How to Choose the Right POS System for Your Business

Advice from a retailer who got frustrated enough to build his own.

Choosing a Point of Sale system sounds straightforward.

Compare features. Compare prices. Watch a few demos. Make sure it handles inventory and payments. Pick one.

After more than 35 years in retail, I believe that's the wrong way to choose a POS.

I've personally used or evaluated systems including Lightspeed, Shopify POS, Square and MultiFlex. Some were better than others. All could process transactions.

But eventually I realized something:

Processing the sale is the easiest part.

Almost every established POS system can scan an item, accept payment, process a return and print a receipt.

The question retailers should be asking is:

What is this system going to do for my business when there isn't a customer standing at the cash register?

That's where the differences become enormous.

It's also one of the reasons we eventually built PerfectPOS .

PerfectPOS didn't start because I woke up one morning and decided the world needed another POS system. It came from years of operating retail stores and repeatedly thinking:

Why doesn't my POS do this?

Here are the lessons I've learned—and what I believe every retailer should consider before choosing their next POS system.

1. Start With Your Business, Not the POS Company's Feature List

One of the most important things I would tell my younger self is simple:

Choose a system built by people who understand the business you're actually in.

Different businesses have very different operational requirements.

A café, clothing store, furniture retailer, sporting-goods store and service business may all need to accept payments—but that's about where the similarities end.

In apparel, for example, we're dealing with styles, colors, sizes, brands, seasons, suppliers, purchase orders, transfers, markdowns, layaways and constantly changing inventory.

That was one of my biggest problems when testing Square. It could process transactions, but I found it far too basic for the way we operate an apparel business.

Shopify POS was also relatively basic from my perspective. And after speaking with other Shopify users, I found that many had added multiple paid apps to get functionality they needed.

Lightspeed had considerably more functionality, but I found it complicated and still didn't give me many of the tools I wanted to actually help grow the business.

MultiFlex served us reasonably well for years, but eventually we outgrew it. Getting improvements made could also be expensive and painfully slow.

Key takeaway Don't ask only whether a POS can run your store today. Ask whether it understands where your store needs to go tomorrow.

2. Don't Confuse a Cheap POS With a Low-Cost POS

Price matters.

Of course it does.

But I've learned not to make the monthly subscription price the primary decision.

Suppose POS A costs $100 per month and POS B costs $250.

POS A appears dramatically cheaper.

But what happens when POS A also requires:

An email marketing platform An SMS platform A loyalty platform Additional ecommerce apps Reporting tools Inventory tools Employee scheduling software

Suddenly the $100 POS isn't really costing $100.

And that's before considering the cost of your time.

This became apparent to us when we built email and SMS directly into PerfectPOS. We could eliminate separate software subscriptions because the POS itself could communicate with our customers.

But the bigger advantage wasn't just eliminating another bill.

The marketing system could now work directly from our live POS data.

That changed everything.

Don't ask, "How much does the POS cost?" Ask, "What is my total technology stack going to cost after I buy this POS?"

3. Your POS Should Use Your Data—not Just Store It

This may be the biggest lesson I've learned.

Our old systems weren't necessarily doing anything wrong.

They processed sales.

They tracked inventory.

They generated reports.

For years, I didn't realize how much more they could have been doing.

I didn't know what I didn't know.

We would generate reports, export data, manipulate spreadsheets and then import information into completely different systems.

Our email platform didn't really know what was happening inside the store.

Our SMS platform didn't know.

Our ecommerce platform didn't know.

The information existed—but the systems weren't intelligently acting on it.

A modern POS should do more Your POS shouldn't just be a database. It should be an operating system for your retail business.

4. Ask What the POS Can Automate

We're operating businesses in an age of AI and automation.

If a POS still requires you to manually perform every action, I think that's a serious limitation.

At PerfectPOS, we've focused heavily on what I call:

Set It and Forget It.

Here's a simple example.

Suppose we mark down a product.

