How to choose the right automated invoice generator for your business

Best automated invoice generator options

Automated invoice generation reduces errors, ensures timely billing and frees up time for you to focus on activities for growing revenue.

The challenge is knowing which invoicing system to use. With so many options, how do you know which software is right for your business?

By the end of this article, you’ll discover what an automated invoice generator does, three top options on the market, the benefits of using automatic invoicing software and what features to look for when choosing one.


What is an automated invoice generator?

Automated invoice generators simplify billing by creating, sending and tracking invoices. An automatic system creates invoices based on the data you provide, such as:

Business and customer information

  • Your company name

  • Customer contact details (including the client’s name, email address and phone number)

Payment details

  • The total amount due

  • The invoice number

  • The invoice date

  • The purchase order number (if applicable)

  • Payment due dates

  • Payment terms (like credit sales with 30-day, 60-day or 90-day schedules)

  • Discounts or promotional offers

  • Payment method (like your bank account details or links to online payment solutions)

  • Tax details (like VAT, if applicable)

Overview of products and services

  • An itemized list of the products or services sold (known as line items)


The software pulls this information into an invoice and sends it to the right customer at the right time. It also automates payment reminders and tracks payment statuses, allowing you to see:

  • Which customers receive invoices

  • When customer payments are due

  • Which invoices are overdue

The entire process ensures timely billing and streamlines your invoicing operation. You spend less time creating invoices and chasing payments and more time generating leads and closing deals.

Note: The exact features of an automatic invoice generator vary. Most will automatically create invoice amounts, track payment statuses and automate reminders, while some might not. Review your chosen system’s complete list of features to clarify what it offers.


What to look for in automatic invoicing software

With many invoicing platforms available, how do you know which system is right for your business?

Here are some must-have features to help you make your decision.

Note: The features you need depend on different factors, such as your industry, the size of your company and your specific business needs. Using this list as your starting point, consider what elements will help you create the most efficient invoicing operation.


Integrations

Integrations ensure that an invoice generator works well with your existing systems. They let you transfer data seamlessly between different platforms, making your processes more efficient.

Say that you connect an invoice generator with a CRM like Pipedrive. Customer details transfer into the invoicing system, enabling quick and accurate invoice creation. You spend less time adding customer data to invoices, meaning you can focus on more important activities like nurturing leads.

Key integrations to look for:

  • CRM systems. Integrate with your CRM to create a seamless flow of customer data. Pull client details (such as contact information and payment terms) into invoices and track all client interactions in a single location.

  • Payment gateways. Connect payment gateways (such as Stripe) to streamline the payment process. Share the secure payment links to give customers a fast and efficient way to pay.

  • Accounting software. Combine your invoicing system with your accounting software (such as QuickBooks or Xero) to centralize your financial management. Keep track of payments in a central location and reconcile transactions with just one click.

Usability

A simple interface helps sales reps easily create invoicing automation, ensuring a smooth and efficient invoicing process.

Imagine a sales team trying to create personalized payment reminders for different customer segments. The invoicing system is hard to navigate, with a clunky interface and no way for reps to find out how to set these reminders.

A user-friendly interface removes these hurdles. The system is easy to navigate, with a simple interface and search functionality. As a result, sales reps can quickly figure out how to create personalized reminders for different segments.

Key usability features to look for:

  • Search and filter options. Search functionality helps users find specific features, invoices or payment records. Your team can locate the necessary information if something isn’t immediately visible or available.

  • Intuitive dashboards. Look for a system that displays essential information – like outstanding invoices or upcoming payments – in a unified dashboard. Ensure you can customize the dashboard to view crucial financial data, including upcoming or overdue payments.

  • Error notifications. These create alerts for incomplete or incorrect fields before sending an invoice. Such safeguards minimize mistakes and ensure accurate communication with customers.

Customizations

Customizable features allow you to send invoices that align with payment terms. You can build an accurate invoicing process that reaches customers with the correct invoices at the right time.

Imagine that your business offers “Buy Now, Pay Later” plans for customers. With a customizable system, you can generate invoices that incorporate these payment terms. A customer on a 90-day payment plan receives invoices at regular intervals (after 30, 60 and 90 days).

Customers have a better buying experience when they receive accurate and timely invoices. The process is smoother for you because the system automatically sends invoices that align with your payment terms.

Key customizations to look for:

  • Customizable invoice templates. Look for systems that offer template customizations, like uploading your branding or adding new invoice fields (for things like taxes or itemized product lists).

  • Flexible payment terms. Use software that enables specific due dates, payment schedules or recurring billing cycles for different customers.

Real-time insights

Live financial data allows you to track payment statuses in real time. You can immediately see paid, overdue and pending invoices, allowing you to make quick decisions to secure payment.

Suppose a sales rep uses a dashboard to monitor outstanding invoices. The rep sees an overdue customer payment despite the system sending them an automated reminder.

