PenMyPlan turns the group chat into a commitment mechanism: discover a deal, plan it with friends, vote, book, and split the cost in one app. I shaped the product strategy and designed the experience, then built it as a working iOS prototype and a narrated film for stakeholders.
Every group trip starts in a group chat. Ten friends, a hundred messages, a few hotel links nobody opens twice, and one organiser quietly doing all the work.
The decision happens somewhere no booking site can see. Polls live in one app, balances in another, rooms in a third, and the booking, if it happens at all, goes on one person's card. Most plans never leave the thread, and money is where friendships crack.
What if the place where a group decides were also the place where it books and pays?
PenMyPlan is one loop in one app: Discover, Plan, Decide, Book, Split. Deals are priced per person and for the whole crew. Each plan has its own chat, where deals, polls, bookings and expenses arrive as live cards. The group votes, the captain locks the winner, and PenMyPlan holds the price while each friend pays their own share. Expenses go in as the trip happens and settle up in the fewest transfers.
My role
Product strategy and design. Defined the product loop from the research, designed the iOS experience on the PMP Design Kit, built the working prototype in Expo / React Native, and directed the 2:20 stakeholder film with narration and an original score.
What made it hard
Plans die in the thread
Endless debate, no deadline and nobody with the authority to say "this one". The product had to give every conversation a next decision.
Planning is unpaid labour
Surveys put organisers at ten hours or more per trip, comparing options and chasing replies. Structure had to replace the chasing.
Money breaks friendships
One person fronting the whole booking is the fault line. Nobody should pay for anyone else, and nothing should be charged until the group commits.
The least-engaged friend
One friend who won't install an app stalls everyone. Voting and paying had to work from a link, inside WhatsApp or iMessage.
Questions we asked
How does a chat become a decision without feeling like a form?
Which voting method gets a group to yes, and can it explain itself?
How do you book for six people without anyone fronting the bill?
What does a friend who never installs the app still need to do?
01
Deals priced for the crew
Explore opens on hand-picked group deals across the UAE, India and beyond. Every price shows per person and for the whole crew, so everyone knows what it really costs, and every deal has one action: add it to a plan. A plan holds the dates, budget, itinerary and who's in. Friends join by link, contacts or QR code.
Explore and its group deals; a plan, and inviting the crew by link or from contacts.
02
A chat that moves forward
Each plan has its own chat, and deals, polls, bookings and expenses land in it as live cards, so the conversation always points at the next decision. Polls use approval voting: tick every option you'd happily do, with a "can't do" veto. Options re-rank live, and every ranking explains itself: who's in, and whose budget it fits. The captain locks the winner and the chat is told.
The plan chat with a live poll card; the vote re-ranking as the crew ticks options.
03
Book together, split fairly
PenMyPlan holds the price while the group pays. Each friend pays their own share with Apple Pay, a card, UPI or Tabby, and the booking confirms the moment the last share lands, with a clear "3 of 4 paid" and an automatic release if the hold runs out. On the trip, expenses go in as they happen and PenMyPlan settles everyone up in the fewest transfers.
Held, collecting, confirmed: paying a share with Apple Pay; settling up after the trip.
04
One accent on warm sand
The app speaks native iOS 26: large titles, a native segmented control, edge blur under navigation, sheets and spring-based micro-interactions. Colour is held back to one Ember accent on warm sand, from the Material 3-based PMP Design Kit in Figma. The prototype is Expo / React Native, so the same code runs on an iPhone and in a browser, in a phone frame on desktop.
The PenMyPlan mark, and the tonal palettes and light and dark roles of the PMP Design Kit.
05
Coming next: partners
Hotels, resorts and experience providers can't see small leisure groups forming, and room-block tools start at nine or ten rooms. A partner portal will show them anonymised group demand and let them send group offers that land directly inside the vote. Partners never see identities or the chat, and user data is never sold.
In motion
Outcomes
5steps in one loop, from deal to settle-up
3launch markets: the US, India and the UAE
4ways to pay a share: Apple Pay, cards, UPI and Tabby
A working prototype covering the full consumer loop, on iPhone and on the web from one codebase
A 2:20 narrated stakeholder film that tells the product story from the group chat to the partner portal
What I took away
Own the moment of decision. The booking follows whoever owns the place where the group says yes.
Make fairness visible. "3 of 4 paid" and an automatic release did more for trust than any copy could.
Design for the friend who never installs the app. A link that can vote and pay keeps the whole group moving.
