Getting Started with Square

Tyler Atkinson
Aug 27, 2021

Hey there, and welcome to Checkeeper! We are joining forces Square and, as you can imagine, we’re pretty stoked about it. This here is your ultimate guide to getting started with Square and making the most of all the features this 🌶spicy🌶 new add-on has to offer.

Connecting Your Square Account

Start by navigating to app.checkeeper.com. Log in to your Checkeeper account if you have one, and if you don’t, well... my condolences; we’ll wait while you create one.


… :)


Alright, after logging in to your Checkeeper account, navigate to the Add-ons tab in the left sidebar menu.

Find Square, and click the blue “Connect Square” button. Now go ahead and get excited. 🕺 ‘Cause your life is about to change. (You won’t actually have to log in to your Square account at this point-- you’re just activating the Square add-on for now.)

Check it out! You should now have a fancy new tab in your left sidebar menu, dedicated specifically to managing your Square payroll.

Download Payroll Checks from Square

After you link your Square and Checkeeper accounts, it’s time to import 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.

Click “Sign In,” and then select a business or service to manage.

Once you’re in the dashboard, you’ll find the payroll icon at the top left. Click that! It’ll take you to your Square payroll dashboard. The payroll dashboard is where you can run payroll, manage your employees, view payroll history, pull reports, and complete a whole bunch of other super-awesome
payroll-related tasks.


For now, let’s explore how to actually get those payroll checks downloaded from Square and uploaded into your Checkeeper registry. If you’ve run payroll pretty recently and you’re ready to mail those checks, navigate to the History & Reports tab. Otherwise, click the blue “Pay Employees” button to run payroll now!

Once you’ve followed the steps in Square and completed payroll, 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 today! (Just make sure you submit them before the 4pm EST daily cutoff time.)

Mail Payroll Checks with Checkeeper

So you’ve run your payroll. You’ve downloaded those bois into a tidy little CSV file. Now, it’s time to mail those checks! 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.

Now this is exciting…

Confirm the number of payroll checks to import, and give each one a quick scan to make sure all your check information imported successfully.

Heads up, the only address that’s pulled from Square 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.

You will now see all your payroll checks waiting in your Checkeeper registry, just beggin’ to be mailed. To do this, tick the box next to each check you want mailed, and click the blue “Mail Checks” button to the right.
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 we’ll use to print your checks! This is also where you’ll purchase credits for check mailing.

Every time you mail checks, you’ll have a few different options for how exactly you want them mailed. Our new Batch Mailing feature is specifically designed for payroll-- bundle all payroll checks together, and overnight them to all to the same location. Essentially, it allows you to run payroll and then have those payroll checks mailed and then delivered the very next day*. Pretty darn cool, if we may say so ourselves.


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


Still Have Questions?