Interview Questions › Product Design

Design a collaborative travel itinerary and expense splitting app for friend groups

Design an all-in-one collaborative trip planning, interactive itinerary, and group expense splitting application for groups of 4–10 friends organizing vacations together.

Context

Group trips are notoriously stressful, managed across chaotic 400-message WhatsApp group chats, disconnected Google Docs itineraries, and bitter arguments over Splitwise receipts weeks later.

Clarifying questions to ask first

• Does the app handle in-app bookings for tours and flights or organize external confirmations? (Syncs external email confirmations + links to direct booking).
• How are uneven expense splits handled? (Itemized receipt assignment).

How to approach it

1. Group Travel Roles: The "Trip Leader" (overburdened organizer doing all research), The "Easy-Going Participant" (wants to vote on dinner spots without making spreadsheets), The "Budget-Conscious Friend"
2. Design Unified Group Planning Workflow:
3. 1. Collaborative Interactive Map-Itinerary (Drop restaurant/activity pins onto an interactive day-by-day map that auto-clusters nearby attractions to minimize transit time)
4. 2. Democratic "Group Polls & Vibe Voting" (Vote on Airbnb options or activities with instant consensus rankings)
5. 3. Automatic Multi-Currency Expense Splitting with Receipt OCR (Snap receipt photo -> AI assigns drinks to Alex and pasta to Maya -> auto-settles debt via Venmo/Revolut)
6. 4. Shared Flight & Hotel Booking Confirmation Hub

Framework: Group Travel Chaos & Role Analysis -> Collaborative Itinerary & Map Engine -> Democratic Voting UX -> Integrated Expense Splitting -> Retention & NPS Metrics

Sample answer

• Organizing itineraries by geographical map clusters prevents wasting 3 hours crisscrossing a city
• Combining itinerary planning with real-time expense splitting in one app eliminates the need for 4 separate apps

1. MVP: Real-time multiplayer map itinerary, group voting polls, email confirmation auto-import, and receipt scanning with 1-tap Venmo/Splitwise balance settlement

Executive design: A collaborative group travel planner uniting real-time map-based itinerary building, democratic group activity voting, and automated itemized receipt expense splitting.

What interviewers look for

• Group Collaboration & Consensus Mechanics
• Map-Clustered Itinerary Optimization
• Receipt OCR & Multi-Currency Expense Settlement
• Friction Reduction for Group Organizer