Square

Automated Payroll, Tax Filings & Reporting

Square Payroll handles end-to-end payroll processing for W‑2 employees and 1099 contractors without extra charges per pay run. It automatically calculates wages, taxes, overtime, benefits deductions, and files all federal, state, and local taxes. The platform issues year-end W‑2s and 1099‑NECs on your behalf.

Timecards, Tips & Commissions

High-traffic businesses can benefit from Square Payroll’s seamless import of timecards, tips, and commissions directly from Square POS or the Team App. Over 10+ days of scheduling data is included, and labor cost reporting is available through the dashboard.

Unlimited Payroll Runs & Payment Options

There’s no limit on payroll frequency—you can run payroll weekly, bi-weekly, or on demand without incurring extra charges. Employees can be paid via next-day direct deposit, paper check, or instant deposit via Cash App, depending on plan and preference.

Automatic Payroll Option

With automatic payroll enabled, Square processes payroll automatically at 5 PM PT on the scheduled pay day, including imported hours, tips, and commissions. If needed, you have until 8 PM PT to cancel or edit the run.

Benefits & Benefits Deductions

Square offers payroll-integrated benefits such as health insurance, workers’ comp, and retirement savings. Employers control pre- and post-tax deductions, and employees can enroll via self-service.

Multistate Support & Compliance

Square Payroll supports multiple state tax jurisdictions, new hire reporting, wage garnishments, and ensures compliance across different regions, making it suitable for businesses operating in multiple locations.

Employee Self-Service Portal

Full and part-time team members can log into the Square Team App or web portal to view pay stubs, update tax withholdings, set direct deposit, and access 1099/S‑2 tax forms on demand.

Square Payroll is tightly woven into the larger Square ecosystem, which includes Square Point of Sale, Square for Retail, Square Timecards, and the Square Team App. This native integration allows seamless syncing of employee hours, tips, commissions, and time-off tracking without needing third-party tools.

However, Square Payroll is relatively limited when it comes to external integrations. It works directly with QuickBooks Online for syncing payroll data to your accounting records, but support for other major platforms—such as Xero, Google Workspace, or Microsoft 365—is missing. That can be a drawback for businesses looking to plug into a broader tech stack.

That said, within the Square ecosystem, add-on services like Cash App for instant payments, Square Checking, and Square Benefits (health insurance, retirement, workers’ comp) are available and integrate automatically. If you’re already using Square products, Payroll fits in with zero friction. But if you rely on a broader suite of non-Square tools, you may find the lack of third-party integrations limiting.

Square Payroll is designed to be simple, but the setup process can be time-consuming, especially for businesses migrating from another provider or starting fresh. Bookkeepers may find themselves entering past payroll records and employee information manually, which can be tedious. While there is an employee self-serve portal, it’s not always leveraged right away, and often only becomes useful just before the first payroll run.

Navigation is clean and intuitive. The platform covers the core functions well: employee setup, payroll runs, tax filing, and basic reports. Visually, it’s straightforward, functional but unpolished. For instance, the employee list feels more like a spreadsheet than a modern HR dashboard.

That said, core tasks are easy to execute. You can access and edit each employee’s profile, schedule payroll, and handle one-off changes like bonuses, reimbursements, or deductions. A standout feature is its integration with Square Timecards, which makes handling hourly wages automatic and hassle-free.

Where it lags is in customization and depth. Reporting is basic, with little built-in HR support or proactive compliance updates. Competing payroll platforms offer more advanced features in these areas.

Finally, Square Payroll is clearly part of a larger ecosystem. The sidebar prominently displays other Square products, encouraging users to integrate more tools. If you’re already using Square, that’s a win. It may feel limiting if you’re looking for a more standalone or expansive payroll suite.