What to ask a delivery software vendor before you sign

Choosing delivery software has an asymmetry problem: the vendor has had that conversation hundreds of times and you will have it once or twice in your life. The demo is prepared, the data is clean, nothing breaks.

There is nothing wrong with that, it is what anyone selling does. But it means the useful questions are not the ones a vendor will answer unprompted. These are the ones worth asking.

About your customers

1. Do my customers have to install anything?

First and most important. If your customer has to download an app, register and remember a password just to place an order, adoption will be low. It does not matter how good the system is. People do not install an app to buy something twice a week.

2. What happens with the customer who refuses to use anything new?

There is always a percentage who will keep phoning. Ask how that order gets entered and whether it ends up in the same place as the rest. A system that only works for digital customers leaves you running two systems in parallel, which is worse than running one.

About the operation

3. What happens when the driver loses signal?

Every delivery area has dead zones. Ask whether the driver app keeps working offline and what happens when the signal returns. If the answer is that it needs a permanent connection, it will fail on day one in a basement or a rural stretch.

4. How is an order handled if it arrives after the driver has left?

This happens daily. What you need to understand is whether that order can be added to the route in progress or whether it waits until tomorrow.

5. How is a failed delivery recorded?

Nobody home, no answer, goods refused. If the system only covers the happy path, everything outside it will end up being resolved over WhatsApp between you and the driver, outside the system.

6. Does it handle returnable containers or goods coming back?

If your business runs on containers, this is not a detail. You need to know how many each customer is holding. Plenty of generic delivery systems do not cover it, because they were built for parcels.

About the money

7. How is the service charged: per driver, per order, or flat?

Each model suits a different situation. Per order scales with your volume, which is fine starting out and can hurt as you grow. Per driver is predictable but punishes seasonality. Ask them to project the cost using your peak season volume, not your average.

8. What happens if I exceed the plan limit?

Ask specifically whether service is cut off, whether overage is billed, and how much that overage is. Service being cut mid-round is a serious problem.

9. Is there a setup or onboarding fee?

And if so, what exactly it covers. Loading the initial customer and product base is usually the heaviest part of any migration.

10. Does it support customer accounts and credit terms?

If you sell to shops or have customers who pay monthly, you need a balance per customer and a record of partial payments. A system that assumes every delivery is paid on the spot will not work for you.

About afterwards

11. How do I take my data with me if I leave?

Customers, orders, history. In what format, how often and at what cost. The answer tells you a lot about how you will be treated as a customer once you have already signed.

12. Who answers when something breaks on a Saturday morning?

Delivery operations do not run nine to five, Monday to Friday. Ask the real support hours and the channel. If support is email only with a 48 hour response, know that in advance rather than on the Saturday.

One warning sign

If the answer to several of these is "we can look at that later" or "it can be custom built", treat it as data. It does not always mean the feature does not exist, but it does mean it is not solved today, and today is what you will be operating with.

The best answer to any of these twelve questions is a demonstration on screen. If they can show it working, it exists.