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How to Choose a Bookkeeping Software

How to Choose a Bookkeeping Software

Written by 
Pilot Team
April 4, 2019
How to Choose a Bookkeeping Software

Once upon a time, bookkeepers recorded their information using pen and paper, keeping a company’s books in specially designed ledgers. Computers have long since replaced such old-fashioned approaches to bookkeeping. In fact, there are a number of software platforms specifically designed for this purpose.

In order to choose the right bookkeeping software for your business, you’ll need to weigh a number of important factors. Careful consideration now will help you pick a software system that will last your business for years. Now, let’s jump into the important factors to consider.

A quick note: People often use the terms “accounting software” and “bookkeeping software” interchangeably. Most software programs used for bookkeeping include robust accounting tools, so it’s fair to use the words interchangeably. However, the two disciplines themselves are different.

Factor 1: Ease of Use

Time to Learn

While all software programs will require some time to master, certain programs are more intuitive than others. If the person who will be operating the system is a bookkeeping novice, choose a platform that’s both simple and includes support, like tutorials, guides, and live help. If you’re fortunate enough to have an experienced bookkeeper on staff, consider choosing a tool that they are already familiar with. This minimizes implementation hassles.


Access is another important usability factor. Cloud-based bookkeeping software allows you to log in from just about anywhere. In fact, many cloud-based platforms include apps that let you access your books from mobile devices. Desktop bookkeeping software, on the other hand, can only be accessed using the computer on which you’ve installed the software.


Some bookkeeping software packages limit the number of users who can access your books. If you’ve got multiple offices or external financial advisors, confirm that the bookkeeping software you’re considering will allow those people to set up accounts.

Factor 2: Bookkeeping Software Features

The size of your business, the types of products or services you sell, and your preferences for in-house versus third-party processing will all affect which features you’ll need from your bookkeeping software. Any decent bookkeeping program will support basic transactions, such as invoices and expenses.

Here’s a sampling of the more advanced features you might need from your bookkeeping software:

  • Payroll. If you have employees, someone will have to manage payroll processing. If you choose to have your bookkeeper manage your payroll, you’ll want a bookkeeping tool with robust payroll functionality. Another option is to manage payroll with a third-party tool that integrates with your bookkeeping software, like Gusto. That way all your info is recorded in one place.
  • Inventory. Businesses that sell physical products will definitely need some way to track and manage inventory. The ideal way to do so is to choose a bookkeeping platform with built-in inventory management support.
  • Subscriptions. Many service companies, particularly SaaS companies, sell their services through subscriptions. Such companies will definitely need a bookkeeping system that makes subscription management easy. For example, you’ll want a platform that will automatically generate invoices for your subscribers every month with a minimum of manual intervention needed.
  • Sales tax. Setting, collecting, tracking, and paying sales tax is complicated enough when you’re only selling in one jurisdiction. Companies that sell their products in multiple states, which include just about all e-commerce companies, will definitely need an excellent sales tax management system. A full-scale e-commerce company will likely need a separate sales tax software package. But be sure that your bookkeeping software can integrate with said package. Businesses with less complex sales tax situations may be able to get by with just bookkeeping software if it has a sufficiently robust built-in sales tax management system.

Factor 3: Scalability

Switching from one bookkeeping tool to another is often a logistical nightmare. That’s why it’s important to choose a bookkeeping software that will suit your business today and in the future. Consider your goals, and then decide what you’d need from your bookkeeping software to support those goals.

For example, if you plan to open offices across several different states, you’ll need a bookkeeping software platform with multi-state payroll support and access for enough users to support each of your offices.

Many of the better bookkeeping software packages come in different versions, each built on the same basic software program. As your business grows, you can quickly and easily upgrade your bookkeeping software to the next version when you need it. The beauty of this system is that you don’t need to pay for features you’re not using. But when you do need more advanced features, adding them is painless.

Factor 4: Compatibility

Unless you just launched your business yesterday, you probably already have an existing financial management structure. You probably have a business bank account or two, loans, credit cards, and perhaps even a CPA – even if you only speak to them at tax time.

It’s important to choose a bookkeeping software system that will integrate smoothly with your existing systems. This is particularly important if you have a CPA or other financial advisor and want to keep using them. You’ll make your life much easier if you choose a bookkeeping tool that matches whatever they’re using in their own office (or is at least something they’re familiar with).

Not sure whether you need to hire an accountant? Learn more here.

You’ll also need to consider what it will take to set up the new software solution. Some excellent bookkeeping software tools are so complex that they require sophisticated technical skills to get them up and running. If you don’t have a dedicated IT person, that means hiring someone to get it set up. And if you run into technical problems down the line, you’ll need to find an expert to solve them for you. On the other hand, if you do have an IT person who’s familiar with that complex software, it could be a great choice for you.

Factor 5: Price

By the time you finish going through all the above factors, you’ve probably narrowed your search down to just a few bookkeeping software options. At this point, it’s time to consider what your budget can stretch to include. Generally speaking, the more specialized the software and the more advanced the feature set, the more you can expect to pay for your bookkeeping software. You may end up needing to compromise on certain features to keep your software affordable.

For example, you might want to have the best inventory management software available, but find that the bookkeeping software with the most robust inventory management support is out of your price range. In that case, see if there are any other possibilities. Many bookkeeping software packages will integrate with numerous third-party apps. Perhaps you’d be better off choosing a bookkeeping software that doesn’t have great inventory management but that integrates with a solid inventory management app.

An Alternative Solution

Before you plunk down the money for a bookkeeping software system you are going to manage yourself, consider whether this is really the best use for your hard-earned dollars. Hiring Pilot to manage your bookkeeping can spare you the hassle of setting up and maintaining your own bookkeeping system.

Pilot uses industry-standard tool QuickBooks Online to manage our clients’ books. Combine that with having your own dedicated account manager, and it’s the best of both worlds.

You don’t have to worry about managing the books yourself or finding and employing an in-house bookkeeper, as you’re getting a robust bookkeeping software system and a terrific bookkeeper all in one easy-to-use service.

At Pilot, we have a team of expert bookkeepers using unique tools to streamline your bookkeeping. If you want to keep better books,try Pilot.

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