9-Point Checklist to Choose the Right Billing System for Your Business

From stakeholder needs to integration requirements and global standards, equip your business for success with a billing solution tailored to your unique requirements. We help you assess your billing needs and share a list of 9 considerations for selecting an efficient billing system.
December 20, 2023
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Choosing a new billing system is no mean feat. 

They are an indispensable part of the quote-to-cash process. From generating a quote and issuing timely invoices to sending payment reminders, collecting payments, and tracking revenue — billing systems constantly keep some of the most critical aspects of your business under check. 

A good 37% of finance leaders believe that ‘prompt invoicing’ could greatly help in enhancing cash flow. Billing is a mission-critical function that will help you avoid late payments and significantly improve cash flow.

On the contrary, billing systems that are rigid, slow, error-prone, or grappling to cope with the agility required for modern-day dynamic pricing are only going to hold back your business from scaling up and unlocking new revenue opportunities.


There are a host of factors that you need to take into account when you’re on the lookout for a billing system, so we want to make this easy for you. We’ve put together a list of the key things to consider when you’re choosing a new billing system. But first, let’s understand your billing needs and customer preferences better.

What are your billing needs?

Before you set out to hunt for a billing tool, it’s important to assess your billing workflows and internal processes to understand the capabilities that you need to be looking out for.

Here are a few questions to analyze your needs:

  • Who is going to be using the billing system within your organization?

Think of all the stakeholders involved, right from the point of creating contracts and sending out invoices to handling usage data to following up with customers for delayed payments to creating accounting entries.

  • How technically well-versed are they?

This will help you understand how automated the billing system needs to be and how easy and intuitive the self-serve functionalities of this system need to be.

  • If you have a usage-based pricing model, how are you currently managing metering and usage data?

You will need a billing tool that is compatible with your business's usage-based pricing model and flexible enough to integrate such usage or consumption data into your billing system.

  • Do you provide prepaid or postpaid billing, or a combination of both?

Based on this, you can decide the automation capabilities of your billing tool and the kind of dunning functionalities that you will need in your billing tool.

  • What are your dependencies on your billing tool for your accounting workflows?

You need a billing tool that aligns well with accounting processes and adheres to regulatory compliance standards, especially for the more involved revenue recognition rules like ASC 606 and IFRS 15. 

What do your customers need?

Let’s face it, billing systems at their worst could risk customer frustration and potential disengagement, lost revenue, and poor capital efficiency — impacting long-term business success.

Source: Tweet 1 and Tweet 2

According to a report by Deloitte, when it comes to billing model preferences — a majority of clients would like to have some form of spending commitment. 

Let’s take a look at some of the interesting report findings:

  • More than 90% of clients stated that they disliked receiving an invoice at the end of the month based on their actual usage. Clients hate “bill shocks,” and for many of them, making software spending predictable was a top decision driver.
  • In the B2B software world, close alignment between payment timing and product adoption was another key requirement for most clients.

Additionally, beyond receiving invoices in their inbox, customers also value features that allow them to track usage data or receive alerts related to provisioning, like notifications when their credit balance is running low.

Businesses need to opt for a billing system that not only addresses these customer requirements but also aligns with their industry, business goals, accounting rules, and cash flow philosophy. 

A checklist for choosing your billing system

To help you supercharge your billing workflows, we’re sharing the top 9 things that you need to keep in mind when you set out to choose a billing system.

Let’s break this down for you.

1. Stakeholders and their needs

Typically, most organizations have the following stakeholders involved in the quote-to-cash process:

  • Sales
  • Finance/account manager/customer success
  • Collections
  • Accounting
  • Business management
  • Product and tech

It’s important to ensure that the billing system you select is solving the pain points that stakeholders in your organization are dealing with. 

Sales teams

Consider how sales teams contribute to the overall billing process, from contact management to potential points of engagement throughout the billing lifecycle. Most sales teams initiate the billing process by getting contacts into the system. Ensure that the billing system that you opt for also effortlessly syncs with the tools used by sales teams to create contracts and automatically retrieves contract data from those sources. The billing system’s interface needs to be simple and intuitive, with clear navigation and control options. It should provide a hassle-free billing experience for sales teams.

Finance/account manager/customer success teams

For the finance teams, account managers, and customer success executives, browsing through invoices and cross-checking them to ensure they are correct should be made easy. All the data from different internal systems needs to be pulled in correctly to the billing tool, empowering finance teams to effortlessly identify and resolve billing issues.

Collections teams

Collections become a hassle for your teams, primarily when dealing with a sizable customer base or opting for non-auto charging mechanisms. Implementing a robust receivables system is crucial to prevent overdue accounts, streamline debt recovery processes, and enhance cash flow through automated payment reminders. Select a billing system that has a seamless process in place for sending out timely payment reminders, creating a proactive approach to streamline collections and minimize involuntary churn.

