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Heartland vs Square Payroll: Which Payroll Software Is Better?


Disclosure: We may earn commissions if you shop through the links below.

Last Updated: May 22, 2025

Both Heartland and Square Payroll are leading payroll software solutions, but which one is better for you and your business?

Below we compare Heartland and Square Payroll across nearly 50 different data points to help you make find the right one.

 

Heartland vs Square Payroll Reviews

HeartlandSquare Payroll
Trustpilot Rating04.2
Number of Trustpilot Reviews04049
iPhone App Rating2.34.8
Number of iPhone App Reviews1535
Android App Rating3.63.8
Number of Android App Reviews3312660

Heartland vs Square Payroll Pricing

HeartlandSquare Payroll
Free Trialn/an/a
Free Trial Lengthn/an/a
Cheapest Plan NameEssentialsPay Contractors Only
Cheapest Plan Cost Per Month$By request$n/a
Mid Priced Plan NameAdvancedn/a
Mid Priced Plan Cost Per Month$By request$n/a
Top Plan NameCompletePay Employees & Contractors
Top Plan Cost Per Month$By request$41

Heartland vs Square Payroll Features

FeaturesHeartlandSquare Payroll
Target Business SizeEnterpriseSmall business
Unlimited Payrolls✘✔
Automated Tax Filing & Payments✔✔
E-sign I-9 & W-4✘✘
Live Customer Support✔✔
Third-Party Integrations✘✔
Ability To Manage Employee Benefits✘✔
Employee Access To Platform✔✔
Direct Deposit✔✔
Expense Reimbursement✘✘
Time Off Accrual✔✔
Pre-Tax Deductions✔✔
Wage Garnishment✔✔
Background Checks✔✘
Check Printing✔✔
Check Delivery✔✔
API✘✔

Heartland Essentials Features

  • Payroll Processing
  • Tax Filing – Federal, State, Local
  • Tax Payments – Federal, State, Local
  • Payment Options – Check, Direct Deposit, Pay Card
  • New Hire Reporting
  • Child Support Reporting
  • Garnishment Support
  • Payroll Reporting – Standard, Exports, Custom
  • Employee Mobile Access
  • Live, Dedicated Support
  • Onboarding for New Hires, Integrated with Payroll
  • Employment Verification
  • Electronic Submission of New Hire Documentation
  • Work Opportunity Tax Credit (WOTC) Screening

Square Payroll Pay Contractors Only Features

  • We mail all 1099-NEC forms
  • M–F 6 a.m. to 6 p.m. PT support
  • Pay by check, direct deposit, or Cash App
  • Free seasonal inactivity
  • All features included, with no hidden fees
  • No commitment, cancel anytime

Heartland Complete Features

  • Payroll Processing
  • Tax Filing – Federal, State, Local
  • Tax Payments – Federal, State, Local
  • Payment Options – Check, Direct Deposit, Pay Card
  • New Hire Reporting
  • Child Support Reporting
  • Garnishment Support
  • Payroll Reporting – Standard, Exports, Custom
  • Employee Mobile Access
  • Live, Dedicated Support
  • Onboarding for New Hires, Integrated with Payroll
  • Employment Verification
  • Electronic Submission of New Hire Documentation
  • Work Opportunity Tax Credit (WOTC) Screening
  • Job Postings to Top Job Boards*
  • Text to Apply
  • Candidate Screenings*
  • Applicant Tracking
  • HR Library
  • HR Tracking – Training, Certifications, IDs, etc.
  • Employee Handbook Builder
  • Job Descriptions
  • Labor Law Posters
  • Live HR Support

Square Payroll Pay Employees & Contractors Features

  • No additional fees
  • Full-service payroll
  • Payroll for employees and contractors
  • Automatic payroll tax calculations
  • All tax filings and payments
  • Multistate payroll
  • Live support for account setup
  • Timecards and employee app
  • Track and import tips and commissions
  • We mail W-2s and 1099-NEC forms
  • Pay by check, direct deposit, or Cash App
  • M–F 6 a.m. to 6 p.m. PT support
  • No commitment, cancel anytime
  • Unlimited pay runs per month
  • Free seasonal inactivity

Heartland vs Square Payroll Pro & Cons

HeartlandSquare Payroll
Pros
  • Highly Responsive Account Representative
  • Extremely Easy to Use Online System
  • Convenient Onboarding Process with Heartland Hire
  • Mobile App
  • Self Service
  • User Friendly
Cons
  • Missing Email Reminders
  • Lack of Local Support
  • Inconvenient Payroll Repeating Process
  • Not User Friendly
  • Room for Improvement
  • Slow

Other Payroll Software Comparisons

  • PrimePay vs Darwinbox
  • Fingercheck vs Trolley
  • ADP vs Workday
  • Trolley vs HRONE
  • Workday vs TriNet
  • ADP vs Gloroots
  • Heartland vs TriNet
  • greytHR vs Inova Payroll
  • SurePayroll vs Justworks
  • Zenefits vs Wagepoint

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