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June 6, 2024
XX min read

Charlie vs Square Payroll


When it comes to HRIS tools, choosing the right one can significantly impact your business's efficiency and employee satisfaction. Charlie and Square Payroll are two popular options in this space, each offering distinctive features tailored to streamline HR processes.

Charlie is a cloud-based HR software that makes all HR processes easy. With Charlie, you can onboard new hires, store company documents, book and manage time off, run productive reviews, and get professional HR advice. It’s an easy, holistic system for managing your People needs.

Square Payroll, on the other hand, is an online payroll service trusted by small businesses. It simplifies payroll management with features like automatic tax filings, employee self-service, and seamless integration with Square's point-of-sale system.

In this comparison, we'll dive deep into the features, pros, cons, similarities, differences, and ideal use cases of both tools to help you determine which one aligns best with your HR needs.

Charlie Overview

Charlie is designed to be a comprehensive HR platform that handles a wide range of HR-related tasks, simplifying the management of people within your organization.

Key Features

  • Onboarding New Hires: Streamline the onboarding process with customizable checklists and automated workflows.
  • Document Storage: Securely store and manage all company documents in one place.
  • Time Off Management: Easily book, approve, and track employee holidays and other leave types.
  • Performance Reviews: Conduct meaningful reviews with customizable templates and 360-degree feedback mechanisms.
  • HR Advice: Access to professional HR guidance to handle complex employee issues.
  • Employee Database: Maintain an up-to-date record of all employee information and track key metrics.
  • Task Management: Create and assign tasks to ensure important HR activities are completed on time.

Square Payroll Overview

Square Payroll is crafted to cater specifically to the payroll needs of small businesses, ensuring compliance and accuracy with minimal effort.

Key Features

  • Automated Tax Filings: Automatically calculates and files federal, state, and local taxes.
  • Employee Self-Service: Employees can manage their own information, including direct deposit options, via a secure portal.
  • Time Tracking Integration: Seamlessly integrates with Square's point-of-sale system for accurate time tracking.
  • Direct Deposits: Easy setup for timely direct deposits to employee bank accounts.
  • Benefits Management: Manage healthcare, retirement, and other employee benefits within the platform.
  • Compliance Management: Ensures payroll compliance with federal and state regulations.
  • Custom Payroll Reports: Generate detailed reports to gain insights into payroll expenses and trends.


  • Cloud-Based: Both Charlie and Square Payroll are cloud-based solutions, ensuring easy access and updates from anywhere.
  • Employee Self-Service: Both platforms offer self-service portals where employees can manage their own information, reducing administrative burdens.
  • Compliance Support: Both tools provide features that aid in compliance with employment laws and regulations.
  • Integration Capabilities: Each tool can integrate with other software systems, although they focus on different areas (HR management vs. payroll).


  • Primary Focus: Charlie focuses on a broad spectrum of HR functions, including onboarding, performance reviews, and HR advice. Square Payroll, meanwhile, zeroes in on payroll management and related tasks.
  • Feature Set: Charlie includes features for document storage, task management, and comprehensive employee records. Square Payroll specializes in automated tax filings, direct deposits, and time tracking integration.
  • Target Audience: Charlie is designed for businesses seeking an all-in-one HR solution, while Square Payroll is aimed at small businesses needing efficient payroll processing, particularly those already using Square's point-of-sale system.
  • Pricing Structure: The pricing models may differ, with Charlie potentially offering tiered pricing based on the range of HR functionalities, and Square Payroll possibly following a per-employee pricing model.

Pros and Cons



  • Comprehensive HR functionalities in one platform.
  • Customizable onboarding and performance review processes.
  • Professional HR advice.
  • Easy management of time off and employee records.


  • Might be overwhelming for businesses only needing basic HR functions.
  • Potentially higher cost given the broad feature set.
  • May require time to fully leverage all features effectively.

Square Payroll


  • Simplifies payroll processing with automated tax filings and compliance.
  • Seamless integration with Square point-of-sale.
  • Employee self-service for payroll management.
  • Cost-effective for small businesses.


  • Limited to payroll-related functions without broader HR capabilities.
  • May not be suitable for larger organizations with more complex HR needs.
  • Dependent on Square ecosystem for optimal use cases.

Use Cases


  • Growing Companies: Ideal for businesses experiencing growth and needing to streamline their HR processes, from hiring to performance management.
  • Startups: Perfect for startups that require professional HR guidance and a holistic system for managing people operations.
  • Companies with diverse HR needs: Suits businesses that need a wide range of HR functions, including document storage and task management.

Square Payroll

  • Small Businesses: Best for small businesses seeking a straightforward payroll processing tool, particularly those utilizing Square's point-of-sale.
  • Retail and Hospitality: Excellent for businesses in retail and hospitality that need seamless integration of payroll with time tracking and point-of-sale systems.
  • Employers with simple HR requirements: Suitable for companies with a primary focus on payroll and basic employee management.


Comparing Charlie and Square Payroll reveals that each tool excels in its own domain, catering to distinct business needs. Charlie offers a comprehensive HR management solution with a multitude of features to streamline various people processes. It is ideal for businesses looking for a holistic approach to HR, encompassing everything from onboarding to professional HR advice.

Square Payroll, in contrast, focuses on the payroll aspect, providing a robust and straightforward solution for small businesses. Its automated tax filings, seamless time tracking integration, and employee self-service features make it a reliable choice for small businesses, particularly those already using Square's point-of-sale system.

In summary, if your business requires a full-fledged HR solution with advanced features and professional guidance, Charlie is likely the better choice. However, if your primary need is efficient payroll processing with solid integration capabilities, Square Payroll should be your tool of choice. Evaluate your specific needs, consider the pros and cons discussed, and choose the tool that aligns best with your company's HR requirements.

Key takeaways 🔑🥡🍕

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