When I Work vs Square Payroll
A head-to-head comparison to help you pick the right tool
Last updated: April 30, 2026
When I Work
When I Work is an employee scheduling and time tracking platform designed for hourly and shift-based teams. It makes it easy for managers to build schedules, communicate with staff, and track attendance. When I Work is one of the most affordable scheduling tools on the market.
Square Payroll
Square Payroll is a simple and affordable payroll solution built for small businesses, especially those already using Square for payments. It handles full-service payroll, tax filings, and tip management automatically.
Pros
- ✓Very affordable pricing starting at just a few dollars per user
- ✓Easy-to-use scheduling with drag-and-drop interface
- ✓Good team messaging and shift swap tools
- ✓Simple time clock with GPS tracking
Cons
- ✗Limited features beyond scheduling and time tracking
- ✗No payroll processing or full HR suite
- ✗Reporting is basic compared to more comprehensive workforce tools
Pros
- ✓Very easy to use
- ✓Affordable flat pricing
- ✓Seamless Square POS integration
- ✓Handles tips and hourly workers well
- ✓Full-service tax filing included
Cons
- ✗Limited features for complex payroll needs
- ✗Not suited for larger businesses
- ✗HR features are basic
- ✗Best value only for Square ecosystem users
When I Work vs Square Payroll: Side by Side
| Factor | When I Work | Square Payroll |
|---|---|---|
| User Rating | N/A | N/A |
| Category | HR Software | Payroll Software |
| Pricing Model | Paid | Paid |
| Starting Price | $2.50/user/mo | Contact for pricing |
| Best For | Small businesses with hourly or shift-based workers | Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution |
| Our Pick | — | — |
When I Work Features
- ✓Shift scheduling
- ✓time clock
- ✓team messaging
- ✓attendance tracking
- ✓payroll export
Square Payroll Features
- ✓Payroll processing
- ✓tax filing
- ✓benefits administration
- ✓direct deposit
- ✓employee self-service
- ✓reporting
Pricing Comparison
Our Take
Choose When I Work if small businesses with hourly or shift-based workers. Choose Square Payroll if small businesses and restaurants already using square pos wanting a simple integrated payroll solution.
Best For
Small businesses with hourly or shift-based workers
Best For
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution
Also Consider
If neither When I Work nor Square Payroll is the right fit, Justworks is worth evaluating.
Justworks
Small businesses wanting Fortune 500 benefits
From $59/employee/mo
Frequently Asked Questions
What is the difference between When I Work and Square Payroll?
When I Work is best for small businesses with hourly or shift-based workers. Square Payroll is best for small businesses and restaurants already using square pos wanting a simple integrated payroll solution.
Which is better, When I Work or Square Payroll?
Choose When I Work if small businesses with hourly or shift-based workers. Choose Square Payroll if small businesses and restaurants already using square pos wanting a simple integrated payroll solution.
How much does When I Work cost?
When I Work starts at $2.50/user/mo. Pricing model: Paid.
How much does Square Payroll cost?
Visit Square Payroll website for current pricing.
Who should use When I Work?
Small businesses with hourly or shift-based workers
Who should use Square Payroll?
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution