Situation

Ahead of Smartsheet’s IPO, we needed to drive feature adoption and user upgrades while sunsetting old account types.

Task

My team was responsible for designing in-app upsell patterns that boosted revenue without disrupting the user experience.

Action

I led stakeholder interviews, a design workshop, and four rounds of rapid usability testing to prototype and refine an upsell flow tied to a new feature. We ensured users quickly understood the value, their current plan, and upgrade options—or could easily dismiss it.

Result 

We tripled Business Plan upgrades in the first week, broke all previous sales records, and contributed to Smartsheet’s $150M IPO. The design is still in use seven years later.