Insightly vs Square Payroll
A head-to-head comparison to help you pick the right tool
Last updated: April 30, 2026
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.
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
- ✓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
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
Insightly vs Square Payroll: Side by Side
| Factor | Insightly | Square Payroll |
|---|---|---|
| User Rating | N/A | N/A |
| Category | CRM Software | Payroll Software |
| Pricing Model | Freemium | Paid |
| Starting Price | Free | Contact for pricing |
| Best For | Growing businesses that need CRM and project management in one platform | Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution |
| Our Pick | — | — |
Insightly Features
- ✓Contact and lead management
- ✓pipeline management
- ✓project management
- ✓workflow automation
- ✓email marketing
- ✓reporting
- ✓integrations
Square Payroll Features
- ✓Payroll processing
- ✓tax filing
- ✓benefits administration
- ✓direct deposit
- ✓employee self-service
- ✓reporting
Pricing Comparison
Our Take
Choose Insightly if growing businesses that need crm and project management in one platform. Choose Square Payroll if 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
Best For
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution
Also Consider
If neither Insightly nor Square Payroll is the right fit, Monday.com CRM is worth evaluating.
Monday.com CRM
Teams that want CRM and project management combined in one visual platform
From $12/user/mo
Frequently Asked Questions
What is the difference between Insightly and Square Payroll?
Insightly is best for growing businesses that need crm and project management in one platform. Square Payroll is best for small businesses and restaurants already using square pos wanting a simple integrated payroll solution.
Which is better, Insightly or Square Payroll?
Choose Insightly if growing businesses that need crm and project management in one platform. Choose Square Payroll if small businesses and restaurants already using square pos wanting a simple integrated payroll solution.
How much does Insightly cost?
Insightly starts at Free. Pricing model: Freemium.
How much does Square Payroll cost?
Visit Square Payroll website for current pricing.
Who should use Insightly?
Growing businesses that need CRM and project management in one platform
Who should use Square Payroll?
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution