Multi-item Shopping


Macbook displaying a wireframe of a future design for a "shopping cart" experience when purchasing travel items

How might we allow users to shop for multiple trip items in one session?


Back on our legacy platform, customers were able to string together trip items within a single shopping path and purchase everything at once. When all of the products started migrating from legacy onto a single platform, these capabilities had to be turned off and deferred until all the products were on the same new platform. It’s consistently one of the most common topics of feedback we received from clients and all our competitors offer a way to do this. Now that all of the shopping products have finished migrating, we can finally reintroduce this capability. We really wanted to do it right, and think thoroughly through the experience.

In order to do this, the product lead set up a workshop and involved all of the necessary people. To inform the workshop discussions, we wanted to do our due diligence in researching and testing viable methods and bring our findings to the conversations.


1. Extensibility
  • Build a robust shopping platform with the flexibility to purchase any combination of flights, hotels, cars, or trains for any number of travelers.
2. Flexibility
  • Allow customers to purchase any combination of products – even those that don’t necessarily make sense together (two rental cars for one trip).
  • Allow for different origins/destinations and arrival/departure times for multiple people
  • Allow purchasing of multiple stand-alone products for different destinations and dates
3. Savings
  • Offer savings for customers as an incentive for booking products together
Multi-item shopping flow today. A user has to go through the entire path for each item they want to book.
Multi-item shopping flow today. A user has to go through the entire shopping path for each item they want to book.


Contributing designer & UX researcher

Designing, testing, and analysing different shopping methods

Over two one-week design sprints, myself and another UX designer worked closely together to brainstorm, solve, create, design, build, and test three different shopping path concepts. We complied our results and insights to contribute to the workshop in the most effective way possible.

Presenting insights during the workshop

During the workshop, my partner and I shared competitive analyse and how we can learn and adopt ideas from other companies, as well as detailed insights from our testing and how they should be considered in the work going forward.


Defining the North Star Vision

Putting our research to work

Over three days in April 2019, about 25 of us got together to think through the problem, define the scope, and set milestones for the overall project. After defining the problem and setting the context, my partner and I shared all of the content and learnings from our research to the group. This really helped everyone step into the user’s shoes, as well as somewhat dispel the strongly held opinions about specific solutions. Throughout the workshop, we continuously revisited the research results and the wireframes to help guide the conversations.

Example of a low-complexity flow (with me looking very focused)
Example of a low-complexity flow created with our wireframes and research (with me looking very focused)
Defining the direction

After going through all of the exercises and considering all of our unique perspectives, we landed on a few key features that would be table-stakes for our north star vision.

1. Review page before entering Checkout
2. Progress and Save indication
3. Not everything needs to be booked at once
Northstar basic user flow
Northstar basic user flow
No items found.
No items found.

Implementing the plan

One thing I learned in this process is how to present my findings in the most effective way possible. Ensuring that everyone feels included in the conversation makes for a more collaborative environment. The biggest win for the design team was how much we were able to influence the conversation. Our research was invaluable to the direction of the project.

Hundreds of sticky notes were harmed during this workshop. In their sacrifice, we were able to define our vision, map out the first customer traffic plan, assign ownership areas, and get started. For the design team, some of our next steps included:

• Testing north star scenarios
• Following up on research questions that came out of the workshop
• Outlining an A/B test strategy with partners
• Putting together a post-FCT (first customer traffic) plan

More Work