15Five vs Square Payroll
A head-to-head comparison to help you pick the right tool
Last updated: April 30, 2026
15Five
15Five is a continuous performance management platform focused on weekly check-ins, OKRs, and employee engagement. It helps managers stay connected with their teams through structured feedback and recognition tools. 15Five is popular with remote and distributed teams that need async communication tools.
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
- ✓Simple and intuitive weekly check-in format that drives adoption
- ✓Strong OKR and goal-setting tools
- ✓Excellent manager training and coaching resources
- ✓Good engagement survey tools with benchmarking
Cons
- ✗Limited HR functionality beyond performance and engagement
- ✗No payroll or benefits administration
- ✗Reporting could be more advanced for data-driven HR teams
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
15Five vs Square Payroll: Side by Side
| Factor | 15Five | Square Payroll |
|---|---|---|
| User Rating | N/A | N/A |
| Category | HR Software | Payroll Software |
| Pricing Model | Paid | Paid |
| Starting Price | $4/user/mo | Contact for pricing |
| Best For | Companies focused on employee engagement and performance | Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution |
| Our Pick | — | — |
15Five Features
- ✓Weekly check-ins
- ✓OKRs
- ✓performance reviews
- ✓engagement surveys
- ✓manager training
Square Payroll Features
- ✓Payroll processing
- ✓tax filing
- ✓benefits administration
- ✓direct deposit
- ✓employee self-service
- ✓reporting
Pricing Comparison
Our Take
Choose 15Five if companies focused on employee engagement and performance. Choose Square Payroll if small businesses and restaurants already using square pos wanting a simple integrated payroll solution.
Best For
Companies focused on employee engagement and performance
Best For
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution
Also Consider
If neither 15Five 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 15Five and Square Payroll?
15Five is best for companies focused on employee engagement and performance. Square Payroll is best for small businesses and restaurants already using square pos wanting a simple integrated payroll solution.
Which is better, 15Five or Square Payroll?
Choose 15Five if companies focused on employee engagement and performance. Choose Square Payroll if small businesses and restaurants already using square pos wanting a simple integrated payroll solution.
How much does 15Five cost?
15Five starts at $4/user/mo. Pricing model: Paid.
How much does Square Payroll cost?
Visit Square Payroll website for current pricing.
Who should use 15Five?
Companies focused on employee engagement and performance
Who should use Square Payroll?
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution