Pilot | Travel Sidekick
Pilot | Travel Sidekick

Pilot | Travel Sidekick

Type : Start-Up

Timeline : Aug 2020 - Ongoing

Role : Product Design Lead

Responsibilities : UX + UI

Stage : Shipped 🚢

my role, our story

Pilot is a pre-seed start-up which I joined as a founding team member. I work alongside another product designer as well as the CEO, PM's, and four Devs.

We're a scrappy team made up almost entirely of students. Starting out as a product design intern, my role quickly became all encompassing. I was able to design much of the product as well as the main branding elements, website, and help contribute to the product roadmap.

Our alpha came together in a quick 6 months and is currently in private testing.

pilot : a collaborative trip planner

1. invite your friends using any social app

2. build an itinerary together-in real time

3. travel with all your plans in one place


If you've ever planned a trip with friends, chances are your tabs looked like this:


We're building a collaborative trip planner so they look more like this:


I'll be walking you through my work on the social components of the web app


so, how do you plan a trip with friends?

Most people chat about it with friends until one of them starts planning. Participants we talked with reported talking about trips with lots of friends but the majority fall through and never happen. Success rate is less than 50%

They share trip destinations via social media platforms like Instagram and Pinterest. These are helpful because the visuals help inspire action and give the planners a starting point.

Ex. "Let's go to this waterfall" and then they plan around the waterfall visit.

Pain Points

  1. Travellers have trouble finding friends who are willing to travel with them. Friends often want to travel to different destinations.
  2. They are unsatisfied with their ability to find/discover destinations which are suitable for them.
  3. Visual inspiration is separated from their planning and therefore the original idea gets lost.
  4. The activities attracting people to a destination differ from that of their friends. Difficulty agreeing on which activities to plan for.


"I'm too scared to travel on my own and don't have anyone to go with" - Megan Ngyuen

How might we?

Facilitate, Encourage and Spark group travel.
Bring friends together with shared travel ideas.

Ok ok not so fast there buddy, first we need to understand where we stand as a business.

market vibe check



75% of travellers say their travel budget is the same or greater than it was in 2019

70% of them plan to go on an international trip when travel restrictions are lifted

big picture considerations

As we were designing a product from scratch, there were considerations to be made. If we executed these correctly, it could lead to the success of the product.

network effects

The ability for the product to become more valuable with the addition of each new user. It's the key element which every social product utilizes to be successful. How we could produce network effects was a massive consideration.


What value do users bring to other users on the platform? Why should they be excited for more users to join?

market gaps

The travel industry is big and scary, in the US & Canada it has a TAM* of 501 Billion dollars! That's huge, but it's currently being taken up mostly by a few large players. Lucky for us, large players move slowly and leave gaps. That's exactly what we're looking for.

* total addressable market


Where do the current players leave opportunity for improvement? What features do users want but aren't getting?


Unbundling is the process in which different business sectors are separated and become independent marketplaces. Due to the internet, the travel industry has been unbundling for decades. What used to be done by one travel agent has turned into 10+ different service providers.

Flights ➡️ Google Flights / Hopper

Hotels ➡️ Hotels.com / Trivago / Etc

Activities ➡️ TripAdvisor / Eventbrite

Rentals ➡️ Airbnb / VRBO / Etc

We talked to travellers and they're unsure on how to get the best deal or what new website to use. There's too much choice! We believe it's time for a re-bundle.


Which features make sense to be bundled vs unbundled? Where do we find the middle ground between enough variety and too many options?

Great, now we can get to the fun stuff ↓

inherited designs
inherited designs

my task

Design a simple user interface which allowed users to see an overview of their profile. While maintaining a cohesive user experience with the rest of the product.

I decided to follow a "classic" profile structure to reduce any extra strain on the user.



This is a users personal travel profile. A place to curate travel ideas, share them with friends, and also discover new travel opportunities.

impact metrics

Activation and Engagement

Do desired outcomes occur within 30 days of sign up?

