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Square Payroll vs CheckMark Payroll: Which Payroll Software Is Better?


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

Last Updated: April 25, 2025

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

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

 

Square Payroll vs CheckMark Payroll Reviews

Square PayrollCheckMark Payroll
Trustpilot Rating4.23.5
Number of Trustpilot Reviews40490
iPhone App Rating4.8not available
Number of iPhone App Reviews5not available
Android App Rating3.8not available
Number of Android App Reviews2660not available

Square Payroll vs CheckMark Payroll Pricing

Square PayrollCheckMark Payroll
Free Trialn/aYes
Free Trial Lengthn/a2 months
Cheapest Plan NamePay Contractors OnlyCheckMark Payroll Pro
Cheapest Plan Cost Per Month$n/a$n/a
Mid Priced Plan Namen/an/a
Mid Priced Plan Cost Per Month$n/a$n/a
Top Plan NamePay Employees & ContractorsCheckMark Payroll Pro+
Top Plan Cost Per Month$41$619

Square Payroll vs CheckMark Payroll Features

FeaturesSquare PayrollCheckMark Payroll
Target Business SizeSmall businessMid size 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✔✘

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

CheckMark Payroll CheckMark Payroll Pro Features

  • Self Service Payroll
  • Automatic Payroll Calculation
  • Unlimited Companies
  • Unlimited Salaried & Hourly Employees
  • Unlimited Payrolls (Regular, Bonus, Off-Cycle, etc.)
  • All Pay Frequencies
  • Multiple Pay Rates
  • MICR Encoded Check Printing
  • ACH Direct Deposit
  • Printing & E-Filing of Forms 941, 940, 944, 943, W-2, & W-3
  • Employer Payroll Tax Filings
  • Access to 40+ Types of Payroll Reports
  • Employee Benefits (Health, Retirement, Insurance, etc.)
  • Customized Vacation and Sick Leave Policies
  • Customized Deductions and Garnishments
  • Up to 90 mins within 12 months
  • Online access to program fixes

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

CheckMark Payroll CheckMark Payroll Pro+ Features

  • Self Service Payroll
  • Automatic Payroll Calculation
  • Unlimited Companies
  • Unlimited Salaried & Hourly Employees
  • Unlimited Payrolls (Regular, Bonus, Off-Cycle, etc.)
  • All Pay Frequencies
  • Multiple Pay Rates
  • MICR Encoded Check Printing
  • ACH Direct Deposit
  • Printing & E-Filing of Forms 941, 940, 944, 943, W-2, & W-3
  • Employer Payroll Tax Filings
  • Access to 40+ Types of Payroll Reports
  • Employee Benefits (Health, Retirement, Insurance, etc.)
  • Customized Vacation and Sick Leave Policies
  • Customized Deductions and Garnishments
  • Up to 300 mins of support within 12 months
  • Exclusive Pro+ toll-free phone number
  • Top-of-the-queue priority
  • Reduced data recovery rates
  • Online access to program fixes
  • Exclusive Pro+ Support Live Chat

Square Payroll vs CheckMark Payroll Pro & Cons

Square PayrollCheckMark Payroll
Pros
  • Mobile App
  • Self Service
  • User Friendly
  • Direct deposit option
  • Easy to use and interfaces with CheckMark’s Accounting program, MultiLedger
  • Automated reports
Cons
  • Not User Friendly
  • Room for Improvement
  • Slow
  • Technical support, glitches with Mac
  • High cost
  • More features like direct sms, email, other tax purpose forms

Other Payroll Software Comparisons

  • Patriot Software vs Ready Pay by HR3
  • Patriot Software vs Payfit
  • OnPay vs Heartland
  • Gloroots vs Dayforce
  • Gusto vs Fingercheck
  • Oytser HR vs PayCaptain
  • Sage vs Proliant
  • Paycom vs PDS Vista Payroll
  • PayCaptain vs TriNet
  • Aruti vs TriNet

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