Square Payroll vs Workday Comparison: Reviews, Features, Pricing & Alternatives in 2026

Detailed side-by-side comparison to help you choose the right solution for your team

Updated Apr 2026 8 min read

Square Payroll

0.0 (0 reviews)

Square Payroll is a full-service payroll software that automates tax filings, employee payments, and benefits management for small businesses using integrated time tracking and point-of-sale data.

Starting at Free
Free Trial NO FREE TRIAL
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Workday

0.0 (0 reviews)

Workday is a unified cloud platform that manages your global workforce, financial operations, and planning processes through a single AI-driven system to streamline enterprise resource management and organizational growth.

Starting at --
Free Trial NO FREE TRIAL

Quick Comparison

Feature Square Payroll Workday
Website squareup.com workday.com
Pricing Model Subscription Custom
Starting Price Free Custom Pricing
FREE Trial ✘ No free trial ✘ No free trial
Free Plan ✘ No free plan ✘ No free plan
Product Demo ✓ Request demo here ✓ Request demo here
Deployment saas mobile cloud mobile
Integrations Square POS QuickBooks Online Xero Homebase Deputy TSheets 7shifts Guideline SimplyInsured AP Intego Salesforce Slack Microsoft Teams Adobe Sign DocuSign ServiceNow Kronos ADP Microsoft 365 Google Workspace
Target Users solopreneur small-business mid-market enterprise
Target Industries retail restaurant professional-services
Customer Count 0 0
Founded Year 2009 2005
Headquarters San Francisco, USA Pleasanton, USA

Overview

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Square Payroll

Square Payroll simplifies how you pay your team by automating the most complex parts of business ownership. You can pay employees and contractors in just a few clicks, whether they are hourly or salaried. The platform automatically calculates, files, and pays your federal and state payroll taxes, ensuring you stay compliant without manual paperwork. Because it integrates directly with Square POS, your team's hours sync automatically, eliminating the need for manual data entry or messy spreadsheets.

You can manage everything from a single dashboard, including workers' compensation, health insurance, and 401(k) plans. The system supports flexible payment options like Instant Payments, allowing you to send funds to employees the same day they work. Whether you are running a single coffee shop or managing multiple retail locations, you get a straightforward tool that handles the back-office heavy lifting so you can focus on growing your business.

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Workday

Workday provides a unified cloud environment where you can manage your people, finances, and operational data in one place. Instead of toggling between disconnected systems, you get a single source of truth for everything from payroll and benefits to procurement and financial reporting. You can automate manual accounting tasks, track employee performance, and manage global compliance requirements through an intuitive interface designed for modern teams.

The platform is built specifically for mid-market and enterprise organizations that need to scale complex operations. You can use its built-in AI to surface talent insights, predict financial trends, and simplify repetitive administrative workflows. Because it operates on a single version of software, you always have access to the latest features and security updates without the headache of manual upgrades.

Overview

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Square Payroll Features

  • Automated Tax Filings Let the software calculate, file, and pay your state and federal payroll taxes automatically to ensure total compliance.
  • Time Card Sync Import employee hours directly from Square POS or the Team App to eliminate manual data entry errors.
  • Instant Payments Access your funds immediately and pay your team the same day they work using your Square Balance.
  • Benefits Integration Offer and manage health insurance, 401(k) plans, and workers' comp directly through your payroll dashboard.
  • Contractor Payments Pay your independent contractors via direct deposit and let the system generate and file 1099-NEC forms.
  • Employee Mobile App Give your team a dedicated app to track their hours, view pay stubs, and manage their tax forms.
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Workday Features

  • Human Capital Management. Manage the entire employee lifecycle from recruitment to retirement while tracking skills, performance, and global compensation in one place.
  • Financial Management. Streamline your core accounting processes, manage global spend, and gain real-time visibility into your financial health with automated reporting.
  • Adaptive Planning. Create flexible budgets and forecasts using real-time data so you can pivot your business strategy quickly when market conditions change.
  • Payroll and Cloud Connect. Process payroll accurately across multiple countries and integrate with external providers while maintaining a single record for every employee.
  • Talent Optimization. Identify skill gaps within your team and use AI-driven recommendations to match employees with new internal opportunities and growth paths.
  • Spend Management. Control your organization's indirect spend and streamline procurement workflows with automated invoice processing and strategic sourcing tools.

Pricing Comparison

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Square Payroll Pricing

Contractors Only
$0
  • $5 per person paid monthly
  • No monthly base fee
  • Direct deposit included
  • 1099-NEC generation and filing
  • Self-service contractor account
W

Workday Pricing

Pros & Cons

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Square Payroll

Pros

  • Seamless integration with Square Point of Sale
  • Automatic tax filing saves hours of manual work
  • Simple and transparent per-employee pricing model
  • Easy setup process for new business owners

Cons

  • Customer support can be difficult to reach
  • Limited advanced HR features for large corporations
  • Account freezes can occasionally delay payroll processing
A

Workday

Pros

  • Unified data source eliminates the need for multiple third-party integrations
  • Highly customizable reporting allows you to drill down into specific metrics
  • Regular automated updates ensure you always use the most current version
  • Excellent mobile app provides full functionality for managers on the go

Cons

  • Significant time investment required for initial implementation and setup
  • Steep learning curve for administrators managing complex backend configurations
  • Search functionality can be difficult to navigate for casual users
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