Teamwork vs Square Payroll
A head-to-head comparison to help you pick the right tool
Last updated: April 30, 2026
Teamwork
Teamwork is a project management platform built specifically for client-facing teams and agencies. It includes built-in time tracking, invoicing, and client portals that make it ideal for professional services businesses managing multiple client projects simultaneously. Teamwork helps agencies deliver projects on time and on budget while keeping clients informed.
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
- ✓Built specifically for agencies and client-facing teams
- ✓Built-in time tracking and invoicing saves money on separate tools
- ✓Client portal keeps clients informed without giving full system access
- ✓Strong resource and budget management features
Cons
- ✗Less suitable for internal team project management
- ✗Interface feels less modern than competitors
- ✗Some key features only on higher paid tiers
- ✗Can be complex to set up for new users
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
Teamwork vs Square Payroll: Side by Side
| Factor | Teamwork | Square Payroll |
|---|---|---|
| User Rating | N/A | N/A |
| Category | Project Management | Payroll Software |
| Pricing Model | Freemium | Paid |
| Starting Price | Free | Contact for pricing |
| Best For | Agencies and professional services firms managing multiple client projects | Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution |
| Our Pick | — | — |
Teamwork Features
- ✓Project management
- ✓time tracking
- ✓invoicing
- ✓client portals
- ✓resource management
- ✓milestones
- ✓Gantt charts
- ✓budgets
- ✓collaboration tools
Square Payroll Features
- ✓Payroll processing
- ✓tax filing
- ✓benefits administration
- ✓direct deposit
- ✓employee self-service
- ✓reporting
Pricing Comparison
Our Take
Choose Teamwork if agencies and professional services firms managing multiple client projects. Choose Square Payroll if small businesses and restaurants already using square pos wanting a simple integrated payroll solution.
Best For
Agencies and professional services firms managing multiple client projects
Best For
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution
Also Consider
If neither Teamwork nor Square Payroll is the right fit, Wrike is worth evaluating.
Wrike
Marketing and creative teams needing enterprise project management with approvals and proofing
From Free
Frequently Asked Questions
What is the difference between Teamwork and Square Payroll?
Teamwork is best for agencies and professional services firms managing multiple client projects. Square Payroll is best for small businesses and restaurants already using square pos wanting a simple integrated payroll solution.
Which is better, Teamwork or Square Payroll?
Choose Teamwork if agencies and professional services firms managing multiple client projects. Choose Square Payroll if small businesses and restaurants already using square pos wanting a simple integrated payroll solution.
How much does Teamwork cost?
Teamwork starts at Free. Pricing model: Freemium.
How much does Square Payroll cost?
Visit Square Payroll website for current pricing.
Who should use Teamwork?
Agencies and professional services firms managing multiple client projects
Who should use Square Payroll?
Small businesses and restaurants already using Square POS wanting a simple integrated payroll solution