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Generative research // Product design // Interviews // Card sorting // Mobile & web

About this project:

People use Airbnb to book multiple items for a single trip. The current checkout process is linear and repetitive; users have to repeat multiple steps to complete their purchases. Our goal is to design a product that enables users to easily pay for their end-to-end trip in one seamless experience.


People planning a trip book and pay for multiple items, such as lodging, transportation, activities, amenities, and extra fees for things like parking or services. A common type of multi-item purchases on Airbnb are multi-leg trips, which are consecutive trips booked by the same user where the checkout date of one trip coincides with the check-in date of the next.


Airbnb currently allows users to purchase multiple items for a single trip, but the checkout process is segmented. As a UX researcher for the Payments team, I sought to explore how to unify the experience for purchasing multiple items. One possible suggestion from the team was a "shopping cart."

Travelling in America
Multi-leg trips account for 30% of total Airbnb bookings, yet the current checkout process is linear, repetitive, and segmented. 
Screen Shot 2020-04-19 at 3.32.01 PM.png

Stay #1

Enter dates, details and preferences

Search & decide


Stay #2

Enter dates, details and preferences

Search & decide


Stay #3

Enter dates, details and preferences

Search & decide


Repeat process for next Stay


Repeat process for next Stay


Repeat process for next Stay



This project was a large scale cross-functional effort with overarching long term goals to streamline the user experience for trip planning and purchasing. We reminded ourselves of the big picture goals that guided each subsequent stage of research and design. My role was to conduct generative research that provided direction for the team.

Our goal is to design a product that enables users to easily book their end-to-end trip in one seamless experience.
Person Rolling Suitcase in Airport

The first few phases of research were designed to understand users and non-users current planning processes, pain points, and experiences. 

Planning Travels


How do trip planners currently book multiple trip components, such as lodging, flights, activities, and extras? What tools and strategies do they use?


What is the timeline of booking multiple items? Are people booking in one sitting or over time?


How do trip planners organize and prioritize the components of their trip? Are there opportunities for multi-item bundles?


What are the frustrations in existing booking processes? What opportunities exist to make experiences more enjoyable? In an ideal world, how might users prefer to book multiple purchases?

PHASE 1: Remote interviews with Airbnb users

During this first phase of research, I interviewed people who had recently planned a multi-leg trip. Purposely, I recruited participants who had booked the majority of their trip but had not yet traveled since I wanted the planning experience to be fresh in their minds. This allowed me to dive deep into their cognitive processes associated with planning and paying. We chatted about their planning timeline, the rationale behind various payment choices, obstacles and frustrations, and any upcoming planned purchases.

Screen Shot 2020-04-15 at 7.45.02 PM.png

Participant criteria:

  • Airbnb users that booked a multi-leg trip within the past 3 months​

  • Multi-leg trip includes at least 3 separate stays

  • Booked in the past but not yet traveled (i.e., travel dates in future)

  • Individuals primarily responsible for trip planning

  • ​Variety of geographic areas and methods of transportation

Pre-interview homework:

Before the interview, participants were asked to visually represent the process of planning and booking their trip. 

PHASE 2: In-person interviews with card sorting of trip purchases

During this second phase of research, my team wanted to hone in on how people organize and unify the individual purchases they make for each trip. I led Airbnb and non-Airbnb users through a card sorting task where they freely arranged purchases made for their trip. We also discussed how they might "bundle" purchases together in an ideal world. Enlightening and common themes arose that directly informed the team strategy moving forward. 

Participant criteria:

  • Individuals who planned and took a trip within the past 6 months

  • A mix of multi-leg trip and single-leg trips

  • Individuals primarily responsibility for planning

  • ​Variety of geographic areas, methods of transportation, and trip purposes

  • Variety of demographic representation considering education, income, gender

  • Interviews conducted in Chicago & Vancouver

Pre-interview homework:

Participants brainstormed and brought a list of all the purchases made for the trip, including before during and after traveling. 

card sort demo.jpg
PHASE 3: Competitive analysis of e-commerce and online travel sites

An ongoing phase of research throughout this endeavor was to gain insights into what methods online e-commerce and travel sites have in place to support multiple items checkout, such as shopping carts, progress saving, and flexible checkout. While this search focused on travel purchases, I also expanded beyond the travel domain to see what we could learn from other products and services.


After all three phases of initial research, we spent the final day in Vancouver during a full team debrief and brainstorm session. We had more ideas than could fit on the wall (and as a bonus, we found a pug named Doug)!

team workshop.jpg
team brainstorm.jpg

As this is an ongoing project, I can't share all the nitty gritty details, but here are a few high level insights that led to product recommendations.

Users booked their trips incrementally, purchasing major items such as flights, rentals, and hotels, before taking their time (weeks, months) to book the rest. Users were rarely ready to buy activities until much later.

How long does it take to plan a trip from start to finish? 

Booking a full trip took anywhere from 1 day to 8 months. Most participants took about a month to plan and book the whole trip, from first home/flight to final home or transportation booked.

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1 day

8 months

Average: 1 month


We don’t have any activities booked yet. I could have a list of things but we’ll probably wait until the day or two before to see what the weather will be like.

Users enjoyed the process of building their trip together piece-by-piece.

“The happiest you are during a vacation is during the planning phase. And I really enjoy planning all the things.”

Happy Coffee
Users incurred multiple costs from different reservations which led to confusion in managing upcoming payments. 

I get multiple confirmation emails with every booking. It’s really hard to keep track of which one has the payment due.

Participants purchased items individually but needed to create their own tools to stitch the pieces of their trip together, such as spreadsheets, maps, and receipt books.

Users want to be able to pick up where they left off, but right now they can't.

Users go through the checkout process to see final dates, details, and prices, but abandon this page when they aren't ready to buy. Over 12% of users come back and finish checkout within the same day, but all steps must be repeated.

Provide flexible options for users to pay for items on their own terms by purchasing them together in one moment, or individually over time.
Provide transparency with a payments dashboard so users can track and control upcoming payments for their trip.
Assure users that we remember their journey by auto saving their progress and enabling them to seamlessly resume upon return. 

A key takeaway from this work is that purchasing travel is a unique process that doesn't fit the mold of traditional e-commerce experiences. Thus, a typical "shopping cart" won't do the trick, especially considering the Airbnb user base plans a diverse variety of trips. As this was an early-stage generative research project (and is still ongoing), our team created three themes to guide product development moving forward. 



Provide flexibility that enables users to make purchases when and how they want



Returning to pay is streamlined and users can pick up where they left off



Unify individual purchases within the broader context of the holistic trip

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