Home>Running Payroll

Mailed Physical Checks with Square Payroll

Square Payroll partners with Checkeeper to provide Square Payroll subscribers with the option to pay your team with printed, physical checks mailed to your business overnight. Checks are mailed with your bank account information, business details, and shipped off via USPS or UPS next-day.

How it works

You’ll navigate to the Square Payroll sign up page with Checkeeper and select Create Account. You’ll input your personal information, banking information, and business location to set up the account. From there, you’ll link Square in the Add-Ons tab. Once you’ve set up your account with Checkeeper and linked it with Square Payroll in the Checkeeper portal, you’ll be able to upload Payroll CSV reports from Square Payroll directly into Checkeeper to obtain printed and mailed checks. You’ll be able to select specific team members that need mailed, physical checks while excluding any team members that utilize direct deposit or another payment method.

How to sign up with Checkeeper

1. Visit the Square Payroll sign up page with Checkeeper and select Create Account.
2. Enter your first and last name, email address, and create a password.
3. Enter your business details, business name, and business address.
4. Check your email for an activation link.

Pricing and billing

When you set up an account with Checkeeper, you will automatically receive a 14-day free trial. For a limited time, Checkeeper is offering your first payroll mailing free, up to 10 checks).

Checkeeper pricing is based on the number of checks being printed, batched, and mailed. You will purchase credits directly from Checkeeper in your account portal. Printed and mailed checks that are sent via first-class USPS are $1.25 per check. 

Credits Price
10 credits (10 checks) $12.50
20 credits (20 checks) $25.00
50 credits (50 checks) $62.50
100 credits (100 checks) $125.00
500 credits (500 checks) $625.00

Note: Paycheck stubs that are sent through Square Payroll should continue to be the primary source of truth for your team member's wage breakdowns, and can be accessed through your online Square dashboard or the Square Team app.

How to mail checks from Square Payroll with Checkeeper

1. Login to your Checkeeper account and navigate to the Add-ons tab from the sidebar menu.
2. Find the Square logo and click the blue Connect Square button. Note: You won’t actually login to your Square account at this point-- you’re just activating the Square add-on.
3. Download your payroll checks. To do this, open a new tab in your browser, and navigate to squareup.com. Click Log in and enter the email address and password for your Square account.
4. Navigate to your online Square Payroll dashboard. If you’ve already processed the payroll you wish to mail checks for, you’ll navigate to the History & Reports tab to select the payroll run.
5. If you haven’t processed the payroll run you wish to mail checks for, select Pay Employees. Once you’ve processed the payroll run, you’ll see the Actions dropdown menu on the Withdrawal Summary screen.
6. Download your payroll checks by clicking the Actions dropdown menu and selecting Export to CSV. Clicking Export to CSV will download a payroll summary CSV file, which you will upload to Checkeeper so you can get those checks printed and mailed out. Note: Make sure you submit your payroll run before the 4pm EST for same day mailing.
7. Go back to the Square Payroll tab in your Checkeeper account and click Browse, or simply drop your payroll CSV file right into the importer.
8. Confirm the number of payroll checks to import and give each one a quick review to make sure all of your check information has imported successfully. Note: The only address that’s pulled from Square Payroll is the business address so your checks won’t have a payee address on them. You can add each payee’s address to these checks if you wish, but it’s not necessary if you plan on bundling and overnighting your payroll in a single package, which is what we recommend.
9. You will now see all of your payroll checks waiting in your Checkeeper registry. To mail the checks, tick the box next to each check you want mailed and click Mail Checks.
10. If this is your first time mailing checks through Checkeeper, you’ll need to follow the fulfillment set up steps under the Check Mailing tab. Keep in mind, the account number, routing number, and signature you enter here are the ones that will be used to print your checks. This is also where you’ll purchase credits for check mailing.

The new Batch Mailing feature is specifically designed for payroll-- you can bundle all payroll checks together and overnight them all to the same location. Essentially, you’ll be able to run payroll and then have payroll checks mailed and delivered the very next day.

Note: Checks must be submitted for mailing before 4pm EST to qualify for same-day mailing.

You can read more in the Checkeeper Support Center.

Support with Checkeeper

We encourage customers to email support@checkeeper.com whenever assistance
is needed to facilitate a quick response. But if direct contact is needed we’re happy to provide those details.

One credit is equal to one check printed, placed in an envelope, and mailed via first-class USPS. Additional services do cost extra credits, however that rate can change to get you the best deal.


How long do checks take to be delivered?

Check orders received before 4pm EST will be mailed the same day they’re submitted, Monday through Friday. Typical USPS first class delivery times are between 1-4 business days.

Where are the checks mailed from?

Checkeeper has two mail centers. One located in South Carolina and the other in Wisconsin. To expedite the delivery time, your check orders are automatically routed to the closest mail center depending on the check’s mailing destination.

Why does Checkeeper need my account and routing information?

Checks are printed (in MICR) with your provided account and routing details because Checkeeper doesn’t handle funds in any way, we simply print your details on the check for you- it’s as if you were printing and mailing the check yourself.

Where are the checks mailed?

The only address that’s pulled from Square is the business address, so your checks won’t have your employee’s address on them. You can add each employee’s address to these checks if you wish, but it’s not necessary if you plan on bundling and overnighting your payroll in a single package, which is what we recommend.