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PaySimple vs Square Point of Sale Comparison (2026)

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Good recommendations?

PaySimple

Square Point of Sale

Overview

PaySimple is the leading payments management solution for service-based businesses, powering the cashflow of over 20,000 companies nationwide.

Square Point of Sale is the customizable point-of-sale system built for businesses of all shapes and sizes.

Platforms supported

Web-based
iPhone app
Android app
Windows Phone app

Typical customers

Freelancers
Small businesses
Mid size businesses
Large enterprises

Customer support

Phone
Online
Knowledge base
Video tutorials

view more detailsview details

Platforms supported

Web-based
iPhone app
Android app
Windows Phone app

Typical customers

Freelancers
Small businesses
Mid size businesses
Large enterprises

Customer support

Phone
Online
Knowledge base
Video tutorials

view more detailsview details

Video & Screenshots

Pricing

Starting from

69.95

Per month

Free trial available
Credit cardless trial
Free account
Subscription based

Starting from

Per month

Free trial available
Credit cardless trial
Free account
Subscription based

User reviews

4.5

298

196

Value for money

Ease of use

Features

Customer support

73%

would recommend this app

4.6

2.2K

614

130

Value for money

Ease of use

Features

Customer support

83%

would recommend this app

Pros

“Not every invoice but every weekly invoicing batch has more than one invoice that is off a penny in either direction.”

Mel G.

Office Manager

“We've been using this system for years after an accountant switch and if I could convince the boss to switch to something else, I would.”

Mel G.

Office Manager

“It simplifies invoicing, recurring billing, and online payments, which has streamlined my business operations significantly.”

Aastha G.

Process associate

Pros

“I can use it to check people out, keep people engaged and communicating, process payments professionally and easily and the website was a big bonus!”

Shawn H.

Lead Therapist, Owner

“It offers a debit card tied to the account, that allows me to have instant access to funds, and if I use the transfer option, it takes one day to reach my bank account, or instant for another fee.”

Chris L.

Operations

“Square Point of Sale is highly effective for a music and content-based business that sells lessons or services, as it makes in-person and online payments simple and fast.”

Michael Z.

Owner

Cons

“At this point, we've sent multiple unanswered notices asking about fees, formally cancelling the service, and still we've never received an invoice, only continual withdrawals from a bank account until we closed it.”

Monica V.

Owner

“I have been using the product for over 15 years now and it's hard to connect to Customer Representative and if we open a ticket, they take 4-5 days to reply and without proper resolution.”

Praveen C.

President

“We also started receiving requests for payment from their vendor/partner (it's unclear) named PaySafe who threatened to send us to collections despite acknowledging that we've received no services from them.”

Monica V.

Owner

Cons

“The setup process was confusing as it required an another app epically if you were using the lighting reader and a verification process, as well as linking your bank accounts and test transactions.”

Absana P.

Tier III Technician

“This situation caused real damage to my life. That $1,447 was reserved for something extremely important with a strict deadline attached to it. Because I did not receive the money in time, I am now facing serious financial consequences and problems with institutions that were expecting that payment.”