  • Planned a minimum of one trip
  • Added minimum 4 wishlist items
  • Added minimum 1 friend
  • Sent minimum 4 messages (when a friend exists)

If no, why not?:


Any trips that the user has made or been a part of will live here. These trips can be made visible to the users friends in order for them to collaborate or replicate.


This is the users bucket list. Any travel ideas or interesting finds can live here and then be created into a trip when they're ready! Also visible to the users friends who may like or save the idea.


Any friends the user has will be listed here. The friends list can be sorted and filtered by trips they may have gone on together.

behind the scenes process


Reducing Redundancies

User testing revealed several redundancies. For example, multiple "edit" functionalities caused confusion for users. By combining functionality where possible I was able to simplify the UX.


Learned Behaviours

I wanted to make use of the learned behaviours most users carry from other social platforms. One of these being the common use of personalization in a profile. For this reason I added features such as cover photo, bio, and social tags.


Dev Challenges

Early stage start-up = Limited resources

Our designs had to be optimized for both user experience but also development speed. Particularly the modular wishlist proved to be a challenge for the dev team. Therefore it was swapped to a fixed design.

Revealing Functionality

Discovering the fine balance between "simple" and "hidden" proved to be difficult. I discovered certain functionalities needed to be clearly visible in order for users to understand the nature of the feature.

Specifically, having the public/private icon and share icon helped users imagine how they would use the wishlist feature.


fail, learn, repeat

After releasing the alpha prototype and receiving feedback from users, we recognized there was no need for a side nav. It was hogging prime real estate while adding minimal value.

The top nav was our solution.

so what else did I design?

share module


Users have created a trip itinerary and they want to share it with a friend! Their friend will either be joining in on this trip or they'll be duplicating the itinerary to replicate on their own.

impact metrics


Measure change in desired outcome after implementation

  • What's the average trip invites sent to non-users per user?
  • What's the average trip invites sent in-between users?


an image and short description of the trip itinerary you're sharing


select who to send it to by browsing your friends on the platform or inviting them


friends aren't on pilot yet? no problem, send a link via your preferred method



In order to plan a trip you need plenty of communication. The built in chat allows users to discuss and decide while they build the trip.


Every trip plan has an integrated group chat, serving as the communication hub for that trip. Users can also chat in individual chats separate from the trip plan.

design challenge

The messenger was difficult to implement on top of an already busy layout.

After many iterations I decided to incorporate the chat to the existing blade architecture. Ask me why!



push it

Direct integration with the trip planner was a highly requested feature. That's why we designed a push feature which allows users to push ideas from chat directly into their itinerary or notes.



A design adjustment towards the implementation of a top nav caused us to reconsider the chat placement. Having reviewed the options we redesigned it to be embedded in the top nav bar.

The chat being located on the top nav increased user accessibility to the feature. Allowing users to collaborate independent of where they were on the app.

impact metrics (currently being tested)


The Goal

NPS above 50

How is it measured?

“Would you recommend Pilot to a friend?” scored out of 10

  • The percentage of those who answer 9 and 10, is subtracted by the percentage of those who answer 6 or below.

The 40% test

  • How would you feel if you could no longer use our product?
    • Very disappointed
    • Somewhat disappointed
    • Not disappointed (it really isn’t that useful)
  • Goal is to have 40% say “very disappointed”


The Goal

Users go from "sign-up" to "activated" in one day.

Sign-up: Email confirmation.

Activated: Minimum one trip planned with five inputs

How is it measured?

1, 3, 7, 30 day retention (signup to activated)


The Goal

Users access the app twice per day (while travelling)

How is it measured?

Measuring the amount of times the user is accessing the app while they are travelling.

Quantifying the use of mobile vs web app while travelling by measuring usage across platforms.


The Goal

Users plan an average of one trip per 90 days.

How is it measured?

Measuring the average amount of time between trips planned.

Measuring the down time between travel and the next trip being planned.

Thank you for reading 🙂