The rep follows up personally to speed up the process. They encourage the buyer to settle payment promptly while maintaining a strong customer relationship.

Key real-time insights to look for:

  • Live dashboards. Get an instant overview of payment statuses, track settled, overdue and pending invoices and make informed decisions to improve your cash flow.

  • Real-time reporting. Find a system that provides live reports to identify patterns. Use these reporting insights to improve your invoicing process and secure payments on time. For example, if you notice recurring late payments from the same client, you can reach out directly or adjust their payment terms.

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3 top automated invoicing software options

The ideal automated invoicing system should feature three key components:

  • Customizable features

  • A variety of invoicing automation

  • A user-friendly interface

Based on the above criteria, here are the three most effective and user-friendly systems to refine your software search.

1. Best for streamlining customer payments: QuickBooks

QuickBooks is an accounting system with financial capabilities like payroll and inventory tracking.

The software facilitates invoicing by integrating with popular payment gateways like PayPal and Apple Pay. Invoices all have a link to one of these payment gateways, which customers can click to settle payment instantly.

Here are some of QuickBooks’ other automated invoicing features:

  • Generating recurring monthly invoices

  • Sending payment reminders

  • Receiving automatic notifications when customers open an invoice

QuickBooks lets you add your company branding to its customizable blank invoice template. Take a look at this example of a QuickBooks custom invoice:

Automated invoice generator QuickBooks


Because of its accounting capabilities, QuickBooks is suitable for:

  • A growing small business that wants an invoicing system to scale with it

  • Medium-sized companies that need a full range of accounting features

How to generate invoices with Pipedrive and QuickBooks

Pipedrive’s invoicing feature integrates with QuickBooks, so you can create, view and send invoices to the software directly from your CRM.

To connect your QuickBooks account, click “Tools and apps > Invoicing” and select “QuickBooks”. You’ll then go to Marketplace to grant the app access to your account.

Automated invoice generator Pipedrive QuickBooks integration


After validating access, configure your QuickBooks invoicing preferences. Here’s how this information appears in Pipedrive:

Automated invoice generator Pipedrive QuickBooks invoicing preferences


Click the “Save” button to confirm your preferences. Now, go to the detail view of any deal in your Pipedrive CRM to create your first invoice. Open the invoice tab and click “+ Invoice” to start

Automated invoice generator Pipedrive QuickBooks adding invoice


Fill out the details of your invoice, which you can see below:

 Automated invoice generator Pipedrive QuickBooks integration create invoice


After creating your invoice, all the information will appear in your QuickBooks account.

Head to the Pipedrive-QuickBooks integration support page for more information on this process.

Note: Pipedrive’s QuickBooks integration is accessible by the user who installs it. The user can then share updates and invoices with colleagues from within the CRM.


2. Best for customizable invoicing: Xero

Xero is cloud-based accounting and invoicing software that simplifies financial management. The system’s customizable features for the automated invoicing process let you adjust the appearance and information to create on-brand invoices that match your payment terms.

For example, with the advanced invoice template (the custom DOCX template), you can insert new fields, edit existing fields or remove fields altogether. You can also add static text that remains the same in each invoice, like your terms and conditions (if they’re the same for every customer).

The system’s invoicing automation also allows users to:

  • Schedule reminders and updates based on customer payment terms

  • Receive instant payment notifications

Here’s how to automate invoice reminders in Xero:

Automated invoice generator Xero invoice reminder


Xero’s easy-to-navigate interface is suitable for smaller or medium-sized businesses with less time to learn a new invoicing solution.

Note: Xero also automates bank reconciliations. The platform matches statement lines from your bank accounts to transactions in the system to ensure that your records are accurate.


How to generate automated invoices with Pipedrive and Xero

Integrate Xero with Pipedrive using Make, a tool for building and automating workflows. The integration allows you to create invoices based on your CRM data.

To connect Pipedrive with Xero, select the “Install now” button on the Xero integration page and follow the instructions to link your accounts. You may also need to sign up for a Make account if you haven’t done so already.

From here, determine which data to sync between Pipedrive and Xero. For example, you can sync contacts, deals and more. After this, you can activate the integration. Your Pipedrive and Xero data will automatically synchronize based on your preferences.

3. Wave: best for usability

Wave is a web-based accounting system for small businesses. It provides a free invoice generator with free templates for quick invoice creation.

The software also comes with invoicing automation capabilities, including:

  • Invoice creation and distribution

  • Overdue payment reminders

  • Recurring billing for repeat customers

Note: Some Wave automation features, like late payment reminders and scheduling recurring invoices, are available to users on its Pro Plan.


Here’s where you create and send an invoice in Wave:

Automated invoice generator Wave invoice creation


The software also enables automatic notifications for key invoicing activities. For example, you can receive updates when a customer views an invoice and when they pay it.

