TikTok
Savedhidden swimming spot in Hawaiʻi 🌴
Project Compass
The AI Agent for group trip planning.
The trip can finally make it out of the group chat.
Compass helps friends turn messy travel plans into trips that actually make it out of the group chat, all within iMessage.
Group trips rarely start with a plan.
They start with a conversation.
Ideas get tossed around in group chats, buried in screenshots, shared across links, and debated over dozens of messages before the trip ever becomes real.
TikTok
Instagram
Shared reeladding this beach to the list
reddit.comBest Oʻahu spots that aren’t tourist traps
Pinterest
PinnedHawaii ideas board · 28 saves
Hawaii budget.xlsxShared with 5 travelers
Hawaii itineraryLast edited 2 minutes ago
For my internship I was tasked with solving the question:
What could group trip planning look like if we brought AI into the picture?
The challenge isn’t finding inspiration.
It’s deciding what to do with it.
Travel inspiration is already everywhere, from TikTok and Instagram to Reddit, shared links, and screenshots.
The challenge is turning all of that into a plan everyone agrees on.
In numbers, the opportunities look like this:
Where three behaviors meet: messy group coordination, growing AI adoption, and social-first travel discovery.
say coordinating schedules is the #1 planning blocker in group trips.
of Gen Z and Millennials already use AI to plan trips.
turn to social platforms first for trip inspiration and destination ideas.
projected value of the Gen Z group-travel market by 2031.
Meeting the travelers where they are.
I chose iMessage because the barrier to entry is almost zero. If you have an iPhone, you already have iMessage.
That’s roughly 1 in 4 people globally. Compass joins the conversation, then hands off to Expedia when it’s time to plan or book.
Billions of AI conversations.
Zero new downloads.
The average person sends somewhere around 40 messages a day. If even a quarter of that volume shifts toward agents, that implies billions of messages to AI every single day, more AI conversations than every standalone chatbot app combined, happening inside a platform nobody has to download.
The user journey.
Six moments take the group from “we should go” to a trip everyone agrees on.
Save inspiration as you scroll
Compass turns shared TikToks and links into trip ideas the group can revisit.
Understand everyone’s preferences
Compass gathers each traveler’s dates, budget, and priorities privately.
Find stays that fit the group
Compass uses everyone’s preferences to surface hotels that work for the group.
Find common ground
Compass surfaces trade-offs and uses reactions and polls to move decisions forward.
Compare flights across travelers
Compass finds flight options around each traveler’s origin, timing, and budget.
Bring the trip together
Compass turns the group’s decisions into one shared Expedia Trip ready to book.
Onboarding
Compass starts with a private, lightweight intake that captures what each traveler needs, then moves directly into iMessage.
Advance through the prototype to see why each step is there.
See Compass in action.
See how Compass turns a group chat into a shared itinerary.
I brought the prototype to life in code.
I built the experience in HTML, CSS, and JavaScript to create realistic interactions and test how the product would actually behave.
- 01Find the core problem
Synthesized user research to understand where group trip planning breaks down and what the agent should actually solve.
- 02Decide where it should live
Compared existing planning behaviors and tools to find the lowest-friction place for an agent to join the group.
- 03Map the experience
Turned key planning moments into an end-to-end journey, from gathering preferences to resolving disagreements and making decisions.
- 04Prototype the interactions
Built the experience around realistic group conversations, interactive components, and the different states the agent needed to handle.
- 05Test and iterate
Put the prototype back in front of users, identified where the experience broke down, and refined the concept based on their feedback.
A few words from my mentors.
Feedback from the people who helped me sharpen the thinking, craft, and story behind Project Compass.
“Brenda, amazing, such incredible work and you've made HUGE progress since we started. I'm proud of what you did here, and I have no doubt your concepts are going to be surfaced in so much of our work here. Don't be surprised when you see how you inspired the org.”
“BRENDA!! Amazing job. Fantastic storytelling, honing in on the value propositions, and cue'ing up the moments that matter in the prototype. So proud of your prototype!”
“Great job with it! You have really delivered and used the time productive and I am happy to hear that you have found a supportive team and manager in your time here.”