PLUS Tutoring
TripPilot is an AI-powered travel planning platform designed to eliminate decision fatigue. By replacing fragmented research with an intelligent, adaptive itinerary and real-time conversational refinement, TripPilot turns 20 hours of trip planning into a 15-minute collaborative experience.
My role
Builder
Timeline
January to March 2026
My team
Just me!
Problem Space & Opportunity
Americans spend billions of hours planning trips every year.
Planning a trip can mean hours of searching across flights, hotels, maps, reviews, social media, and travel guides. I saw an opportunity to bring that fragmented process together and reduce the amount of work travelers had to do themselves.
2.4 billion
hours of excess trip-planning time each year*
Estimated annual U.S. impact based on my problem-sizing model.
Market Focus & Strategic Positioning
Not every traveler needed the same kind of help.
Trip planning looks very different depending on the traveler and the type of trip. I narrowed the market around the people who spent enough time planning for TripPilot to meaningfully reduce that work.
Everyone who travels
U.S. adults who take at least one trip per year
US Census Bureau, 2024
~260 million
Total Addressable Market
Leisure travelers
U.S. travelers who take trips for leisure (not work)
58% of total U.S. population (260M), US Travel Association, 2020
~150 million
Travelers visiting unfamiliar destinations
Leisure travelers who visit new cities or countries
Estimated annual U.S. impact based on my problem-sizing model.
~80 million
The target: high-value leisure planners
Travelers who take multi-day trips to unfamiliar destinations
Estimated annual U.S. impact based on my problem-sizing model.
~35 million
Competitive Landscape
Existing tools helped with pieces of the trip, but travelers still had to put everything together.
I compared the major ways people currently plan travel and found that most products focused on one part of the process: searching, booking, organizing, or generating recommendations.
Product Direction
That led me to focus TripPilot on the planning itself.
Instead of simply generating an itinerary, TripPilot would learn what someone wanted from their trip, create a plan around those preferences, and let them keep changing it through conversation.
Product Direction
I translated that strategy into 11 requirements for what TripPilot needed to do.
Understand the traveler
Preferences, budget, dates, constraints
Build the trip
Activities, timing, geography, reservations
Adapt the plan
Conversational changes and real-time refinement