Accounting teams

Choose a billing system that supports advanced accounting needs. Each company uses accounting rules that are sometimes quite complex and differ in nuanced and subtle ways. The billing tool should automate the process of passing accounting entries, regardless of the complexity involved. Opt for a billing system equipped with a flexible and easy-to-configure accounting rule engine to meet your specific requirements. A billing tool that automatically generates accounting entries based on billing workflows eliminates the need for accounting teams to manually download data from various systems in the required formats. Additionally, a billing tool with the capability to automatically recognize revenue in accordance with regulations like ASC 606 and IFRS 15 would be highly beneficial for accounting teams in terms of financial reporting.

Business management teams

For effective business management, a billing tool should extend beyond basic tracking to equip teams with real-time or, at most, daily analytics on diverse metrics. This includes analytics derived from contract and revenue data such as Monthly Recurring Revenue (MRR), Annual Recurring Revenue (ARR), and churn metrics, along with data on user base growth, usage patterns, and trends. These insights will empower teams to identify growth opportunities, make strategic decisions, and manage financial performance with ease.

Product and tech teams

For companies with sizable customer bases, involving product and tech teams in the billing process is common. Billing tools should enable product and tech teams to easily automate interacting with contacts and sending usage data. In provisioning and entitlement cases, the billing system should accurately track and facilitate easy access to relevant data, including analytics on top of it. The billing tool should offer robust API integrations, allowing automated data exchange across diverse business systems and applications. Ideally, billing tools should provide APIs that are essential for customer and contract management, usage data transmission, entitlements, provisioning, and retrieving outputs such as invoices, monitoring data, and analytics. This functionality will not only automate internal workflows but also equip customers with timely reports and insights.

2. Integration requirements

Prioritize smooth connectivity, where every aspect of your billing system effortlessly integrates with the rest of your tech infrastructure. Look for capabilities that enable smooth integration with essential components, such as:

  • Payments
  • ERP
  • Sales tax
  • Metering/usage data
  • Provisioning 

Integration with the tool of your choice is key, given how you have multiple internal dependencies and existing processes are built around those tools. 


Sales teams utilize Customer Relationship Management (CRM) and Configure, Price, and Quote (CPQ) tools for a range of tasks that include managing their deal pipeline and creating quotes. In some companies, this data is manually entered into the billing tool due to the lack of integration between these tools. This leads to duplicate data entry, systems that are out of sync, and errors due to human intervention. To streamline this process, it's crucial to choose a billing tool that integrates with CRM and CPQ tools, ensuring accurate data retrieval and automating invoice generation, even for complex contracts.


In the era of expanding digital payment choices, it is essential to provide customers with flexible payment options. Your billing system should smoothly integrate with various payment gateways to offer the variety of payment methods that exist today, ensuring a smooth transaction experience. Additionally, the billing tool should be capable of automating alerts for payment receipts, pending payments, failed payments, and expiring credit cards. Proactivity in communication enhances customer engagement and helps reduce the risk of customer turnover.


Accurate financial reporting depends on seamless integration between billing tools and the Enterprise Resource Planning (ERP) system. Choose a billing tool that effortlessly syncs with your ERP, eliminating manual back-and-forth data handling. This saves a lot of manual effort from your accountants as well as back and forth with various teams to get the right data from your billing system into your ERP and eventually close your books on time. All the information needed to create journal entries related to your customers is present in your billing system. A seamless integration ensures this data flows into your ERP without manual intervention. 

Sales tax

The integration of the billing system with specialized sales tax tools becomes a necessity, as it streamlines the complex task of sales tax calculation. A seamless integration reduces the potential for errors and ensures compliance with dynamic tax regulations and the accurate reporting of sales tax across various jurisdictions. 

Metering/usage data

One way to reduce engineering bandwidth is to opt for a billing tool that integrates smoothly with multiple data sources that hold your metering data. This is because different methods of integration are useful in different situations. Quick uploads of CSV files are great for quickly getting started with a billing system. The manual entry of usage data using a web interface is useful for products where the usage is quite low and tracked manually. The billing system's ability to plug into different sources of data (such as your product database or your company’s data warehouse) helps you integrate your original source of data directly with billing without any effort from your engineering team. The billing system having APIs to send usage data is useful for an integration that is easier to maintain in the long run but demands more upfront engineering effort.


Select a billing tool that seamlessly integrates with the provisioning process. This integration will ensure an accurate reflection of customer purchases from contracts in the billing system into your product systems. As services or products are provisioned or modified, the billing system should be able to send real-time updates, keeping your product’s provisioning system in sync with the contracts that your customers sign. 

3. Different billing models

You don’t want to be playing catch-up with the ever-evolving complexities in billing logic and pricing models. Your billing tool should be able to offer your teams the flexibility to experiment and switch between different pricing models as your product iterates and evolves over time. Select a billing tool that not only comes with capabilities to cater to your current needs and existing pricing models but is also able to automate pricing model experiments in the future. This allows you to explore different business models and usage meters to maximize revenue.

