A confirmation reaches TripIt one of two ways: you forward it to plans@tripit.com, or Inbox Sync scans your inbox and finds it for you. From there it’s parsed by DataMapper, TripIt’s internal parser, with an AI fallback for when DataMapper can’t read it. That fallback was TripIt’s first AI feature, which meant designing the flow that explained it, the setting that controlled it, and the way an AI-parsed plan got marked as such. The finished plan drops into an existing trip if the dates fit, or starts a new one. The trip itself is structured for how people actually travel: a scannable trip list, a trip summary built for quick glances on the go, and full plan details underneath for the travelers who want them.

Planning and booking. Neighborhood safety scores (women’s safety, LGBTQ safety, and more) to inform where you stay. Destination guidance like visa and vaccination requirements.

Before the trip. Fare tracker, which flagged when a price drop made you eligible for a refund and regularly put money back in people’s pockets. Seat maps and seat tracker, aimed at getting you out of the middle seat. Check-in reminders that surfaced your confirmation and flight numbers the moment check-in opened.

During the trip. Real-time flight alerts, the highest-value feature in the product. And the itinerary itself, which stayed the single most accurate record of your trip because it built itself from your actual bookings.

Outside of travel. Point tracker, for loyalty balances across programs in one place. Trip cost summaries, pulled from booking data to make post-trip expensing less painful.

The old site had aged into a liability, so the decision was made to replace it entirely rather than keep patching it. That meant redesigning every core flow and every feature for the new web, not porting the old ones over. Mobile stayed largely as it was, picking up only the improvements we decided were worth carrying across, which I was also in charge of designing. Four years is a long time for a rebuild, and a good part of that was the product weathering a long stretch of shifting priorities and team restructures.