Square - Payroll — Blue Business Blog

Our Verdict

Choose a process that suits the size of your team and the way your business operates. Keep records consistent, review them regularly and give each person a clear responsibility. When evaluating a new tool, work through a realistic example from beginning to end. Use what you learn to decide whether the change will simplify your daily work.

Pros

Handles all of the basic payroll functions
Easy to Understand UI
Easily Integrates with other Square apps
Flat-rate pricing with no hidden fees
Automatically files federal, state, and local taxes
Supports both W-2 employees and 1099 contractors

Cons

No HR Suite
Four business day direct deposit policy

Products & Pricing

Square Payroll offers two straightforward pricing plans to fit different business needs.

Full-Service Payroll:
Start by listing the tools and user accounts you need today. Compare the regular subscription price with any introductory offer, then check the cost of additional services. A trial is useful for testing your daily workflow before choosing a plan.
Contractor-Only Payroll:
$6 per contractor per month, with no base fee. Ideal for businesses that only work with independent contractors. It includes automated 1099-NEC filings and direct deposit payments.

Start by listing the tools and user accounts you need today. Compare the regular subscription price with any introductory offer, then check the cost of additional services. A trial is useful for testing your daily workflow before choosing a plan. Review billing terms directly with the provider and allow room for your business to grow.

Full-Service Payroll

$35 /mo

+ $6/mo fee per person paid

Contractor-only payroll

$6 /mo per person paid

In-depth review

Features and Functionality

Automated Payroll, Tax Filings & Reporting

Timecards, Tips & Commissions

Unlimited Payroll Runs & Payment Options

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.

Add-ons and Integrations

Connected tools can reduce repeated work across your business. Before enabling a connection, review which records it shares, how often information updates and who can access it. Test the connection with a small set of sample records. Keep a clear process for checking changes and resolving any differences between your systems.

Ease of Use

Consider how your team will learn the software and get help when questions arise. Explore the help centre, check the support channels and look for examples relevant to your business. An effective onboarding process should make everyday tasks clear and give you a reliable way to solve problems as your needs change. Consider how your team will learn the software and get help when questions arise.

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.

Customer Service

Consider how your team will learn the software and get help when questions arise. Explore the help centre, check the support channels and look for examples relevant to your business.