A point-of-sale system is more than a cash register with a screen. It decides how fast your counter moves, whether your stock count is right at the end of the month, and how much time you spend on paperwork. Picking the wrong one is expensive because switching later means re-entering products, retraining staff and losing history. This guide walks through the questions worth answering before you buy, with a focus on what matters for shops in Jamaica and the wider Caribbean.
1. Start with how your counter actually works
Before comparing features, write down what happens at your counter on a busy day. A mini-mart that sells hundreds of low-value items needs fast scanning and quick cash handling. A hardware store needs to find parts by name or number and often sells by the case. A restaurant needs tables, a kitchen ticket and split bills. A barbershop needs appointments and commission. The best POS for one of these is often a poor fit for another.
A useful exercise is to list your ten most common transactions and your three most awkward ones. The awkward ones decide whether a system works for you: a customer paying part in cash and part by card, a return without a receipt, a sale in US dollars with change given in Jamaican dollars, or a staff member selling on credit to a regular customer.
2. Plan for unreliable internet and power
Many POS systems are cloud-only: if the connection drops, the till stops. In places where outages and slow connections are part of normal business life, that is a serious risk. Ask every vendor one direct question: what happens to a sale when the internet goes down in the middle of it?
Good answers include an offline mode that stores sales on the device and uploads them when the connection returns. Weak answers include "it rarely happens" or "use a hotspot". Also think about power: a laptop or tablet with a charged battery keeps a counter running through a short outage, while a desktop without a UPS does not. We cover offline operation in detail in Offline POS explained.
3. Check currency and payment handling
If you serve tourists or deal in US dollars, check exactly how the system handles a second currency. Questions to ask:
- Can a customer pay in USD for a sale priced in JMD, and does the system calculate change correctly?
- Where is the exchange rate set, and who can change it?
- Can one sale be split across cash, card and another method?
- Do receipts show the currency and rate used, so a customer can check the maths?
- Are tips recorded separately from sales, so they are not counted as revenue?
These details look small until month-end, when unclear records make reconciling cash and card totals slow and error-prone.
4. Think about tax and records early
Your POS produces the records your accountant works from. Make sure you can set up the taxes that apply to your business (for most Jamaican businesses that means understanding how General Consumption Tax applies to what you sell), print clear receipts, and export sales reports. Tax rules change, and different goods and services can be treated differently, so confirm your setup with your accountant or with Tax Administration Jamaica rather than relying on a vendor's defaults.
Ask whether you can export your data in a standard format such as CSV. If the only way to see your history is inside the vendor's app, you depend on that vendor indefinitely.
5. Understand the full cost over several years
Price comparisons are often misleading because one system charges monthly and another charges once. Compare the total over the period you expect to use the system, usually three to five years, and include:
- Software fees: monthly subscriptions, per-terminal or per-user charges, and paid add-ons.
- Hosting, if the software runs on your own hosting account.
- Hardware: receipt printer, cash drawer, barcode scanner, tablet or laptop.
- Card processing fees, which are charged by the payment provider, not the POS.
- Your time for setup and training.
We work through a full example in Subscription vs one-time software.
6. Decide where your data should live
With cloud software, your sales and customer data live on the vendor's servers. With self-hosted software, they live on a hosting account you control. Neither is automatically better. Cloud software means someone else handles servers and updates. Self-hosted software means you keep control of your data and are not forced into price rises, but you are responsible for your hosting account and your backups (see A simple backup routine).
7. Test it with your own products and devices
A demo with sample products tells you little. Before you commit, try a realistic session:
- Enter ten of your real products, including one with sizes or colours.
- Ring up a normal sale, a split payment and a refund.
- Print a receipt on the printer you plan to use.
- Turn off Wi-Fi in the middle of a sale and see what happens.
- Run an end-of-day report and check that the totals match what you entered.
If anything in that list is confusing, your staff will find it confusing too.
8. Ask about support and updates
Find out how you get help when something goes wrong: email, phone, a contact form, or a community forum. Ask how updates are delivered and whether they cost extra. For a small business, a clear answer from a real person within a business day is worth more than a long feature list.
A short checklist
- Does it handle my awkward transactions, not just simple sales?
- Does it keep selling when the internet drops?
- Does it handle JMD and USD the way my customers pay?
- Can I export my sales and stock data?
- What will it cost in total over three to five years?
- Who controls my data, and who handles backups?
- Have I tested it with my own products, printer and staff?
Where CWPOS fits
We build CWPOS, a self-hosted point of sale with an offline mode, multi-currency payments, split payments and thermal receipts, sold as a one-time licence with source code. It is one option among many; whichever system you look at, the checklist above will help you compare them fairly. You can try the CWPOS demo with the steps from section 7.
