Choosing a point-of-sale system feels overwhelming. There are dozens of options, every vendor promises the world, and the wrong choice can cost you months of pain and thousands of dollars to undo.
Here's what actually matters — and what to ignore.
The questions that matter most
Before looking at any specific system, answer these:
How complex is your menu or inventory? A coffee shop with 20 items has very different needs than a restaurant with modifiers, combos, and a kitchen display system. Retail stores with hundreds of SKUs need robust inventory tracking.
Do you need table management? Full-service restaurants need table layouts, course management, and split bills. Quick service and retail don't.
What reporting do you actually need? Some owners need detailed sales-by-item reports. Others just need daily totals. Don't pay for reporting you'll never use.
What's your internet situation? Some POS systems require constant internet connectivity. If your connection is unreliable, you need a system that works offline.
The main options in 2026
Square is the easiest to get started with. Hardware is affordable, setup is fast, and the free tier covers basic needs. It works well for simple retail and food service. Limitations show when you need advanced inventory or kitchen integrations.
Toast is built specifically for restaurants. It handles complex menus, kitchen display systems, and delivery integrations well. It's more expensive and requires a contract, but it's the right tool for full-service restaurants.
Lightspeed is strong for retail, especially businesses with large inventories, multiple locations, or e-commerce integration needs.
Clover is flexible and has a large app marketplace, but costs add up quickly once you start adding features.
What we recommend for most Winnipeg small businesses
For most restaurants and cafes: Square for Restaurants or Toast, depending on complexity.
For most retail: Square for Retail or Lightspeed.
The most important thing isn't which system you pick — it's that you get it set up properly. A good POS system configured badly will cause more problems than a simpler system configured well.
That's where we come in. Dexabyte handles POS setup, configuration, staff training, and ongoing support for Winnipeg businesses. Get in touch if you're evaluating options or need help with an existing system.