You're not alone. Many businesses start with a point of sale provider that works great for a small business. Then they find, as they mature and grow, that they have needs the POS can't match.
Here are some great examples of when you should start shopping for a new POS:
Many systems make this complicated or impossible. Designed when online shopping was new, they haven't kept current. Many companies such as Lightspeed and Vend POS, offer e-commerce websites as part of their platform. This allows the flow of business to stay fast paced.
Other companies, like Accumula give you the online, and in store features of a big box retailer. Advanced features combine ERP, Ecommerce, and accounting functions, to deliver the ultimate in functionality.
Maybe you need membership or loyalty tracking. Maybe you need to be able to offer layaway. Maybe your POS doesn't offer gift cards.
Many basic POS systems lack the integrations you need to manage the business you have. Many POS companies sell their programs as solutions to every problem. Then after having the system for a while, you realize it wasn't meant for your restaurant or store. But often times it's too late, and you need to make due.
Also, your POS may have a bunch of features you'll never use. That's just another sign that your POS wasn't built with your business in mind.
We all went through the EMV compliance nightmare last year. But that aside, a POS company shouldn't be nickel-and-diming you to death over upgrades. POS Hardware isn't complicated, and software should include upgrades if you're paying them monthly.
The cornerstone of an effective POS system, is the reporting features. Without the advanced tracking features you need, you might as well be using a cash register.
Does your business need to track employee time cards? Does it need to track your inventory in several locations? Maybe you need to be able to track promotions, coupons, or gift cards?
Regardless of what you need to track, make sure your system tracks what you need. Even the most powerful system is worthless if it can't give you the data you need.
Whether it's tech support, or just someone to walk you through how to run payroll. Support is important to a business owner. Poor support keeps you on the phone longer. Which keeps you from doing what you do best, helping your own customers.
A good POS company will have 7 day per week support. Many offer 24/7 support. While 'round the clock support isn't crucial, you want to make sure someone is actually available when you call the 800 number.
Also important to me, is that the customer service is US Based, and well trained. Waiting on hold for 30 minutes because the operator has no idea how to fix your problem, is not a good feeling. Likewise dealing with a language barrier can add frustration to an already frustrating day. Let's face it, you're probably not going to be in a great mood when you call customer support.
That's a much easier list!
Features are always the most important. Because if you get POS cheap, but it doesn't have the features you need, you're back in the same boat as before! Make sure you get what you want. There are hundreds of POS companies. Someone has to make what you need.
Price of course, is always a close second to features. Don't pay more than you have to. When I started in this industry, I sold Microsoft Dynamics POS. That had astonishingly large setup costs, and upgrades. Now you can get into a POS like Vend or Lightspeed for less than $100 a month! So find something that does what you need, but fits your budget.
When you switch, make sure you check hardware compatibility. Your business already has POS hardware. Find a system that will use the hardware you already have! No reason to buy hardware you already have all over again. A barcode scanner is a barcode scanner, don't reinvent the wheel.
Data Migration is the one thing you might have to live without. I work with a few companies that offer it. And it's a treat. They'll take your existing product data, and move it into your new system. So you don't have to go through, and set up new SKU numbers for everything. That said, it's not always possible. But data migration is great when it's available.
Make sure you talk to a few different people for viewpoints before you make decisions. It's the POS company's job to talk you in to their software.
My Dad would always go to buy a car, and just buy whichever car he looked at first, because he'd be tired of looking. Don't be like that. Be a savvy consumer. Get opinions.
Also, feel free to shoot me an email. I'll be happy to give you some free POS advice anytime.