Billing Software Buyer's Checklist: Questions to Ask First

Most people buy billing software after one demo, one price quote, and one friend's recommendation. Then six months in they find out that the report they needed does not exist, or that getting their data out costs extra.

This checklist is meant to be used live, with a pen, during the demo. We built it from the questions we wish customers asked us earlier. Skip any that do not apply, and do not be shy about the awkward ones.

Start with your own list, not theirs

Before you see any demo, write down what you do in a normal week. How many bills a day? Do you sell at a counter, send invoices to customers, or both? Do you track stock? Do you buy on credit and sell on credit? How many people will use it?

Then mark three things you cannot live without. A vendor's twenty impressive features do not matter if the three you need are weak. Put those three on a card and test them yourself during the demo, with your own examples, not their canned data.

Questions about daily work

• Can I create an invoice, a quotation and a delivery challan, and turn one into the next without retyping?
• Is there a counter or POS screen, and is it fast enough for a queue?
• How does it handle sales returns and credit notes?
• Does stock update when I sell and when I buy? Can I see low-stock items?
• Can I see who owes me, how much, and for how long?
• Can I handle my sales in rupees and my customers' preferred language?

Ask them to show it, not tell you. 'Yes, we do that' is cheap. A two-minute live walkthrough is not.

Questions about things the brochure skips

This is where products differ most, and where they are most often unclear. Never assume. Ask directly about each of these and get answers in writing.

• GST and e-invoicing: does it generate tax invoices in the format you need? Does it file returns or connect to government portals, or do you still do that elsewhere? Confirm with your CA what you require.
• Barcode scanners and printers: which devices work, and has the vendor tested them?
• Payment gateways: can customers pay online from an invoice, or is it record-keeping only?
• Mobile access: is there an app, or only a browser?
• Accounting exports: can your accountant get data in a form they can use?

Billing tools differ here, ours included. Billy, for example, does not do GST filing or e-invoicing, and we'd rather you hear that now than discover it later.

Questions about your data

Your invoices, customers and stock history are the real asset. The software is replaceable. Your data is not.

1. 1Where is my data stored, and who can access it? (See our security checklist.)
2. 2How often is it backed up, and have restores been tested?
3. 3Can I export my data myself, in what formats, and is it complete? (More in backing up and exporting your billing data.)
4. 4If I cancel, what happens to my data, and for how long can I still download it?
5. 5Can I import my existing customers and products, or must I retype them?

Questions about money and exit

Get the whole price in one place. Is it monthly, yearly or one-time? Are there charges per user, per business, per invoice or per branch? What does the second business cost? What happens at renewal: does the price change?

Ask about the trial. A free period with your real data is far more useful than a demo. Ask about refunds, too, and what the notice period is. If you cannot find these answers on paper, assume they are not in your favour.

Questions about people

Software is a relationship with a support team. Ask how you reach them, in which languages, during what hours, and whether you speak to someone who understands accounting or just reads a script. Ask what a typical fix takes, and whether updates arrive automatically.

Also ask about training. A tool your staff will not use is worth nothing. Our post on training staff on new billing software covers what a decent rollout looks like.

Scoring it honestly

After each demo, rate the vendor from one to five on your three must-haves, data safety, price clarity, and support. Do it the same evening, while impressions are fresh. If two products tie, pick the one whose people answered the awkward questions best.

If you want to see how we answer them, book a conversation and bring this list. And if you are still deciding between a sheet, a desktop tool and a cloud one, start with that comparison. Already chosen? Moving from Excel without losing data is the next read.