2019 · UX · UI

Tailor-Made Trips: Greater Flexibility for Anywhr's Travellers

Anywhr's new direction in trip planning




Product Manager - Felix Tan, Engineering - Rahul Gupta & Dhruv Jain


1.5 months

After running a 5-day design sprint company stakeholders, we validated that expanding the product in terms of the type of travel experience Anywhr provides is worth pursuing to expand our market reach. We started offering ‘Tailor-Made’ trips as a counterpart to the original ‘Surprise’ trips. Travellers can opt for having more control over their travel itinerary with the Trip Curator’s help in planning and booking their trip.

Quickly gaining insights with an chatbot

As we knew that the engineers needed a longer time to complete the new user flow on the web app, we decided to launch the MVP as an Intercom bot as this was the fastest way (that required the least engineering effort and time) we could gain insights on how to structure the operations for planning Tailor-Made trips to inform design decisions. The Intercom bot was easily modifiable by the Trip Curators as they could easily refine and prioritise the questions they ask travellers.

This replaced the How It Works section on the homepage to reflect Anywhr's new offering.
At the points where the user would have started the trip customisation user flow, this dialog now appears.

Educating users on the new product option

As most users would have already known Anywhr as a trip planning company specialising in surprise trips and less-known destinations, we need to introduce the Tailor-Made trip to users. I identified places in the web app and points in the original user flows where instead of heading to the original Trip Customisation user flow, there would be an interface that contrasted the two types of trips the user can choose from.

Simplified user flows showing the change after implementing the Tailor-Made trip user flows.

Integrating the new user flows with the existing system

Together with the product manager, I brainstormed on integrating this new user flow into the current trip customisation user flow, but it was too different in the types of information/data obtained. Feedback from engineering also supported keeping the two flows separate as it will take much more effort to change the existing database structure for the existing Surprise Trip to accommodate the Tailor-Made Trip if they were to be recorded in a single database table.

Reducing users' time and effort to get their trip planned

With the feedback from Trip Curators who handled the trip planning operations since the implementation of the MVP, it was easy to rate the importance of each question. As it was logistically difficult to plan a large number of trips, Trip Curators needed to prioritise the trips based on budget and travel dates while users often gave ambiguous answers to questions such as their travel dates and destination. Such ambiguity always led to more back-and-forth conversation which increases the probability of the user losing interest in Anywhr’s service as time goes on. This indicated a need to reduce open-ended answers by providing categorised options.

From left to right: the earliest iteration to final design. Through multiple iterations, I realised that users don't need the search bar as they wouldn't know what options there were. All users instinctively scrolled down to view the available options.

Iteratively improving the usability of questions for users to provide concise yet accurate trip preferences

As the intended user flow directly replaced the parts where the Intercom bot was implemented, I designed usability tests that focused on tasks within the trip request user flow such as changing from specific trip dates to a relative travel period and the indication of specific activity interests.

On the left, the button that leads to the page for relative travel dates is too close to the illustration at the bottom hence most users missed it during usability tests. The button interface on the right worked much better.

Here is one of the iterations that was used for user testing. For the user tests, users were given a specific context for which they had to complete a Trip Request for.

Key screens from final UI design


Test thoroughly to make sure there are no broken flows before launch. Trying to hack a third-party app into the MVP user flow met with more technical challenges than initially thought. Though the two engineers and I managed to fix the bot launching issues in the end, there was close to a week that the Tailor-made Trip was supposedly launched, with the homepage and How it Works page already updated to reflect that.

With that being said, a communicative and collaborative team makes a quick resolution of issues. I have only known the engineers for a short amount of time but they were open to collaboration and willing to go the extra mile to make things work.

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