Square Payroll vs When I Work
A head-to-head comparison to help you pick the right tool
Last updated: April 30, 2026
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.
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.
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
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
Square Payroll vs When I Work: Side by Side
| Factor | Square Payroll | When I Work |
|---|---|---|
| User Rating | N/A | N/A |
| Category | Payroll Software | HR Software |
| Pricing Model | Paid | Paid |
| Starting Price | Contact for pricing | $2.50/user/mo |
| Best For | Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution | Small businesses with hourly or shift-based workers |
| Our Pick | — | — |
Square Payroll Features
- ✓Payroll processing
- ✓tax filing
- ✓benefits administration
- ✓direct deposit
- ✓employee self-service
- ✓reporting
When I Work Features
- ✓Shift scheduling
- ✓time clock
- ✓team messaging
- ✓attendance tracking
- ✓payroll export
Pricing Comparison
Which Should You Choose?
Choose Square Payroll if...
- →Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution
Our Take
Choose Square Payroll if small businesses and restaurants already using square pos wanting a simple integrated payroll solution. Choose When I Work if small businesses with hourly or shift-based workers.
Best For
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution
Best For
Small businesses with hourly or shift-based workers
Also Consider
If neither Square Payroll nor When I Work is the right fit, Multiplier is worth evaluating.
Multiplier
Startups and SMBs hiring internationally on a budget
From $40/contractor/mo
Frequently Asked Questions
What is the difference between Square Payroll and When I Work?
Square Payroll is best for small businesses and restaurants already using square pos wanting a simple integrated payroll solution. When I Work is best for small businesses with hourly or shift-based workers.
Which is better, Square Payroll or When I Work?
Choose Square Payroll if small businesses and restaurants already using square pos wanting a simple integrated payroll solution. Choose When I Work if small businesses with hourly or shift-based workers.
How much does Square Payroll cost?
Visit Square Payroll website for current pricing.
How much does When I Work cost?
When I Work starts at $2.50/user/mo. Pricing model: Paid.
Who should use Square Payroll?
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution
Who should use When I Work?
Small businesses with hourly or shift-based workers