"Square is one of the biggest digital payment processors in the world today"
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  • Covers all payroll needs
  • Simple platform to use
  • Good integration with other Square apps
  • No site for HR ·
  • Direct deposit policy is four days
  • Some accounting apps don’t integrate
Company Background

Square is one of the biggest digital payment processors in the world today and it also has expanded into the payroll space. Its payroll system is completely cloud-based and is going to be a good fit for both small and medium-sized businesses. A range of bookkeeping functions can also be completed, while payroll can be managed automatically. This includes the filing of relevant taxes on time.


Plans & Pricing

There is a straightforward pricing system in place with the Square payroll offering. There are two different plans to choose from. The first of these is for both employees and contractors and it will cost $29 each month, as well as $5 per employee or contractor that gets paid in a given month.

The other plan will only be for 1099 contractors and it will cost just $5 each month and no monthly charge. This is a very good pricing plan and will be an ideal fit for a lot of smaller businesses. There is also a free trial period on offer, allowing you to explore these options without committing straight away.

Among the features that are offered as part of Square payroll included the filing of local, state, and federal taxes, as well as managing benefits, and full service for payroll needs. There is no annual contract that you need to commit to and there is even a feature for those hospitality companies that handle tips. This system sees the tracking and subsequent distribution of these tips.

Contractors only
up to 1,099 contractors
FREE Trial
Contractors & Employees
+ $5/mo/employee
FREE Trial
Features & Functionality
General Features

Automating key processes

One of the best features offered by Square’s payroll offering is the automatic calculating and filing of tax payments. This covers local, state, and federal taxes. You will also have your payroll processes automated in a similar fashion. This means that timesheets, salary info, overtime, etc. will be automatically taken into consideration.

There is the option for the payments to be sent via paper check or direct deposit. The administration of health and retirement benefits couldn’t be easier and there are now even capabilities to provide on-demand payment to workers.

Simply interface for workers

Contractors and employees can create their own accounts as part of Square payroll. This allows them to always be able to access their payroll info. This includes tax info, pay stubs, benefits, and so on. They can update different info, such as their tax withholdings and direct deposit accounts.

Management of benefits

Small businesses are able to choose and manage different types of benefits packages for their workers. This includes the likes of retirement benefits and health insurance. The employer is able to set the number of deductions for the paychecks to cover the various benefits for a given worker. Employees will use their personal payroll accounts to sign up for the benefits, meaning that there will be no paperwork on the business owner’s end.

Regular releases of new features

Square is known for being very innovative and it is regularly releasing new types of payroll features to make the user experience even better. Recent improvements include on-demand pay and instant payments. Over time, it is likely that more and more great features will be issued by Square.

  • 401(k) Tracking
  • Benefits Management
  • Check Printing
  • Direct Deposit
  • Multi-Country
  • Multi-State
  • Payroll Outsourcing
  • Payroll Reporting
  • Self Service Portal
  • Tax Compliance
  • Vacation/Leave Tracking
  • W-2/1099 Preparation
  • Wage Garnishment
Attendance Tracking
  • Calendar Management
  • Employee Scheduling
  • FMLA Tracking
  • Overtime Calculation
  • Reporting/Analytics
  • Self Service Portal
  • Time Tracking
Supported Devices
  • Windows
  • Android
  • iPhone/iPad
  • Mac
  • Web-based
Pricing Model
  • Monthly Payment
  • One-Time Payment
  • Annual Subscription
Ease of Use

It can take some time for you to get fully set up with Square, particularly if there is a lot of prior data that has to be entered into the system. In terms of the navigation system, it is pretty much straightforward. Once you get up and running, you will be able to manage all relevant processes from the same dashboard.

However, there is still some work to be done to make the overall payroll offering to be as user-friendly as many of Square’s competitors. In terms of employee accounts, this side of the platform has been well done. It is simple for workers to create an account and manage their various types of payments.

Customer Support

There is a good level of quality replies when you pose a question or query to the Square support team. You can choose between live chat, email, and phone support. Most of these options will only be available during normal working hours. You will also get access to a somewhat limited collection of FAQs.

Phone Support
Phone Support
Available on weekdays on a toll-free number from 9am to 9pm CT
Live Online Chat
Live Online Chat
Available with extended response times
Available- response within 24-48 hours
Limited range of FAQs available
Final Word

The Square payroll offering has a good range of features that covers all of the necessary functions that a small business needs to be taken care of. While it is still not the most user-friendly of platforms and it has a limited selection of integrations, these aspects are likely to improve over time. The pricing plans are very affordable and this is a no-brainer payroll solution if you already use other Square solutions.

Andrew O'Malley
Author: Andrew O'Malley
Andrew is a freelance writer who has been crafting valuable pieces of content relating to personal finance for more than five years. Previously, he studied Economics and Finance at university and he has professional qualifications relating to financial advice.