I gathered 1 product manager and 5 engineers remotely in Figjam to convene on the infrastructure around free vs. paid plans. By facilitating a collaborative brainstorming session, I was able to gather the right people in the room with the right knowledge to generate ideas around some of the main problems we were solving for:

In both our onboarding checklist and in the product switcher menu, I included a general jumping off point to gauge user interest. This offers the user the opportunity to learn more about the most popular features they would receive access to in a free, 30-day trial. The primary action they have here is to start a trial for 30 days.

In addition to a general upsell, I proposed offering upgrade access points alongside various features. In this way, we are upselling the customer according to their interest in a given feature. This accomplished two things: 
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1. It tailors the upsell to the customer interests
2. It does not lock the free customer out from seeing the breadth of available features in paid plans.

In this, I focused on transparency and communication by highlighting these features with a paid plan tag and calling attention to the paid plan. These tags solved the below problem:

How might we communicate to the user at different points in their trial journey which features belong to which plans?

To better surface the workspace’s data usage in relation to the data limits, we decided to utilize the product switcher menu.  Given that there are data limits around board cards, messages, file storage, and integrations, we made this section on the menu dynamic to only reflect the limit that the workspace was closest to hitting. We used color to communicate how close the workspace was to hitting the limit. This design was just one piece of the solution that solved for the problem:

How might we communicate the workspace’s data limits to the user?