Rebuilding Point.me's Experience for Reward Travel Novices

Context & Problem

Point.me helps people find and book flights using travel points, turning a notoriously confusing space into something searchable. The technology behind it was solid: a search engine crawling hundreds of sites and flight APIs to calculate points value, transfers, and pricing. The experience wrapped around it wasn't.

The core flow of the product and Information Architecture (IA) was quietly preventing signups: when you landed on the homepage, you hit a paywall almost immediately, ending up on a pricing page that was somehow both overwhelming and difficult to comprehend. The free tier gave people little reason to come back before they were ready to book, losing the users who needed time to warm up. And the booking flow assumed expertise, information-dense screens that made sense to a seasoned points traveler, but lost everyone else.

None of these problems existed in isolation. A confusing IA meant most people left before seeing the product’s value. A thin free tier meant the ones who did had no reason to stay. And an expert-level booking flow meant even engaged novice users could fall off right before converting.