Pilot vs Square Payroll
A head-to-head comparison to help you pick the right tool
Last updated: April 30, 2026
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.
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
- ✓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
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
Pilot vs Square Payroll: Side by Side
| Factor | Pilot | Square Payroll |
|---|---|---|
| User Rating | N/A | N/A |
| Category | Accounting Software | Payroll Software |
| Pricing Model | Paid | Paid |
| Starting Price | Contact for pricing | Contact for pricing |
| Best For | Startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than DIY software | Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution |
| Our Pick | — | — |
Pilot Features
- ✓Bookkeeping
- ✓tax preparation
- ✓financial reporting
- ✓dedicated bookkeeper
- ✓cash flow management
- ✓integrations
Square Payroll Features
- ✓Payroll processing
- ✓tax filing
- ✓benefits administration
- ✓direct deposit
- ✓employee self-service
- ✓reporting
Pricing Comparison
Our Take
Choose Pilot if startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than diy software. Choose Square Payroll if 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
Best For
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution
Also Consider
If neither Pilot nor Square Payroll is the right fit, Dext is worth evaluating.
Dext
Bookkeepers, accountants, and businesses with high receipt volumes wanting to eliminate manual data entry
From $15/mo
Frequently Asked Questions
What is the difference between Pilot and Square Payroll?
Pilot is best for startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than diy software. Square Payroll is best for small businesses and restaurants already using square pos wanting a simple integrated payroll solution.
Which is better, Pilot or Square Payroll?
Choose Pilot if startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than diy software. Choose Square Payroll if small businesses and restaurants already using square pos wanting a simple integrated payroll solution.
How much does Pilot cost?
Visit Pilot website for current pricing.
How much does Square Payroll cost?
Visit Square Payroll website for current pricing.
Who should use Pilot?
Startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than DIY software
Who should use Square Payroll?
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution