Problem
Match needed to grow subscription revenue within a high-intent marketplace where user trust and experience quality directly impact engagement and retention.
The challenge was designing monetization strategies that felt like a natural extension of user intent, rather than a disruption to it.
The core problem was balancing business goals with experience integrity in a way that preserved trust in the platform while still driving revenue.
Research/
Discovery
This reframed the problem from “how do we convert free users” to “how do we surface value at the exact moment of intent without breaking trust.”
We focused on free members as the highest leverage segment for improving subscription conversion. An audit showed they represented a large share of active users, but lacked clear pathways into paid value.
Data analysis revealed a core segment of men aged 40–50, many re-engaging with the app post-divorce. Across this group, intent was high, but conversion was constrained.
Survey data reinforced this tension. Users primarily subscribed to access core intent signals like likes and matches, but consistently cited price as the main barrier.
This reframed the opportunity from driving upgrades to aligning monetization with moments of intent, where perceived value was highest.
Likes in the stack
We explored several concepts and ultimately focused on surfacing the number of likes directly within the discover stack experience. The goal was to introduce a lightweight signal of demand that could increase intent without disrupting the browsing flow.
We aligned with engineering early to evaluate feasibility and implementation effort. This approach was selected because it delivered the strongest balance of user value, speed to ship, and technical simplicity within existing constraints.
Iteration
I began with wireframing some ideas to get the messaging right. When we decided what we wanted it to say, I made some quick mocks. We iterated on several options and brainstormed different touch points.
User flows
Solution
We introduced three non-intrusive monetization touchpoints designed to surface subscription value across different moments in the user journey.
A missed mutual nudge highlighted lost connection opportunities, a celebratory drawer surfaced likes and matches as positive reinforcement, and a post-free-picks modal introduced the upgrade prompt at a natural decision point.
Each was intentionally placed at different cadences to reinforce value without disrupting the core browsing experience, creating multiple context-aware opportunities to convert.
Installment biling
We implemented an installment billing system that allowed users to pay in biweekly installments. I worked within the development constraints to implement a design that clearly states when they will be charged.
Constraints
We wanted to be agile and work as fast as possible. My Product Manager and I had a brainstorming session and quickly drew up some wireframes and also looked at how other companies handle installment billing. We checked in with Dev to learn about our constraints. Unfortunately we can only do minimal changes to our existing billing page. However, we were able to update colors.
User flows
Outcomes
The missed mutual nudge was the strongest performer, driving a 4% increase in subscriptions, showing that timing and emotional context had a big impact on whether users chose to upgrade.
The installment plan initiative resulted in 21% of total subscribers and 40% of premium subscribers chose installment plans, along with a 3% lift in overall conversion and an 11% shift toward premium tiers.
What stood out most wasn’t just the numbers, but the pattern behind them. When monetization showed up in moments that felt aligned with user intent instead of interrupting it, people were more willing to engage and ultimately conve