Dropbox Cancellation Flow

Context

Dropbox needed to rethink the cancellation experience. The existing flow prioritized friction over clarity: a growing internal concern, and a source of measurable damage to long-term trust with users who came back. I led the redesign with a mandate to balance retention goals against genuine respect for the person on the other side of the screen.

Approach

The core reframe: cancellation is a customer service moment, not a retention battle. People who cancel and feel treated well come back at meaningfully higher rates than people who cancel and feel manipulated. I built the flow around that thesis and stress-tested every screen against a single question: would I be embarrassed if a friend saw this?

Note

This case study includes confidential metrics and internal strategy that I can’t share publicly. If you’d like to walk through the work in detail (the retention lift, the specific patterns we killed, the framework I used to negotiate with growth stakeholders), reach out and I’ll happily set up a call.