Best Billing & Invoice Software 2019

Mark Pickavance ·
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One of the best ways to manage your business’s cash flow is to have an effective invoicing program. Beyond creating professional-looking, easy-to-understand invoices, the best applications can help you handle complex invoicing problems. Look for software that includes an email component, automated reminders and payment tracking so all parties know the exact state of an account at any given time.

Best for Teamwork


FreshBooks is a slick online accountancy solution that has grown in popularity over the past few years – an estimated 5 million businesses currently use this product. This is because of its accessibility, flexibility and affordability make it a useful tool for sole proprietors and small businesses. Other than being easy to configure and use, FreshBook’s other major selling point is it has collaboration at its heart. This makes it ideal for teams of people working on projects who need to turn their efforts into income efficiently. The software’s collaboration tools can even extend out to vendors and clients, so no one is blindsided by a bill they’re not expecting or haven’t correctly budgeted for. The software also has extensive automation features. For example, it can automatically send out regular invoices to customers at the right time and alerts you when payments are overdue. However, FreshBooks doesn’t have an inventory management component. As such, it isn’t suitable for people who exclusively sell physical products or who bundle them with other services.
  • Great team collaboration tools
  • Handles multiple businesses
  • No inventory tools
  • Support only available during business hours
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Best Budget Software


Xero is a cloud-based double-entry accountancy system that incorporates sales, inventory control, purchase orders, payroll and invoicing in one place. It even has a fixed asset register, in case you need one. What’s great about Xero is you get this functionality for a relatively modest monthly price. There are three plans: Early, Growing and Established. The Early plan costs $9 a month. It doesn’t have payroll and limits you to five invoices, quotes and bills. The Growing plan costs $30 a month, and it takes the limits off invoicing and adds payroll for five employees. The Established plan costs $60 a month, and it extends the payroll to 10 employees and allows you to handle multiple currencies in your invoices. All the plans have optional extras. For example, for a few dollars more, you can extend the number of employees, track expenses or add payroll to the Early plan. As such, you can tailor Xero to your needs and keep costs manageable. One downside to Xero is its service doesn’t have any means to backup, which is a prerequisite for those who need full auditing and record retention.
  • Total accountancy solution
  • Full inventory control
  • Affordable
  • Payroll feature doesn’t work for all states
  • No backup
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Best for a Growing Business

Intuit QuickBooks Online

With its QuickBooks brand, Intuit has a massive slice of the accountancy software market for small and medium-size businesses. QuickBooks Online is a web-based option for those who want a flexible accountancy solution with bank reconciliation, expense tracking, invoice generation and financial reporting. The invoicing component lets you customize templates, create rules for emailed payment reminders and acknowledge payment. There are four basic plans: Simple Start, Essentials, Plus and Self-Employed. You can add self-service or full-service payroll functionality to the plans if you want to create a complete fiscal pathway that includes the business, vendors and employees. All the plans can invoice, accept payments and send estimates, but you need Essentials or higher to manage bills and use the time-management feature. Further, you need the top Plus plan to isolate multiple projects and manage contractors. The main complaint about QuickBooks is it is so expensive, but the company has been addressing that problem. It may be time to look again at this very popular solution.
  • Easy to switch or cancel plan
  • Online and desktop apps
  • May intimidate new users
  • Track record of annual price increases
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Best for Managing Cash Flow

SAGE Intacct

U.K.-based company Sage has a wide range of accounting programs that cover every size of business, and Sage Intacct is its cloud-based solution. It is a full-featured suite that covers purchasing, order management, accounts receivable, cash management and reporting. It also incorporates collaboration tools so teams and departments can coordinate their efforts. The invoicing side of Intacct is nested inside accounts receivable and provides a single view of quotes, sales orders and invoices. It automates the process of invoicing, allowing accounting staff to better use their time. To further reduce the workload, the software automatically posts order transactions to your general ledger and accounts receivable ledger. This lets you see a real-time view of income flow. Sage Intacct’s primary objective is to achieve healthier cash flows by shortening invoice and payment cycles to optimal levels. Intacct’s biggest weakness is its report builder can be difficult to use – it was clearly built by programmers and not accountants. As such, it may be worth the investment to hire a contract worker to create custom reports once you are up and running.
  • Very flexible
  • Constantly enhanced
  • Report writing is complex
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Best for Retail Businesses


Square is the preferred solution of retail businesses that need a solid POS and the ability to take credit card and contactless payments. As with everything Square does, the invoicing part of its product is remarkably straightforward to configure and use. To create an invoice, you just input the customer's email, a description of the product or services, and the amount to invoice. You can then send it using the POS app or Square Dashboard. The program lets you create custom invoice layouts, set automatic payment reminders, accept online payments, and track invoices and their payment statuses. For those that need them, you can even attach additional documentation and receipts. It’s also flexible enough to handle one-time payments, returning clients and repeat business. And, it connects to Square Capital, an associated financing package for those who want to pay in installments for big-ticket items. Square doesn’t charge a monthly fee for invoicing, although it charges a fee of 2.9 percent plus 30 cents for each invoice paid online through its service. For some businesses, this invoicing solution is just too simple. For example, it doesn’t consider the needs of more complicated services-based businesses or those that mix products and services. It also can't create estimates or quotes, a deal breaker for some types of businesses like those involved in catering.
  • Very simple to use
  • Works with many third-party products and services
  • No estimates
  • No multi-currency support
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