Waypoint — Group Trip Planner

Waypoint helps friend groups plan trips together — everyone adds places, votes on them, and the group ends up with one shared itinerary instead of a group chat full of screenshots. About 1,200 groups had used it, mostly for trips under two weeks with four to eight people. People added plenty of places. Almost nobody converted a saved place into an actual plan. Itineraries stayed empty even on trips that were three days out.

Client

Waypoint

Role

Product Designer — led design end to end

Team

1 PM, 3 engineers, 1 researcher

Timeline

Feb – Jun 2026

Platforms

iOS, Android

Focus

Group decision-making, plan confidence, reducing chat overhead

airplanes window view of sky during golden hour

The Group Agreement View.

The challenge

Saving a place is easy. Deciding on it is not.

Every trip started the same way: someone made a list, everyone added ten places to it, and the list just sat there. There was no signal on what the group actually wanted — just a pile of restaurants and viewpoints with no sense of who was excited about what. So the real decision happened somewhere else: a group chat, at 11pm, the night before.


“We had forty saved places and zero plans. We ended up just wandering and hoping.”

— Beta user, six-person trip to Portugal

A lone tree on a grassy hill overlooking a pebble beach and mountains

The Group Agreement View.

The Process

Votes, not saves. A save says nothing about priority. We replaced the plain save button with a quick yes / maybe / no, so the list carried a signal from day one.

Overlap first. Nobody needs to see all forty places at once. We surfaced where the group actually agreed — the places with the most yeses — before anything else.

Sat in on real group chats. We timed how long it took three friend groups to settle on a single day’s plan by chat alone: 40 minutes, on average, for one day.

Killed the shared notes doc. It was the most-used workaround, and the thing everyone complained about. We built the itinerary to replace it, not sit next to it.

Solution

Group agreement view. Places sorted by how many people voted yes, with avatars showing exactly who’s in.

One-tap itinerary building. Drag an agreed-on place onto a day; Waypoint handles ordering and rough timing automatically.

Live status, not chat. Anyone can see who’s still deciding on what, without asking in the group chat.

Conflict flags. If two people vote opposite ways on a must-do, Waypoint surfaces it early instead of letting it surface the night before.


Outcome

Trips that reached a finished itinerary before departure went from 34% to 71% over the following quarter. The clearer signal: median time from first saved place to agreed plan dropped from nine days to three — the actual bottleneck we were designing for, since a list of saved places never booked anything on its own.

What I’d do differently. Voting worked well for groups of four to six. In groups of ten or more, a flat yes / maybe / no flattened into noise and some people stopped voting altogether. I’d want a lighter-weight signal for large groups in v2 instead of the same three-state vote for every group size.

Itineraries finished before departure

+37pts

Time from first save to agreed plan

-67%

We stopped scrolling through forty saved places at midnight. Waypoint just showed us where we already agreed.

portrait photography of man wearing black suit jacket

Priya Anand

Chief Innovation Officer

Let's connect

If the work above is the kind of thing you're looking for,
I'd like to hear about it.

Let's connect

If the work above is the kind of thing you're looking for,
I'd like to hear about it.

Let's connect

If the work above is the kind of thing you're looking for,
I'd like to hear about it.

Curiosity,
unpeeled.

Let's talk : )

SENIOR PRODUCT DESIGNER · BASED IN SAN FRANCISCO · PRODUCT DESIGN ·

Rhys

©

2026

All rights reserved.

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