Wave is suitable for startups and small businesses that want a user-friendly system that doesn’t require extensive training.

5 benefits of automatic invoice generation

Invoice generators reduce manual intervention – saving time, improving accuracy and enhancing the buying experience.

Let’s look at some of these benefits (and others) in more detail.

1. Save time

Automatic invoice generation frees up time for you to focus on more critical work activities.

Imagine your business has an extensive list of repeat customers. You create invoices for these customers every month.

An invoice generator removes the hassle of manually creating invoices – a time-consuming and inefficient process. The system makes the invoices, sends them to the customer, tracks payment statuses and automates reminders (depending on the features of your specific software).

As a result, you can focus on critical revenue-generating activities – like following up with leads.

2. Get paid quicker

Automation sends prompt invoice reminders, encouraging customers to settle payments quickly. When customers pay sooner, you have a more substantial cash flow to reinvest into your business.

An invoice generator sends customers automatic reminders a few days after they’ve received the initial invoice. The notification typically results in many immediate payments, boosting your cash flow.

Imagine you’ve been looking for ways to improve lead management and increase customer retention. With a healthy cash flow, you can invest in an efficient CRM system to achieve these goals.

The funds from these invoice payments allow you to purchase new software for your business, driving long-term business success.

How to automate invoice reminders in Pipedrive

With Pipedrive’s date trigger automation, you can encourage customers to settle invoices quickly. To centralize all client-related activities, email reminders for upcoming due dates directly from the CRM.

Here’s how:


To create date trigger automation, click ... > Automations” on your Pipedrive dashboard. Select the date trigger type on the right-hand side of the screen.

Automated invoice generator Pipedrive date trigger automation


After clicking “Date trigger”, specify the following:

  • The item that will trigger the automation (including activity, deal, organization, person or custom item)

  • The date the automation will trigger

  • The hour and timezone of the automation

When selecting the date, you’ll see three options:

  1. Exact date: the automation triggers on a specific day

  2. Before date: the automation triggers a certain number of days before the payment due date

  3. After date: the automation triggers a certain number of days after the payment date (for an overdue reminder)

Here’s how these options appear in Pipedrive:

Automated invoice generator Pipedrive date trigger


Click ”Apply trigger” to save changes and kick off the date trigger.

Note: Date triggers are part of the Automations feature. Currently accessible by a closed group of Pipedrive users, this functionality will become available to more users later. Always check the “New in Automations” pop-up for the latest feature updates and innovations.

Automated invoice generator Pipedrive New in Automations


3. Level up your reputation

Sending on-brand and professional invoices builds customer trust and boosts loyalty. According to Deloitte, 88% of customers will buy again from a brand they trust.

Put yourself in the shoes of a customer. You see an ad for a company on social media and head to the website to make a purchase. The invoice you receive has the same logo, brand colors and design elements as the ad and company website.

Consistent branding implies that the company:

  • Operates legitimately. Matching design elements indicate that a business has invested in creating a cohesive identity, often associated with reputable operations.

  • Values its image. A consistent brand identity shows that a company cares about maintaining a strong image, which reflects positively on customer brand perception.

As a result, you feel more secure in your purchasing decision, which encourages you to buy again.

4. Master your cash flow

Many automatic invoicing tools display the payment status of invoices as they occur. Real-time visibility helps you make fast and informed decisions about your cash flow.

Let’s say your company is considering investing in a new sales CRM. With the automatic invoicing system, you can see that:

  • Most customers have paid their invoices

  • Your cash flow is healthy

Knowing this information, you decide to pay for a new system. You know you have enough funds to cover the cost, so you’re protecting your business from a tricky financial situation (overspending without enough cash to support you).

5. Invoice right every time

Invoicing systems automatically insert the correct details, minimizing human error. As a result, you can:

  • Enhance the customer experience. Accurate invoices reduce the need for corrections, making the payment process smoother and more efficient for the customer.

  • Increase timely payments. An accurate invoice allows customers to settle payments faster. There’s no discussion about payment terms or due dates, which speeds up the payment process.

  • Keep your accounts in line. Accurate invoicing ensures you charge the right amount for your products or services. You reduce discrepancies and prevent errors in tracking your cash flow.

Correct data is essential for invoice accuracy. Before automating invoice generation, ensure client details, payment terms and order information are accurate to avoid errors. Also, regularly review and update your data to maintain invoicing consistency over time.


Automated invoice generator FAQs


Final thoughts

Automating invoice generation improves the customer-buying experience, saves time and improves accuracy. The challenge is knowing which invoicing system is right for your business.

Based on the above top invoicing generators and must-have features, look for a system with a user-friendly interface, customizable features and efficient integrations with relevant systems – like Pipedrive’s CRM.

Sign up for a free 14-day trial to see how Pipedrive can elevate your sales and invoicing process.

Driving business growth

Driving business growth