to never think about money to realising that I need to build a business. That was a major mental shift.

I’ve also learned a lot about team building. In my career, I’ve had the opportunity to try things for the first time and I’ve realised that’s an important part of attracting the right team — people should know it’s possible for them to rise quickly or have the opportunity to learn new things. To attract good people the environment also has to be very transparent and everyone has to be willing to listen to suggestions, no matter who they come from.

Another big lessons has been doing a few things well. There were a lot of times where we had to say no to things that were distractions and I think that’s one of the main reasons we’ve survived. There are only a few things that really matter in moving your business and it’s better to do those things really really really well, rather than doing a lot of things poorly.

BoF: What advice would you give someone who is 20 years old and aiming to build a career in fashion tech?

JL: Probably the same advice I got when I was 20 from Marissa [Mayer]. Always take the more challenging path. Even if you don't succeed, you'll have learned a lot. And another thing: there's a classic mould for CEOs and that's something I was quite worried about, as I don't really fit that mould of being super-extroverted and [adopts male voice] rallying the troops. I'm just not that kind of personality. I'm a little more introverted. I initially focused on the technical side of things rather than the business. But just because you don't fit the classic mould doesn't mean that you can't be a leader. You just need to find your own style and someone with a similar style who you can learn from.

BoF: Looking into the future, where do you see Polyvore in five years time?

JL: There are a lot of ways to grow. Some of the things we have to work on are new devices — iPad, Android. Then, there’s new verticals. The plans was always to be a broader platform. We started with interiors before focusing on fashion and we want to grow into other verticals in addition to fashion — anything you buy based on taste, the opposite of the way most people buy cameras — so probably home, wedding, baby, menswear. We look at what the community already does and it’s about expressing your lifestyle through the kinds of brands and products that you use: what you wear, what you put in your home. And then there are new countries. A lot of our traffic is international. But the site isn’t optimised for that.

BoF: Do you still make your own sets?

JL: Yeah I do! You can look at my profile. I still love to draw, but I don't have time and it takes so much longer than putting together a set. I also love it because of the community — the people who comment on my sets. I check in with them. It's a very friendly community. These are my peeps!

This interview has been edited and condensed.

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