Before designing anything, I ran two small surveys (72 responses), mostly from self-hosted users. I was looking for two things: where teams might be willing to pay, and what the product was still missing.

Project managers and freelancers needed to share specific documents with external clients, but collaboration broke down when access extended outside the organization.

Team leaders needed control over visibility, permissions, and group access as teams scaled. Trust and coordination became organizational concerns rather than individual ones.

Both came down to the same gap:

Access control and management had become team-level needs, but the product still gave everyone the same access.

At first, we focused on where upgrade prompts should appear. But after reviewing user behavior, I noticed that upgrades were usually triggered when collaboration was blocked, not when someone happened to visit the pricing page. That shifted the design focus from the paywall itself to the collaboration flows that led people there.

As self-hosted teams grew, they needed a centralized way to manage users, workspaces, and access controls.