
Amy Brumet
Increasing Annual Paid Plans with New Users
Whimsical is an all-in-one whiteboarding tool that helps people visualize and communicate their ideas faster and beautifully.
I helped optimize the freemium plan offering that increased annual plans and helped users explore their limitations.
Approach
Revenue had been plateauing for some time and Pro plans were stagnating with the freemium model. The hypothesis was that users who experience the full product would convert at higher rates and commit to longer-term plans. I supported the project including:
Wireframe concept exploration for trial benefits and communication
Collaboration with the Head of Marketing to refine the email touch-points
Design of upgrade paths for the various user roles
Support to design paths for edge cases and error handling with Engineering
UI, visual design and specifications for development
Outcomes
The final design included an in-app countdown, escalating upgrade modals throughout the trial period and main feature usage indicators. After an 8-week A/B testing, the reverse trial actually ended up underperforming, but revealed valuable insights:
Increased annual plan adoption of 57% vs 28% with control
Better retention for monthly subscriptions of 16.7% vs 28% churn
We didn't proceed with the reverse trial to replace the current freemium model, but instead opted for a freemium offer for a percentage off yearly plans during a 14-day window. This allowed for those who were unsure to get a deal, while listening to the data that showed our current freemium model was producing more revenue. This increased our yearly paid plans, but marginally increased our ARR.


