The Top 3 Invoicing, Billing, and Point of Sale Systems for Small Businesses in 2020

Updated: Jul 25, 2020

series map

>>> One: Accounting / Bookkeeping

>>> Two: Invoicing / Billing / Point of Sale

>>> Guide: The Invoicing / Billing / POS Software You Need

>>> Deep Dive: The Top 3 Invoicing / Billing / POS Systems [YOU ARE HERE]

>>> How-To: Setup Your Invoicing / Billing / POS Software [coming soon]

>>> Three: Workload Management

>>> Four: Customer Management [coming soon]

>>> Five: Domain Name / Website / Social Media [coming soon]


Square launched their first product in 2010, and fundamentally changed the possibilities for how small businesses processed payments.

Before Square, processing credit cards meant dealing with a merchant services dealer and bulky card-reader hardware. Then Square released the first mobile credit card reader - a simple little square dongle that plugged into the headphone jack on any smartphone. With that single device, anyone could start swiping credit cards and accepting payments on their phone.

Gone are the days of the headphone jack being standard on smartphones, but Square has continued to grow and expand as technology changes - now offering Bluetooth card readers to allow business owners to process credit cards using current smartphones.

Square's full list of functionality is quite lengthy - now including just about everything a small business owner might need to manage the movement of the money in their company. Square produces a variety of point of sale hardware options, both fixed-station and mobile. Square can also process and send invoices via email (for a more services-oriented business). Moreover, Square includes eCommerce tools to help process payments on your website, as well as tools to manage payroll, loyalty programs, digital gift cards, and built-in reporting for added visibility into your business. You can even get debit cards and business loans through Square.

And Square is easy to set up, and you can even test many of their features online without creating an account (for example, you can send a test invoice to yourself to see what your customers would experience).

Square makes it simple and straightforward for your customers to pay you - and includes customizable colors and logos to personalize for your business.

Overall, Square offers the best of both worlds between in-person and online payments.

Square - for every transaction processed in-person through Square, you pay a $0.10 flat fee + 2.6% of the transaction; for every transaction processed online through Square, you pay a $0.30 flat fee + 2.9% of the transaction; point of sale hardware costs from $50 to $800 depending on device(s), payment plans offered

HOW-TO Set Up and Process Your First Square Payment [COMING SOON]


PayPal has by far been around the longest in our trio, but the company's history and offerings have changed over time. In the beginning, PayPal was the primary payment processor for eBay - offering sellers and customers a way to securely exchange money over the internet without sending too much personal information.

However, PayPal has since expanded to include a number of payment features that compete with Square. PayPal now has online invoicing and eCommerce tools, and the platform also integrates with Venmo to even further expand the cashless money possibilities.

PayPal also offers the advantage of additional ancillary features you may need to run your business - printing shipping labels, providing debit cards and even business loans to expand your company. While Square does offer some ancillary features, PayPal has the advantage that their platform is more integrated across the web. If you're looking for a pure online payment processor, PayPal is probably the place to go.

PayPal offers many personal money transfer services as well, so many customers may be more inclined to use PayPal because they can pay with money already in their account.

However, there's no question that PayPal lags behind the other two options when it comes to in-person point of sale.

PayPal - for every transaction processed in-person through PayPal, you pay 2.7% of the transaction; for every transaction processed online through PayPal, you pay a $0.30 flat fee + 2.9% of the transaction; point of sale hardware costs from $25 to $500 depending on device(s)

HOW-TO Set Up and Process Your First PayPal Payment [COMING SOON]


Clover was started around the same time as Square, but from the beginning, they were focused on building a better, modern cash register. It took the company 4 years to ship their first product - the Clover Station - but the sleek design and simple-to-use features made Clover a quick hit.

The company has continued to innovate in the physical point of sale space, now offering a wide variety of both fixed-station and mobile payment processing devices. Some of these devices can get expensive, but to date, there have been more Clover POS devices sold than Square - and sales don't lie.

Clover was also early in releasing their developers platform - allowing outside coders to build additional tools that work seamlessly on the Clover devices. Clover actually runs on the same Android operation system that powers over 75% of smartphones worldwide - meaning it was very easy for developers to use their platform. There are now a proliferation of Clover-endorsed apps to manage promos, rewards, staff shifts, dining guest management, and more.

If you want arguably the best modern point of sale devices for in-person sales, it's hard to argue with Clover's proven successes. Clover does not, however, have any online or eCommerce invoicing/billing options - so you'll have to turn to one of the other options if you need to process payments over the internet.

Clover - for every transaction processed in-person through Clover, you pay a $0.10 flat fee + 2.3% of the transaction; point of sale hardware costs from $70 to $1750 depending on device(s), payment plans offered

HOW-TO Set Up and Process Your First Clover Payment [COMING SOON]

Confused? Questions? Just ask!

Ready to move on to step 3? Check out our next software guide: Workload Management.

nerd out,