Overstock.com President: 'It's Okay to Explore'

Stormy Simon, president of the e-commerce company, shares insights on the importance of taking risks in retail, such as accepting bitcoin payments.

Stormy Simon is no stranger to innovation. As president of Overstock.com, Simon has helped usher in forward-looking initiatives such as the early adoption of bitcoin payments. She was also a driving force behind Overstock.com's transformation from an online liquidator into a "first run" e-commerce company.

In January, the National Retail Federation named Simon a "Power Player" on its List Of People Shaping Retail's Future, and described her as one of the "fearless leaders who never shy away from what others may see as insurmountable challenges." 1to1 Media caught up with its 2009 1to1 Media Customer Champion to discuss her willingness to take risks and the retail trends that she's watching.

1to1 Media: What is an example of a challenge you had to overcome to improve the customer experience at Overstock.com?

Stormy Simon: As a pioneering e-commerce company, I had to figure out things that haven't been done before. Here we were, in this environment in 2005 where the Internet was beginning to change the way people shop. Overstock was selling things in a different manner than what many people were used to. Our customer service experience back then was completely outsourced.

But customer service for e-commerce was still being defined. Outsourced agents were familiar with catalog services but they didn't quite understand e-commerce. I was lucky to have the department assigned to me and decided to bring everything in-house so that they [customer service representatives] could better understand what we were trying to do. Building an in-house customer service team was a major challenge, but we succeeded and we continue to do customer service in-house today.

What retail trend would you say is overhyped and, conversely, what trends are you excited about?

I'm not sure any trends are overhyped, it just depends on where you sit in this space that affects your sense of hype. And whether you're a brick-and-mortar or pure play e-commerce retailer or both, everyone has their own challenges.What I'm excited about is cross attribution for identifying customers across their devices and understanding how they shop by demographic. I do think vendors are making advancements in cross attribution and determining that it's the same person who signed in from different devices, but no one has figured it all out yet.

Millennials and Gen Z are also very exciting to me. What's interesting about them is 16 years ago, when we started Overstock, we were teaching people how to shop online. These generations, however, have grown up with e-commerce at their fingertips. They have a very different view of retail and how it works. You don't have to convince them that it's a good way to shop. What we have to do is reach them when they need to be targeted. It's been fun exploring how we're going to stay relevant with them.

What's your strategy for being relevant among younger shoppers?

We have to be where the Millennials are, which is on their phones and apps like Instagram. Millennials spend about 75 hours every month using apps, so we have to be there. There's a fine line between doing that without infringing on their space, though. We're tiptoeing through it right now, but that's how you do it. You start identifying where your customers are and how they spend their time.

As president, how do you promote a culture of innovation that's manageable so that you're not trying to do everything at once?

That's another fine line. It's back to Millennials when you talk about the workforce. The new generation has to be inspired at work. They have to feel a part of the mission and they have to feed their soul every day. If you have that, people are better able to innovate. But you still have to balance the things that need to get done with dreams of doing things differently. You can't just have a group that innovates or a group that just does today's job. They have to feed each other, ideally. I personally look to hire people who are smarter than me. That's the first check. It's also just as important that someone can do the job as the job being a fit for that person. It's a balancing act that never stops.

Overstock was the first retailer to accept bitcoin payments; what lessons has the company learned from accepting a new form of payment?

First, we did it very quickly. The team handling it was able to get us up and running in just a few weeks. Being open to different forms of payment is important. It's about not being afraid of what's coming. We were already familiar with credit card payments and PayPal. Then bitcoin came along. We learned that it was okay to explore and try new things.

Do you segment or personalize interactions based on bitcoin payments?

Not really. They're just shoppers. There are a few similar interests among them [people who pay in bitcoin], but it doesn't show up on a demographic.

How you do personalize your interactions?

Every retailer has a recipe for personalization. The basic ingredients are involved, such as what did they click on, where did they enter from, and what did they buy? From there you can do time of day and other attributes like that, but everyone has a recipe and so do we. The recipe is never complete. You always want to get more personalized. The more data you can pull in, the better off you'll be.