Traditionally, we'd change the price and perhaps create an email campaign promoting the markdown.

But the POS already knows which customers purchased similar merchandise.

Why shouldn't it do something with that information?

PerfectPOS can automatically identify relevant customers and notify them about the markdown.

That's what I mean by automation.

The retailer shouldn't have to:

Export a report → build a spreadsheet → import a list → create a campaign → send the message.

The event happens, the system recognizes the opportunity, and the appropriate action can happen automatically.

That's what retailers should be demanding from modern software.

5. Look Beyond Inventory Counts

Ask most POS companies about inventory management and they'll tell you they track inventory.

That's no longer enough.

Knowing that you own 17 units of something doesn't necessarily help you make a decision.

A better system should help answer: What should I do about those 17 units?

Inventory Aging

We can identify aging merchandise and then create actions around it.

Maybe the product needs to be:

Marked down Promoted Featured online Moved to another location

Those actions can become tasks assigned directly to employees inside the POS.

Now an inventory-aging report isn't simply something an owner looks at.

It becomes a workflow.

Multi-Location Inventory Optimization

Another problem is having the right merchandise in the wrong store.

If one location is selling a particular product significantly faster than another, the system should help identify that opportunity and prepare transfer recommendations.

The objective isn't simply knowing where the inventory is.

The objective is putting inventory where it has the greatest chance of selling.

6. Ask One Question Most Retailers Never Think to Ask

Can the system tell me which inventory I own that isn't listed on my website?

This became a huge issue for us.

We had merchandise sitting physically inside our stores that wasn't available for customers to purchase online.

Think about what that means.

We had already:

Purchased the inventory Paid for it Received it Stored it

Yet thousands of potential online customers couldn't even see it.

That's inventory you're carrying without giving it the maximum opportunity to sell.

PerfectPOS now allows us to identify inventory that's physically on hand but missing from our ecommerce website.

For us, that's an incredibly valuable report.

Look for the problems the system identifies that you didn't even realize you had.

7. Your Customer Database Is Worthless If You Don't Use It

I believe retailers make two major mistakes with customer information.

They either don't collect it—or they collect it and do nothing with it.

Your POS should make collecting customer information at checkout easy.

But then it should help you actually use that information.

Inside PerfectPOS, we can tag customers and create highly targeted segments.

For example, we can create tags based on clothing brands customers purchase.

Now imagine we've received a new collection of men's Diesel jeans.

We can communicate specifically with customers likely to care about that merchandise.

Compare that with blasting the same message to everyone in the database.

If I send a customer an email saying:

New men's Diesel jeans just arrived.

...and that customer is a woman who has never purchased men's clothing or Diesel, I've wasted an opportunity to communicate with her.

Worse, if I repeatedly send irrelevant messages, eventually she stops paying attention to all of them.

More marketing isn't necessarily better marketing. More relevant marketing is.

8. Customer Intelligence Should Reach the Sales Floor

Customer information becomes even more valuable when it's available during the transaction.

When one of our salespeople adds an existing customer to a transaction in PerfectPOS, Customer Intelligence can immediately surface useful information such as:

What the customer purchased previously Brands they purchase Contact information Birthday Customer information and history AI-generated selling suggestions

The salesperson shouldn't have to open five screens and analyze a customer report.

The intelligence needs to appear where and when it's useful.

The traditional POS records what the salesperson does. The next generation of POS should help the salesperson do it better.

9. Pay Attention to the Little Things

Every POS demo shows you how quickly the system can complete a transaction.

That's important.

A salesperson should be able to find inventory—even when an item has lost its tag—and complete a transaction with as few clicks as possible.

But most mature POS systems can handle basic checkout reasonably well.

It's the little operational details that often reveal whether the people who designed the software have actually worked in retail.

Here's one tiny example from PerfectPOS.

We offer layaways.

Staff need to follow up with customers who have outstanding layaways.

So when an employee contacts a customer, they can click a call button directly from the layaway screen.

