How to choose the best invoicing software for your business: questions to ask vendors

In this guide, a vendor is a company that sells invoicing software.

Why a sales demo is not enough

An invoicing demo shows a neat invoice sent in seconds. The problems show up later, for example:

• the invoice is missing a detail your country requires, such as a tax number or a sequential invoice number,
• online card payments carry a fee on top of the payment provider's fee,
• your accountant can't import the invoices into the accounting program they use.

So ask about these in writing, and ask every vendor exactly the same questions. Then you can compare their answers directly.

Before you contact any vendor

Write down your answers to these four points. They decide which questions in the checklist matter most to you.

• Where you and your clients are. Your country, your clients' countries, and the currencies and sales taxes you use.
• How you bill. One-off invoices, the same invoice every month, hours worked, or deposits or payments in stages.
• How you want to be paid. Bank transfer, card, or local payment methods.
• Who else needs the invoices. Your accountant, and the accounting program they use.

The checklist

The questions are in three groups. Must have means a problem here can delay your payments, break tax rules, or make it costly to leave. Nice to have means it makes a real difference for many people. Optional means it only matters to some people. When you open the checklist in NeutralPick, you can move any question to a different group to match your answers above.

• Must have
• Invoices your country acceptsOften required by lawDo invoices show everything my country requires, such as tax numbers and unbroken invoice numbering, and do you support e-invoicing where required?Rules differ by country, and some require electronic invoices in a set format. Ask your accountant what yours must show.
• Online payments, with fees you knowWhich payment methods can clients use, and what fees do you add on top of the payment provider's fees?Some tools add their own fee to every card payment. Add both fees to the price.
• Works with your accountantCan my accountant get the invoices and payments into their accounting program, by a direct connection or a standard file?Ask your accountant which format they need before you choose.
• You can keep your recordsCan I export all invoices as PDFs and data files at any time, including after I stop paying?Many countries require you to keep invoices for several years.
• Automatic remindersCan it send polite payment reminders automatically when an invoice is overdue, on a schedule I choose?Reminders are one of the simplest ways to get paid faster.
• Nice to have
• Recurring invoicesCan it send the same invoice automatically every week, month or year?Saves time if a client pays you a fixed fee every month, or for subscriptions.
• Other currencies and languagesCan I invoice in other currencies and languages, with the right tax wording for each client?Only matters if you have clients abroad.
• Quotes that become invoicesCan I send a quote or estimate and turn it into an invoice when accepted?Saves typing everything twice.
• Invoices that look like your businessCan I add my logo and adjust the layout, without the vendor's branding on the invoice?Some free plans add the vendor's name to your invoices.
• See who owes whatCan I quickly see which invoices are paid, due or overdue, and how much I'm owed in total?Helps you plan cash flow.
• Optional
• Bill for time and expensesCan I record hours and expenses and add them to an invoice?Only matters if you bill by time.
• Invoicing from your phoneCan I create and send invoices from a phone app?Useful if you finish jobs away from a desk.

Answers to look at carefully

Vendors often answer the points below in vague terms. When you get a vague answer, ask the follow-up question shown here. A vague answer often means the honest answer is "no" or "only partly".

• "Compliant invoices". Ask: compliant with which country's rules, and do you support e-invoicing where it's required?
• "Get paid online". Ask: what is your fee on each payment, on top of the payment provider's fee?
• "Free". Ask: what is left out, such as recurring invoices, your own branding or reminders?
• Leaving later. Ask: can we export every invoice and payment record, and for how long after we cancel?

What to do with the answers

1. Put all the vendors' answers side by side.
2. Look at the Must have questions first. If a vendor answers No to something you marked as a must-have, remove that vendor.
3. If a vendor answered "Partial" to a must-have, ask them exactly what is missing.
4. Show a sample invoice from each one left to your accountant before you choose.

Why use NeutralPick to compare invoicing software vendors

• Every vendor answers the same questions. Each vendor gets its own private link to your checklist and answers in writing, so you can compare their answers question by question.
• All the answers in one table. You see every vendor's answer to every question side by side, instead of searching through emails and call notes.
• No vendor can pay to influence it. There are no adverts, no paid placements and no "featured" vendors. No vendor can pay to be shown to you or placed higher.
• Free, with no account. You don't need to sign up or pay anything.

Start with this checklist See an example comparison