Point.me had built something impressive under the hood: a search engine that crawled hundreds of sites and flight APIs to calculate the value of points, transfers, and pricing. But the product wasn't converting or keeping users.
I led a redesign across the information architecture, the free tier, and onboarding, with one goal in mind: making the product work for people who weren't already points experts.
Point.me helps people find and book flights with travel points, turning a famously confusing space into a guided experience. The technology was solid. The experience around it wasn't.
Growth was slowing, especially among people new to points and miles. Experts already understood the value of a strong search engine for award travel, so a paywall at the front door didn't bother them much. Everyone else needed a glimpse of what they could gain before handing over a credit card, and the product wasn't giving them one.
The structure of the product was quietly discouraging signups. Arriving on the homepage, people ran into a paywall almost immediately and landed on a pricing page that was both overwhelming and hard to understand. And for anyone not ready to book yet, there was little reason to come back. The people who needed time to warm up were the ones the product was losing.
That pointed to a shift in how we thought about users. Rather than treating everyone as ready to buy, we began to see a gradual journey from curious to highly motivated, and to design for each step along the way.
We moved Explore, a lighter version of the flight search, in front of signup. Curious visitors could now browse recently found flight deals and get a real feel for the product before deciding whether to create an account.
Instead of sending people to a dense plans page, I brought them into Explore, with working search and cached results. Paths to upgrade lived where interest was naturally highest: in the navigation, in banners, and inside the results themselves.
We introduced a short questionnaire that guided people toward a recommended plan or service based on their travel goals and how much they already knew about points. For travelers who wanted someone to handle it for them, it pointed straight to our concierge service, where an expert would find and book the trip on their behalf. It set honest expectations about the process and gave people something to look forward to before they'd done anything else in the product.
Map-based search, deal browsing, and travel inspiration gave people reasons to come back over time. That mattered as much for retention as for conversion. We focused on building a habit first, so that the moment someone chose to upgrade felt natural rather than pushed.
Signups doubled, and plan subscriptions rose by 4 to 10 percent.
Free-to-paid conversion improved by 3 to 5 percent, and people who upgraded used features up to 30 percent more.
Articles built around Explore doubled signups and became a reliable channel for new users.
We shifted our focus from expert travelers, a small and competitive group, to novices, a larger one that was underserved. Meeting people at their level from the first session replaced a single generic flow for everyone.
Explore gave people real reasons to stay, so the eventual upgrade felt earned.
We measured every change, which gave leadership the confidence to move ahead with a significant shift.
A path to concierge support meant no one felt stuck, even in a confusing domain.