Overstock Design & Strategy

I led the visual, interaction, and prototyping for this project. I also collaborated with a small team on research and strategy.

People buy and go

While Overstock generates more than one billion dollars annual revenue, most users come to the site through ads or the allure of coupons. As a result, the percentage of one-off purchase is high and the repeat user engagement is low, causing high user acquisition costs and low customer lifetime value. The goal of this project was to increase user engagement and loyalty.

Going wide and wild

With such a challenging and open-ended problem in hand, we started with free form brainstorming involving all stakeholders. The goal was to generate high volumn and high variety of ideas. Some are incremental, some are radical.

Brainstorming session @ overstock HQ

Process: weekly design sprint

Based on initial assessment and internal enthusiasm, we consolidated all the ideas into the three directions. Because each direction has distinct value propositions, we explored various permutations for each and tested all of them with users through weekly design/research sprint. The goal was to choose one that can realistically fit into Overstock’s implementation timeline with the potential to generate meaningful results.

Testing three initial concepts

Following are the three initial directions we explored and experimented with:


Builds relationship by being useful. Helps people make the best purchase decision everyday. Lets people take a photo of any products offline and compare them with products and prices on Overstock.


Not too confident about imposing a new user behavior. Partnership with third-party image-recognition companies causes uncertainty and may not fit into the timeline Overstock was looking to implement.

"Inspire Me"

Builds relationship by being personal. An easy way for people to discover, personalize, and connect with brands and products that fit their lifestyle. Provides style consultation through a concierge service, adding a human touch to online shopping.


Too much upfront cost for the concierge service, and virtual showroom required high degree of curation. Many of personalization infrastructures haven't been built out yet.

"Engage Me"

Builds relationship by being fun and rewarding. Strategic placement of a collection of engaging games throughout different parts of the user journey, focusing on conversion and long-term engagement.


1. Has the potential to build a habit-forming shopping experience while improving brand-customer relationship.
2. It creates meaningful distinctions from other shopping apps in the market.
3. This concept also effectively uses Overstock's strength in delivering high quality product at discount price.

Where people should have fun

As we continued to iterate and test the “Engage Me” concept, we identified two main touch points in the user journey where embedding meaningful gamified experience can enhance the shopping experience while not disturbing the flow.

1) Wishlist, because it is where people browse items that they considered but not yet purchased. A small, fun, and rewarding game can lighten up the experience and increase direct conversion from the list.

2) Post-checkout. People have already completed their goals (purchases), so their core searching and shopping flow wouldn't be disrupted. Moreover, it's an opportunity to connect people with the Overstock brand, and provide incentives for future purchases (increase loyalty and LTV).

Making wish come true

A lot of people use the Wishlist feature to research and collect items they want, but a large portion of these users do not complete a purchase at all. Worst still, they may proceed and buy from competitors (such as Amazon). We want a game that can effectively prompt people to act on their Wishlist, while forming a habit of browsing and shopping from Overstock. We used Nir Eyal's Hooked Modal as the foundation for thinking about this concept.

Whack a mole

Whack a mole and get discounts for an item on your Wishlist.


While many users smiled on the interactions, we thought the whole game was too off-brand.

Pick a card

Pick a card and get discounts for an item on your Wishlist.


Too simplistic. It’s not engaging enough that people would come back and play again everyday.

Spin the wheel

Spin the wheel and get discounts on specific items. People can choose to “take it” or “spin again” for 3 times max.


It’s the right mix of luck and decision making that people are engaged enough to play it regularly. Intuitive, easy, and fun. This was by far the favorite of many people we tested.

Final Spinning Wheel Prototype


“I feel like this is more interactive and responsive than how most sites work. This is a lot more unique, it’s a very different perspective of shopping.”

“Having the games feels more fun and instant. Otherwise you would have to wait for a code to be emailed, and it feels like you could get higher than what’s emailed here.”

“oooh, this is really fun.”

Checkout, check out the trivia

How might we create a checkout experience that will turn one-time shoppers into repeat loyal customers through gamification?

The game needs to have the right level of difficulty, and people earn different amount of rewards based on their performance. A game like Trivia is ideal for this. Also, because people have already completed their purchases, it was not disruptive to have a more involved game experience. Moreover, trivia is a great way to embed brand related questions and educate people about Overstock's brand, products, and core values.

Initially, the experience was not well received, but I discovered a little trick in the user flow that completely changed people’s reactions.


“What? This is confusing. Why should I play a game here? This feels random.”


“hmm this seems interesting. Let me play it.”

Interestingly, when people are dropped into the Trivia automatically, they felt it was random and confusing. But when presented the option to play, all of the 10+ users we tested opted in to play the game.


"If I have the time, I would choose to play the trivia game. Having completed a purchase, it feels good. It’s like my reward for having it done."

"Oh interesting, I didn't know I could find electronic products on Overstock. I thought they only sell furnitures."

"I like that you can make a donation here with your rewards. I didn't know Overstock was doing these charity things before."