Information Architecture · TripIt
TripIt Information Architecture Overhaul
A systems-level diagnosis, a design-led initiative, and a four-year push to fix a structure the product had outgrown.
A systems problem — diagnosing why features weren't landing, building the case through two separate initiatives across four years, and sustaining that push through team dissolution and a period as the sole designer.
The problem
TripIt launched in 2008 with 2 features. By 2025 it had 20. The structure underneath never changed.
From 2008 to 2025, one structure: Trip list → Trip summary → Plan details.
What it was built for: viewing a trip you’d already booked.
What TripIt had become: a travel companion with features covering every phase of the journey — research, booking, pre-trip prep, in-transit, post-trip.
Those features had nowhere natural to live. So they were shoehorned into a structure that wasn’t built for them. The results were predictable:
- Planning tools accessible only after a trip was already created
- Safety scores you could check only after booking the hotel they might have warned you away from
- Features the product had shipped that almost no one found, with engagement numbers in the low single digits to prove it
Each one looked like a discoverability problem. Taken together, they were a structural one.
A design-led initiative (2021)
This became the first design-led initiative on TripIt’s roadmap, and I led it.
At the time, roadmap work started in Product or Engineering, never Design. To get the IA problem addressed, the design team proposed it ourselves. That framing was new on its own.
Team
- Me (Senior) — the initiative, plus the design explorations and iterations
- Kyle (Research) — user-journey research and internal card sorts to test a new structure
- Steve (Principal) — an IA workshop with cross-functional stakeholders to turn the research into How Might We statements
- Kaitlyn (Intern) — the Tools tab, which she owned and presented herself, with me as her mentor
What we proposed
A structure organized around the traveler’s journey instead of a list of a group of features.
How it landed
Product and engineering were not convinced. The “systematic problem” framing was largely still seen as a design team concern and not one that seemed to need a restructure.
What we won
The removal of the catch-all “More” tab replaced with a dedicated Account tab, and a global search bar shipped to iOS. The rest of the structure waited.
The 2024 prototype
Priorities shifted, but I continued to iterate on the side. In 2024 I saw the opportunity to resurface the restructure, this time to address an immediate need: another wave of new features with no entry points in the old structure.
This time I came back with a working prototype instead of a proposal.
The new structure
- Travel — the itinerary hub, now with a global search bar and a segmented Itinerary / Calendar / Tools view inside each trip
- Plan — a dedicated pre-trip tab: safety scores, travel guidance, saved places, destination suggestions, all available before a booking exists
- Account — the full realization of the partial win from 2021, a proper home for everything user-specific
What changed for each named problem
- Planning tools now lived on the Plan tab, accessible before a trip had been created, and no longer locked behind a pre-existing booking
- Safety scores and Travel Guidance surfaced contextually, matched to the destination already in the itinerary
- The trip view split into dedicated tabs — Itinerary, Calendar, and Tools — separating the timeline from trip-level features and content not directly tied to it. Features previously buried in overflow menus now had a logical, visible home inside the trip itself
- Calendar, one of the most-requested features in five-plus years of customer feedback, had a real home in the trip view
How it landed
This time there was no arguing against it. Betsy (Director of Product) signed off on beginning formal discovery. Justin (PM) came on as partner. That discovery phase had just started when the layoffs happened.
What this demonstrates
The entire US team, myself included, were laid off before we could move into product discovery. But the problems had finally been acknowledged and the work was ready to go.
The four existing case studies on this site show how I work a specific problem: a feature, a flow, a stakeholder constraint. This one shows something different — how I work a system. Specifically:
- Identifying a structural problem that everyone else was solving one symptom at a time
- Sustaining a diagnosis across four years, a team that dissolved, and a period of running the entire design function alone
- Building the case iteratively — from a proposal, to a prototype, to a version compelling enough to earn a director’s sign-off on a problem that had spent years being dismissed as a design-team concern
- Shipping partial wins along the way — the Account tab and a global search bar both made it into the product from the 2021 initiative, the search bar to iOS
“Kat, when we became part of the same team, I told you I respected your work and was looking forward to partnering with you. You lived up to every bit of what I was hoping for in a partnership. I really admired how well you communicate, how thoughtful your designs were, how much you listened and included different perspectives, and how well you navigated strong opinions. We had so many plans for the future and we were just about to hit our stride. I wish you all the best in your career and will keep in touch. We are TripIt family.”
Justin Lee
Principal Technical Product Manager — TripIt
