Will Young spends his days thinking about online fashion—specifically, figuring out ways to make it fun, convenient, interesting and enticing for consumers to shop and order fashion from the Zappos website. A former programmer who now serves as director of engineering for the Amazon subsidiary, Mr. Young runs Zappos Labs. His small San Francisco-based group of designers, developers, project managers and content specialists say their mission is "exploring the future of Zappos."

Mr. Young is considered a Digital Trailblazer for pushing digital innovation to make Zappos a destination for products people aren't expecting from the retailer and for exploring nontraditional experiments such as social shopping and user-generated content to expand the company going forward.

He took time out recently to talk about his 4½-year stint at Zappos and his perspective on e-commerce today.

Q: As a Digital Trailblazer, you're doing outstanding work to further digital marketing. Why have you chosen digital as the focus of your career?

Mr. Young: Digital is fun, and I'm constantly learning. Even 15 years after I started in the industry, I don't know what I'm doing all the time. Every time we feel that we finally have it cracked—something like Facebook advertising, for instance—something new emerges. There is never a shortage of challenges.

Q: Tell us about a moment in your career that was pivotal.

Mr. Young: There is one moment that sticks in my head. As someone with "Tiger parents," I was getting pushed to succeed, to get a promotion, keep rising. But in one of my jobs before Zappos, I was getting burned out and felt that I really wanted to quit. Right then, my boss said, "If you stay, we'll make you a general manager of the product line." At that moment, that sounded like the worst thing ever to me. It was an epiphany moment. It helped me center my career around finding what I wanted to do. That's hard out here in Silicon Valley. There's a lot of pressure, for example, to be a startup founder even if you never have wanted to do that.

Q: In your opinion, what's interesting or telling about the way the millennial generation communicates, makes connections or builds relationships—qualities that influence your job as a marketer?

Mr. Young: Those of us who are a little older, we think everyone uses email. But especially as you look at the younger end of the millennials, email is being phased out of their lives. We at Zappos shoot millions of emails a week. What is that going to look like in a few years?

I was opening a conference meeting recently and just for fun asked, "Who's had a Snapchat strategy?" It was a throwaway, silly question. But someone put their hand up and talked about how "Our girl is a Snapchat girl."

It's really important for any online group to investigate new channels. As a lab team we are able to create ideas and try things without worrying about the ROI. Zappos has an appetite to try things, but there are lots of brands that won't touch those new channels. They will get left behind.

Q: How important is failure—the freedom to fail—in the digital environment?

Mr. Young: [It's] huge. The nice thing about digital is that you should be able to try things quickly. We may spend six months on something and learn in one day that it doesn't work. Quicker failure is what we embrace. But one thing about young, scrappy startups is that they launch, iterate until they get it right and then, if they need to, give up after maybe 10 tries. In contrast, big companies launch, and measure and kill. They rarely take the time to fix things.

Q: How important is social media in encouraging consumers to shop for fashion online?

Mr. Young: My wife is into fashion, and three-quarters of the people she follows on Instagram are fashion bloggers, trendy people. She is not spending time reading the traditional magazines that talk about fashion trends. But no one has cracked the code and gotten consumers to buy while on Instagram.

What is nice about Pinterest is that a lot of it is organic. The activity we see is not because of the pins our marketing team does. We get lots of traffic when people pin organically. That is what brands hoped would happen with Facebook.

Q: What parts of your marketing strategy keep you up at night?

Mr. Young: My problem is "The 700 Post-its Problem." After we finish a brainstorming session at Zappos Labs, we are all tired and sweaty, and we have 700 great ideas posted up on our wall. What keeps me up at night is wondering whether we are pulling off the right Post-its.

Q: What hobbies do you still prefer doing the old-fashioned, nondigital way?

Mr. Young: I am [climbing] Mount Rainier. It's my first experience with mountaineering, my first time with an ice axe and crampons. I and four other Zappos people are joining a group of climbers.

Q: Name a surprising place where you find inspiration.

Mr. Young: Our Zappos headquarters is in Las Vegas. You might think that would be the last place you'd find creative inspiration, but what's happening in downtown Las Vegas is amazing.

About the Sponsor

Today's trendsetters are also today's digital leaders. The Digital Trailblazers Series profiles some of the industry's most visionary digital executives—those pushing the boundaries in digital marketing. For more on this series, including intelligence and insights from Quantcast, visit the Digital Trailblazers Hub.

Quantcast is a technology company specialized in real-time advertising and audience measurement. As the pioneer of direct audience measurement in 2006, Quantcast has an in-depth understanding of digital audiences across the Web, allowing marketers and publishers to make the smartest choices as they buy and sell the most effective targeted advertising on the market. More than 1,000 brands rely on Quantcast for real-time advertising. More information is available at www.quantcast.com.