  • Opt for a billing solution that has the capability to accommodate various pricing models. Be it one-time charges, recurring subscriptions, postpaid based on usage, prepaid with postpaid overages, prepaid with provisioning (requiring top-ups for credit depletion), or any combination thereof — choose a tool that effortlessly handles the complexity of your billing models. This is really important so that you never have to think about switching billing systems in the future as your pricing structures evolve.
  • Billing systems that are not future-proof are in many ways rigid, slowing down your sales teams, limiting their ability to get creative with contracts, and eventually affecting your revenue goals. The billing system should empower sales teams with limitless pricing flexibility and contract configuration capabilities, fostering agility in strategy execution. 

4. Comprehensive reporting capabilities

The billing system should equip you with powerful reporting capabilities. This will help you gain actionable insights around churn rate, active subscriptions, usage aggregates, customer balances, revenue numbers, etc., ideally along with customer segmentation insights, empowering informed decisions. Moreover, Deloitte’s report further reveals that customers have also shown interest in receiving insights pertaining to their current and forecast usage as well as spending.

  • The billing system you opt for should provide in-depth financial reports and tax summaries, offering a comprehensive overview of your business's fiscal health.
  • Real-time reports of incoming cash and related revenue numbers will help you stay on top of your cash flow and plan ahead with ease. 

5. Self-serve functionalities

Billing systems with self-serve options are incredibly helpful in gaining better control over billing processes, streamlining operations, and reducing dependency on your internal teams. Evaluate how a billing tool saves you the costs associated with hiring a team to manage the billing and invoicing workflows.

  • Self-serve functionalities that don't demand engineering intervention will help finance teams navigate billing complexities with ease, leading to increased productivity and minimizing operational challenges.
  • These capabilities will also give financial operations teams and other stakeholders more time to enhance product features, meet service delivery benchmarks, and identify new customer service strategies.

6. Robust security measures

Minimizing the risk of data breaches should be a top priority for every business. Select a billing tool that is backed by robust security measures that are designed to safeguard your billing operations and customer data.

  • Choose a tool that implements two-factor authentication, adding an extra layer of security to your billing processes. Implementing two-factor authentication for critical billing systems not only secures your organization's data but is also imperative for meeting your security compliance requirements.
  • Ensure the billing system enforces stringent access controls, safeguards confidential customer data, and creates a secure billing environment for your business.

7. Efficient compliance management

Owing to the ever-changing compliance and regulatory environment, the billing system that you select should help you address the evolving dynamics of global regulations and the required standards for your industry.

  • Consider the billing system's capability to handle the diverse landscape of tax regulations in global markets.
  • Ensure the billing system excels in handling regulatory requirements like ASC 606 and IFRS 15 on revenue recognition and meets payment card industry standards.

8. Reliable customer support

If you ever run into a hitch managing your billing processes, quick and reliable customer support from the billing system will help you resolve issues with ease.

For a crucial system like your billing tool, having prompt and reliable support from the billing vendor is essential, particularly given that the quote-to-cash process engages various stakeholders within your organization and issues that arise are typically of higher criticality than usual. Without this support, internal team members tend to take on the role of customer support, aiding other stakeholders in overcoming obstacles they encounter in the process.

  • Right from the point of simplifying implementation and the onboarding processes, billing systems should provide documentation, quick guides, and developer tips to facilitate a quick and efficient adoption.
  • Responsive and dependable customer support via chat, calls, or emails is essential for receiving timely guidance and solutions, preventing disruptions, and ensuring streamlined billing workflows.

9. Global billing standards 

As you step into new markets, billing systems designed for international success will be crucial to embracing global business standards with ease.

  • Firstly, it should provide multi-currency capability. For example, a software company expanding into Europe might price its products in euros for customers in Germany while offering them in pounds for customers in the UK. This not only attracts a global customer base but also supports competitive pricing strategies in international markets and minimizes currency exchange complexities.
  • Along with ensuring accurate time zone logic, the billing system needs to use the correct decimal and thousand separators to ensure the customers are billed correctly — for the right amount, at the right time.
  • Furthermore, ensuring global tax compliance is essential. The billing system should be equipped with integration capabilities, particularly with sales tax providers like Avalara. This integration empowers the system to adapt to various tax regulations across different regions, automatically applying the correct tax rates and handling tax calculations, such as VAT in Europe or GST in Australia, to ensure compliance and prevent legal issues.

Bottom line

The key to success lies in finding a billing system that not only meets today's needs but also proactively prepares for tomorrow's challenges. Zenskar is a perfect fit, offering more than just a solution for your current billing demands. 

With Zenskar, you can future-proof your operations by leveraging a robust, secure, user-friendly, and scalable platform that adapts seamlessly to the ever-evolving billing and pricing dynamics. Say goodbye to coding complexities and effortlessly automate contracts and pricing models with Zenskar’s best-in-class solutions!

Don't miss out on transforming your billing experience — book your demo today and unlock the power of streamlined billing processes.

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