PerfectPOS records the date and time of the contact.

When another employee looks at that layaway later, they immediately know when the customer was last contacted.

It's a small feature.

It will probably never headline a POS advertisement.

But if you've actually managed a retail store, you immediately understand why it's useful.

Ask vendors to show you the little things.

10. Your POS Should Help You Buy Better

Inventory is usually one of a retailer's largest investments.

Yet purchasing is an area where many POS systems provide surprisingly little assistance.

Open-to-Buy was a major problem for us.

We previously spent thousands of dollars per month getting the kind of Open-to-Buy information we needed.

We ultimately built those capabilities into PerfectPOS.

AI Purchase Order Import

PerfectPOS can import purchase orders directly rather than requiring someone to manually enter all that information.

That's my definition of useful AI.

It removes work.

The Buyer's Assistant

During buying season, we may visit many different suppliers over several months.

Historically, this created a problem.

You'd buy something from one supplier and weeks later see something similar somewhere else.

You don't necessarily remember everything you've already ordered.

Suddenly you've bought multiple versions of essentially the same product.

PerfectPOS's Buyer's Assistant gives us a visual view of merchandise we've already purchased.

Now when we're buying, we can actually see what's already coming.

That helps reduce duplicate purchasing and gives us a better view of the overall merchandising mix.

When someone tells you their POS has AI, ask: “Show me exactly how your AI saves me time, makes me money or prevents me from making an expensive mistake.”

11. Evaluate the Company Behind the Software

This is something I underestimated earlier in my career.

You're not only buying software.

You're entering into a relationship with the company building it.

With previous systems, I would regularly suggest improvements.

Sometimes the requests seemed to fall on deaf ears.

Other times we'd be quoted substantial amounts of money for relatively small changes and told development could take months.

That's frustrating when you're actually operating stores and can clearly see a better way of doing something.

Questions I would ask a POS company today: How quickly is the platform improving? Do they listen to retailers? Do the people building the product understand why you're asking for something? What significant features have they released during the last 12 months? What happens when customers suggest improvements?

Software isn't a finished product anymore.

The quality of the development team—and their willingness to listen—can be just as important as the features available today.

12. Don't Buy a POS. Buy a Better Way to Run Your Business.

If I were choosing a POS again today, my checklist would look very different than it did years ago.

Yes, I'd make sure checkout was fast.

Yes, I'd evaluate inventory management.

Yes, I'd compare pricing.

But those would just be the beginning.

Does this company understand my type of business? How much manual work can the system eliminate? Does it intelligently use my live data? What other software subscriptions can it replace? Can it help me buy better? Can it identify aging or misplaced inventory? Can it uncover inventory I'm not selling online? Can it help my salespeople sell more intelligently? Can it automatically turn customer data into targeted marketing? Does its AI actually accomplish something useful? Will the platform continue evolving? Does this system simply record my business—or does it help me run a better one?

That last question is the one I wish I'd asked years ago.

Why We Built PerfectPOS

Eventually, years of frustrations and ideas turned into something bigger.

Instead of continuing to ask other POS companies to build the tools we wanted, we built them ourselves.

That's how PerfectPOS evolved.

It wasn't designed by people trying to imagine what retailers might need.

It was built around problems we experienced running actual retail stores.

Built for Retailers, by Retailers.

We're continuing to build toward something I believe goes beyond the traditional definition of Point of Sale.

A platform where sales, inventory, purchasing, customers, marketing, ecommerce, employees, reporting, automation and AI work together using the same live retail data.

I think of it less as another POS and more as an AI-powered Retail Operating System.

Because after decades in this business, I've learned that the best technology doesn't simply tell you what happened yesterday.

It helps you decide what to do tomorrow—and increasingly, it should be able to take care of some of those actions for you.

Don't choose the system that can process your next transaction. Choose the system that can help you build a better retail business.

PerfectPOS — Built for Retailers, by Retailers.

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