Square Payroll vs Pilot
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.
Pilot
Pilot is a managed accounting service that combines software with a dedicated team of bookkeepers to handle your books each month. Built for startups and small businesses that want accounting done for them.
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
- ✓Fully managed bookkeeping service
- ✓Dedicated finance experts included
- ✓Built specifically for startups
- ✓Integrates with common startup tools
- ✓Good for venture-backed companies
Cons
- ✗More expensive than DIY software
- ✗Less control over day-to-day bookkeeping
- ✗Not suited for businesses wanting to manage their own books
- ✗US-focused
Square Payroll vs Pilot: Side by Side
| Factor | Square Payroll | Pilot |
|---|---|---|
| User Rating | N/A | N/A |
| Category | Payroll Software | Accounting Software |
| Pricing Model | Paid | Paid |
| Starting Price | Contact for pricing | Contact for pricing |
| Best For | Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution | Startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than DIY software |
| Our Pick | — | — |
Square Payroll Features
- ✓Payroll processing
- ✓tax filing
- ✓benefits administration
- ✓direct deposit
- ✓employee self-service
- ✓reporting
Pilot Features
- ✓Bookkeeping
- ✓tax preparation
- ✓financial reporting
- ✓dedicated bookkeeper
- ✓cash flow management
- ✓integrations
Pricing Comparison
Our Take
Choose Square Payroll if small businesses and restaurants already using square pos wanting a simple integrated payroll solution. Choose Pilot if startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than diy software.
Best For
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution
Best For
Startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than DIY software
Also Consider
If neither Square Payroll nor Pilot 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 Pilot?
Square Payroll is best for small businesses and restaurants already using square pos wanting a simple integrated payroll solution. Pilot is best for startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than diy software.
Which is better, Square Payroll or Pilot?
Choose Square Payroll if small businesses and restaurants already using square pos wanting a simple integrated payroll solution. Choose Pilot if startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than diy software.
How much does Square Payroll cost?
Visit Square Payroll website for current pricing.
How much does Pilot cost?
Visit Pilot website for current pricing.
Who should use Square Payroll?
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution
Who should use Pilot?
Startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than DIY software