Trip Planner
PRODUCT DESIGN
Monetization funnel redesign that increased conversion through a redesigned onboarding funnel built around trust, personalization, and a clearer path to the paywall.
DOMAIN
Travel-tech
ROLE
Product designer
YEAR
April–August 2026
Product Context
Trip Planner is a travel platform where users get personalized itineraries built around their preferences, with trips curated by real travel experts. The audience: travelers who want a tailored plan without spending hours building it themselves.
The Problem
Users were dropping off between onboarding and paid conversion. Onboarding felt generic and didn't build confidence that the app would actually produce a personalized plan, and the paywall moment felt disconnected from what users had just gone through — arriving as a random feature carousel rather than a natural next step.
My Role & Team
I worked as Product Designer in a team of 5 — alongside a developer, the CEO, a marketing manager, and a frontend developer. I owned the audit, research synthesis, and redesign of the onboarding and paywall experience.
THE APPROACH
01
Discover
Audited the existing onboarding and paywall funnel using Mixpanel data and benchmark analysis to find where and why users were dropping off before converting.
02
Hypothesize
Turned research findings into four distinct, testable hypotheses — covering trial clarity, pain-point messaging, social proof, and investment framing.
03
Redesign
Rebuilt onboarding around the product's real differentiator (expert-curated trips) and redesigned each paywall variant to test a specific hypothesis, not a guess.
04
Test
Ran user testing on the new onboarding flow and A/B tested all four paywall hypotheses to see which actually moved conversion.
05
Ship
Shipped the winning onboarding flow and paywall variant, backed by evidence of what changed and why it worked.
06
Measure
Tracked onboarding and paywall conversion post-launch, confirming a +20% lift in onboarding and +8% on the winning paywall hypothesis.
Research Methods
Mixpanel funnel audit
Existing funnel audit
User testing
Benchmark analysis
Key Insights
Progress felt invisible: users were asked about their preferences, but the affirmation screens that followed were too generic to reflect it.
Users didn't feel the onboarding added value — generic questions gave no sense that the app would genuinely produce a personalized plan.
The app never introduced itself during onboarding — as a first-time experience, there was no moment showing users what the product could actually do.
The logic behind when the paywall appeared was arbitrary; onboarding never built toward a moment that justified showing it.
Onboarding and paywall felt like two disconnected funnels — onboarding was built around personalizing your itinerary, while the paywall showed only a generic feature carousel at the end.
Design decisions
Introduce the expert, early. Trip Planner's core competitive advantage — that every trip is curated by a real travel expert — wasn't used anywhere in onboarding. I proposed assigning an expert to the trip based on the user's destination selection, then walking the user through onboarding alongside that expert to build trust from the first screen.
Design decisions
Ask sharper questions, show the outcome immediately. Based on user interviews, I mapped the specific inputs people actually consider before building an itinerary (hotel preference, pace, who's traveling, trip type) and added these directly to onboarding — each paired with an immediate, visible outcome: selecting a hotel preference showed matching hotels added to the plan in real time; selecting a pace showed how the day's schedule changed live.
Design decisions
Rebuild the paywall around tested hypotheses, not guesses. Since the team had already tested some paywall variants, I catalogued the specific problems observed and turned each into a distinct, testable hypothesis.
Hypothesis #1
Users weren't converting because the free trial mechanics were unclear — split the paywall into a clear explanation of how the trial works, followed by plan selection.
Hypothesis #2
Copy on the paywall didn't reflect the user's real pain — spending hours planning without knowing if they're doing it right. Rewrote the paywall to lead with that pain point directly, and simplified to one recommended plan (with all plans available a tap away) to reduce decision paralysis at the moment of conversion.
Hypothesis #3
As an early-stage startup without strong brand credibility, the paywall lacked social proof. Reframed the headline and copy around community and belonging ("join the club of Pro travelers") and layered in traveler avatars, ratings, and trip reviews — testing whether feeling part of a trusted community of travelers increases confidence and conversion more than a feature-led message.
Hypothesis #4
Users' biggest hesitation was spending money on an app they might not use — reframed the subscription as an investment by showing, as a feature, how much the user stands to save on their actual trip cost.
THE OUTCOME
Onboarding Conversion
Paywall Conversion
A NOTE FROM THE DESIGNER
The best onboarding doesn't ask users to trust the product blindly — it shows them, immediately, what they're getting.