Square Payroll vs Insightly
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.
Insightly
Insightly is a CRM and project management platform designed for growing businesses. It uniquely combines sales pipeline management with post-sale project delivery so teams can manage the full customer lifecycle in one place. Insightly is popular with professional services firms and companies that need to track complex projects alongside their sales pipeline.
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
- ✓Unique combination of CRM and project management in one tool
- ✓Good free plan for up to 2 users
- ✓Strong workflow automation on paid plans
- ✓Good fit for professional services businesses
Cons
- ✗Interface feels dated compared to modern CRM tools
- ✗Customer support can be slow on lower tiers
- ✗Mobile app is less polished than competitors
Square Payroll vs Insightly: Side by Side
| Factor | Square Payroll | Insightly |
|---|---|---|
| User Rating | N/A | N/A |
| Category | Payroll Software | CRM Software |
| Pricing Model | Paid | Freemium |
| Starting Price | Contact for pricing | Free |
| Best For | Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution | Growing businesses that need CRM and project management in one platform |
| Our Pick | — | — |
Square Payroll Features
- ✓Payroll processing
- ✓tax filing
- ✓benefits administration
- ✓direct deposit
- ✓employee self-service
- ✓reporting
Insightly Features
- ✓Contact and lead management
- ✓pipeline management
- ✓project management
- ✓workflow automation
- ✓email marketing
- ✓reporting
- ✓integrations
Pricing Comparison
Our Take
Choose Square Payroll if small businesses and restaurants already using square pos wanting a simple integrated payroll solution. Choose Insightly if growing businesses that need crm and project management in one platform.
Best For
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution
Best For
Growing businesses that need CRM and project management in one platform
Also Consider
If neither Square Payroll nor Insightly 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 Insightly?
Square Payroll is best for small businesses and restaurants already using square pos wanting a simple integrated payroll solution. Insightly is best for growing businesses that need crm and project management in one platform.
Which is better, Square Payroll or Insightly?
Choose Square Payroll if small businesses and restaurants already using square pos wanting a simple integrated payroll solution. Choose Insightly if growing businesses that need crm and project management in one platform.
How much does Square Payroll cost?
Visit Square Payroll website for current pricing.
How much does Insightly cost?
Insightly starts at Free. Pricing model: Freemium.
Who should use Square Payroll?
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution
Who should use Insightly?
Growing businesses that need CRM and project management in one platform