Helping sellers set up and run their first payroll compliantly
The problem
New Payroll sellers at Square struggled to complete setup. The existing flow presented only three generic steps, leaving out critical configuration tasks like adding employees, setting pay schedules, and enabling benefits.
This incomplete experience caused confusion, high drop-off rates, and negative feedback. Only 16% of sellers who started setup successfully sent their first pay run. Sellers needed a clear, guided experience to help them set up correctly and get “payroll-ready” without outside help.
What we built
We created the Staff + Payroll Setup Guide — a task-based onboarding experience that personalizes setup based on each seller’s business type, workforce, and compliance requirements.
The guide dynamically adjusts based on inputs like whether the seller pays contractors or W-2 employees, operates in multiple states, or has run payroll before. This ensures every seller sees the right set of tasks for their situation.
Turning setup into a guided experience.
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Tailored setup from the start
Intake questions helped us understand each seller’s business — from prior payroll experience to compliance needs and deadlines — allowing us to personalize their setup flow and surface relevant upsells.
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Keep momentum going
After completing one task, sellers were automatically guided to the next, supported by a progress indicator that showed how far they’d come and what was left to do.
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Deadlines that drive action
Critical tasks were prioritized with clear deadlines to create urgency and ensure we captured the right information for tax filing and compliance.
The impact
25% increase in setup completion
Setup completion rose from 16% to just over 30%, and 20% more sellers ran their first pay run after setup. Support calls for tax filing dropped by 12%, helping sellers get payroll-ready faster and with fewer errors.