POS Comparisons

Square vs Retail Pro: Which POS Is Better? (2025)

By Mauricio Nov 18, 2025 3 min read

When comparing Square vs Retail Pro, you’re looking at two distinct approaches to multi-industry point-of-sale technology. Square, rated 4.7/5, offers Small retail shops, food trucks, service businesses, and startups. Meanwhile, Retail Pro, rated 4.0/5, provides Multi-store specialty retailers. Let’s dive into the details to help you make an informed decision.

Quick Comparison: Square vs Retail Pro

FeatureSquareRetail Pro
CategoryMulti-IndustryRetail
Starting PriceFree (2.6% + 10¢ per transaction)Contact for pricing
Rating4.7/54.0/5
Target BusinessSmall BusinessMid-Market to Enterprise
Pricing ModelFreemiumQuote-based
Free TrialNoNo
Free VersionYesNo
Best ForSmall retail shops, food trucks, service businesses, and startupsMulti-store specialty retailers

Square Overview

Square is a comprehensive payment and point-of-sale platform that helps businesses of all sizes accept payments, manage inventory, and grow their business. Known for its iconic card reader and user-friendly interface.

Square is offered by Block, Inc. (formerly Square, Inc.) (founded 2009) based in San Francisco, CA. The system focuses on Retail, Restaurants, Services, Appointments.

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Key Features:

  • Free POS app
  • Inventory management
  • Employee management
  • Customer directory
  • Analytics dashboard
  • Online ordering

Retail Pro Overview

Retail Pro is an enterprise retail management software for specialty retailers. Offers POS, inventory management, and customer engagement tools for multi-store operations.

Retail Pro is offered by Retail Pro International (founded 1986) based in Folsom, CA. The system focuses on Specialty Retail, Apparel, Multi-store.

Key Features:

  • POS
  • Inventory Management
  • Multi-store
  • Customer Management
  • Reporting
  • E-commerce Integration

Feature Comparison

Square Features:

  • Free POS app
  • Inventory management
  • Employee management
  • Customer directory
  • Analytics dashboard

Retail Pro Features:

  • POS
  • Inventory Management
  • Multi-store
  • Customer Management
  • Reporting

When comparing features, Square stands out with No monthly fees, while Retail Pro differentiates itself with Enterprise retail focus. Your choice should depend on which features align better with your specific business requirements.

Pricing Comparison

Pricing AspectSquareRetail Pro
Starting PriceFree (2.6% + 10¢ per transaction)Contact for pricing
Pricing ModelFreemiumQuote-based
Price RangeBudgetPremium
Free TrialNot availableNot available
Free VersionYesNo

Square is more budget-friendly, making it a better choice for cost-conscious businesses. Consider the total cost of ownership including hardware, processing fees, and add-on modules when making your decision.

Pros and Cons

Square

Pros:

  • No monthly fees for basic plan
  • Easy setup and use
  • Excellent mobile app
  • Strong ecosystem of add-ons
  • Transparent pricing

Cons:

  • Transaction fees can add up
  • Limited customization
  • Account stability concerns for high-risk businesses

Retail Pro

Pros:

  • Enterprise scalability
  • Deep inventory features
  • Multi-store management
  • Customizable

Cons:

  • High cost
  • Complex implementation
  • Requires IT resources

Who Should Choose Square?

Square is ideal for Small retail shops, food trucks, service businesses, and startups. The system is particularly well-suited for Retail, Restaurants, Services, Appointments.

However, Square may not be the best fit for Large enterprises needing deep customization.

Who Should Choose Retail Pro?

Retail Pro is ideal for Multi-store specialty retailers. The system is particularly well-suited for Specialty Retail, Apparel, Multi-store.

However, Retail Pro may not be the best fit for Small single-location stores.

Our Recommendation

Both Square and Retail Pro are solid POS solutions, but they excel in different areas. Choose Square if you’re Small retail shops, food trucks, service businesses, and startups. Choose Retail Pro if you’re Multi-store specialty retailers. Square has a higher user rating (4.7 vs 4.0). Also, choose Square if you want to start with a free version. We recommend trying demos or free trials of both systems before making your final decision.