2022Pitch
Making upgrades make sense
Hitting a paywall told you what you couldn't do, but not why Pro was worth paying for. As the solo designer on Pitch's Billing team, I worked with product and engineering to rethink that moment, creating a paywall system that's still used today.
ContextThe paywall wasn't doing enough
Our goal was to raise awareness of Pro's value and improve Starter to Pro conversion, targeting 50% weekly paywall impressions and a 20% click through rate. Upsells sent users straight to checkout without showing what they would unlock, and each entry point handled that moment differently, so the experience was inconsistent across the product.
A paywall wasn't just a place to ask users to upgrade. It was a chance to explain why. Someone exporting a presentation had a different reason to care about Pro than someone checking analytics or uploading a video, so the experience needed to reflect what they were already trying to do.
ProposalGive people a reason to upgrade
We added a learning step to the flow. The modal explained the value of Pro at the moment users hit a limit, giving them more context before moving to checkout. Below is one example: trying to export a PowerPoint without Pitch branding triggered an upgrade moment specific to that feature.
SystemFrom one paywall to many
Between July and September 2022, we rolled the approach out across more than eight features, from Presentation Analytics and PDF Export to Workspace Roles and Version History. The structure stayed consistent, while the entry point, messaging and visuals were tailored to the moment of friction. Each paywall could meet users in what they were already trying to do and make the case for Pro in context.
OutcomeStill running years later
The system shipped in 2022 and became Pitch's standard way of introducing Pro features. Years later, it's still running in the product.
That's the part I'm happiest with. Pitch has changed, new features have been added, and the team has kept building on the pattern rather than replacing it. What started as a clearer way to introduce Pro became a small piece of product infrastructure.