Getting businesses to their first payroll, faster.

Businesses were dropping off before completing setup, and those who made it through weren't finishing the tasks needed to run payroll. The problem was structural: tasks were scattered across pages with no clear sense of what was required or what came next.

I partnered with PMM, engineering, and product to audit the full journey and redesign it around a key insight: a one-size-fits-all setup flow couldn't serve the range of businesses Square Payroll supported. We built a dynamic intake flow that collected business type, size, and compliance needs upfront — personalizing each employer's path and generating a setup checklist that served as a single source of truth for everything they needed to do. The framework proved flexible enough to expand beyond payroll, eventually becoming the foundation for the Square Staff setup experience.