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How to Choose Invoicing Software

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small business invoicing software

So. You’ve decided that Excel and Word just aren’t cutting it anymore. Maybe, like FreshBooks founder Mike McDerment, you accidentally saved over an old invoice in Word and lost important data. Maybe you have trouble keeping track of which clients haven’t paid yet and you want an easier way to do it. Or maybe you just don’t like the look of your invoices and you want something a little more professional.

Whatever the case, there’s a huge variety of small business invoicing software out there to make your job easier. FreshBooks is by far the most commonly known, but there are a slew of other good options as well, and they are well worth a look. Which is the best invoicing software for you will depend in part on your business and your specific needs. And the first big question you’ll need to ask yourself is:

Invoicing or accounting?

Cloud-based accounting software has expanded to include nearly all aspects of invoicing software. Unless you need auto-billing (that is, the ability to automatically charge your clients’ credit cards after each invoice), there’s probably accounting software out there with all the invoicing features you need. The benefit to handling invoicing with accounting software is twofold. First, it allows you to perfectly integrate your invoicing and accounting. Second, in many cases you won’t pay much more for accounting software than you would for invoicing software. Depending on your current accounting solution, it’s at least worth considering.

So who should stick to invoicing software and ignore the accounting stuff? Probably anyone where any of the following points apply:

  • You already have accounting software you really like and it will integrate with most invoicing programs.
  • You want all the invoicing bells and whistles you can get.
  • You need auto-billing.
  • You’ve already checked out the accounting software options and none of them give you the invoicing features you need.

For anyone else, I’d recommend checking out accounting software first, paying special attention to invoicing-focused solutions like Zoho Books and FreeAgent. You can find a guide to choosing accounting software here.

Cloud-based or locally installed?

The rest of this article focuses on cloud-based solutions, but there are locally installed invoicing programs available. Cloud-based programs give you convenience, mobility, and secure data storage and backup. Locally installed programs can be cheaper in the long run (a one-time cost rather than subscription).

Free or paid?

If you need advanced features, you’ll have to pay for them. However, if you’re just looking for something basic, you may be able to get it for free. For more information about the pros and cons of free invoicing software, see the article here.

What invoicing software features do you need?

Your next step is to narrow the available options by figuring out what you really need. If you want every single invoicing feature available in stand-alone software, your choice is almost definitely Invoicera. Go check it out. If you need integrations with a lot of other software, take a look at FreshBooks – it offers more than any other program. But there’s no sense in paying for features you don’t need, and most businesses won’t need everything.

Make a list of the features you absolutely need, and then a second list of the perks you’d like – the icing on the cake. To help you brainstorm, here’s a list of some of the features available:

• Online payment option• Customizable templates• Estimates/quotes
• Recurring invoices• Automatic payment reminders• Client portal
• Attach files to invoices• Automatic receipts• Basic stock list
• Financial reports• Automated late fees• Customer statements
• Offer percentage discounts• Auto-billing• Multi-lingual
• Inventory tracking• Snail mail services• Multi-currency
• Time tracking• Expense tracking• Field for S&H or P&P
• Sales tax• Mobile apps• API

What are your options?

Now that you have your list, see how it lines up with available software. If you already had a program in mind, that’s a good place to start. So are the 3-star and up reviews here. You can either search reviews on this site for the features you want (use the search box in the upper right-hand corner) or do a Google search for the name of the software and the feature (for instance: “Freshbooks mobile”). You should be able to quickly pull together a list of 2-4 options.

Once you have a short list, read the reviews and see which programs look most appealing to you.

Try it out

Pick your favorite option thus far and embark on a free trial. Pay special attention to invoice templates and default email options. Some invoicing programs offer lots of template options and customizations. Others offer a single template with basically no options for customization. That’s fine if you like that template, but if you don’t, it may rule out the program straight off the bat.

If you like the templates, continue to explore, noting the look and feel of the program. Is it easy to navigate? Are there inefficiencies in setup that are going to cost you time? If you run into any questions, take the opportunity to test out customer support.


With luck, you’re loving the test run and you can’t wait to import all your info, customize your settings, and start using the new program. But if you feel less than enthusiastic, move on and try out the next program on your list. The right fit is probably out there.

Good luck! As always, don’t hesitate to contact us with any questions about small business invoicing software!

Katherine Miller

Katherine Miller

An itinerant wanderer, Katherine spent the past year in Colorado, Chicago, and New Zealand. Several years as an independent contractor have familiarized her with the headaches that often accompany small business accounting, and she’s made it her mission to find the best tools to make things a little easier for new entrepreneurs. When she’s not busy investigating the ins and outs of the latest accounting software, she can be found working on a novel, trekking up mountains, and training in Krav Maga. (Though usually not all at once.)
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