Imagine preparing for a big race after months of intense training, only to find that your shoes have worn through, key pieces of your gear are missing, and your stopwatch is giving inconsistent readings. Despite all your preparation, keeping pace will be difficult.

This is what it can feel like for a business struggling with a broken billing process. And it’s the CFO’s responsibility to fix it. But how can they address a problem that impacts not only finance, but also customers, sales, and product?

Trying to run at full speed without the right tools means billing teams scramble to close the books, errors creep in, revenue leakage goes undetected, and audits become painful. Customers, meanwhile, are left confused by invoices they don’t understand. Sales teams are frustrated because billing can’t keep up with the deals they design, while product teams are hampered when billing fails to support new features and packaging.

If billing isn’t right, everyone suffers. Internally, this inefficiency creates stress, waste, and blind spots. Externally, it erodes customer trust. What starts as an inconvenience eventually becomes an urgent problem that demands attention.

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Many organisations, particularly in the SaaS industry, struggle to align complex billing processes with rapidly evolving business models, especially the shift toward usage-based pricing. As they try to adapt, companies often assume they need a major overhaul of their monetisation stack, including implementing a new middle-office system or billing platform.

But it doesn’t have to be that way. Solutions that work seamlessly alongside existing CRM, CPQ, and ERP systems offer a cost-effective, low-risk path to modernisation. Rather than replacing core systems, they act as an invisible enabler, providing the data infrastructure to handle complex usage metering and rating, along with an integration layer that automates data flows across systems.

This approach minimises implementation risk, and transforms billing and pricing operations from a mundane back-office function into a strategic capability. When the monetisation stack is more automated, less fragile, and more agile, that is a great platform for growth and scalable monetisation.

The myth of the overhaul

The stakes are high. According to a survey by Grant Thornton, CFOs continue to struggle with the costs associated with overhauling their finance systems, which remains a major barrier to improving operational efficiency. More than half of finance leaders in their latest survey identified digital transformation as a top challenge, with 64% citing IT upgrades as a priority area for the coming year. Yet, the costs of these projects, particularly the upfront investment and operational strain, often force companies to delay or scale back their plans.

This creates a significant dilemma. Despite advances in clever tech, many companies still believe they need to overhaul their entire ERP or add cumbersome middle-office solutions, projects that can take many months (or even years), drain budgets, and often fail.

Speak with CFOs, it becomes clear why tackling billing operations is so daunting. Teams rely on the tools they are accustomed to, with workflows and processes deeply embedded in existing systems. The mere thought of a transformation project raises concerns about endless IT interventions, disruption, soaring costs, and the risk of failure.

According to research from StrategicCFO360, 61% of CFOs report that lengthy implementation processes and the manual effort required during system transitions lead to substantial operational inefficiencies and revenue delays.

The answer can’t be to do nothing, because that’s like ignoring a blister caused by your running shoe. It hurts like hell in the short term, and eventually, it’ll force you to stop.

The risk of inaction in billing operations 

#1 Revenue loss from inefficient billing

The challenges compound each month a company operates with inefficient billing. At a recent dinner with 15 CFOs in New York, SaaSonomics Managing Director Todd Gardner asked everyone to raise their hands if they thought their company had revenue leakage. Every hand went up.

This is typical in SaaS companies with usage-based elements in their pricing, and is caused by a lack of automation. For example, a SaaS company I’m familiar with discovered a major oversight in its billing model: they offered a free tier allowing customers to use the product within a usage threshold or for a limited time, typically three months, before requiring payment. However, many accounts continued using the service for free, indefinitely.

Without proper governance or billing structures in place, the company was unknowingly giving away its product, leading to significant revenue loss. For CFOs, this kind of oversight is a ticking time bomb—an invisible, ongoing financial drain that they must address.

#2 Transparency around bill calculations

CFOs are facing increasing pressure to adapt to changing customer expectations around transparency. Businesses and consumers alike have grown accustomed to real-time access to financial data; for example, being able to check their phone usage or bank balances instantly through mobile apps.

This shift is putting pressure on billing systems.  Companies don’t just need to be able to calculate the right bottom line number when invoicing.  They need to provide enough information on that invoice so that the customer understands how that bottom line number is calculated.  And they need to provide on-demand mid-month ‘running totals’ – via customer-facing roles such as Sales and Customer Success, or directly to the customer as part of the product – so that customers can understand (and control) how their usage translates to spending.

There’s a canary in the coal mine here.  If a company cannot clearly explain its billing to customers, then it will struggle to respond confidently to probing around revenues in audits or due diligence. In short, it points to a compliance and controls risk which could jeopardise audits, fundraising, and exits.

How are smart companies fixing billing?

As pressure mounts to address these challenges, forward-thinking CFOs focus on optimising their existing systems rather than replacing them. This involves pinpointing key gaps, such as data infrastructure to handle complex usage metering and rating requirements, and an integration layer to automate data flows between systems. An invisible integration layer will transform a clunky and calcified monetisation stack.  Here’s how this approach can help:

• Automated connections between systems: An invisible integration layer connects systems like Salesforce and your ERP, making it possible to modernise billing without disrupting current processes and workflows.
• Real-Time Access: Teams and customers can view up-to-date usage and billing data.
• Accuracy: Automated billing plus fully-featured usage data processing capabilities help businesses avoid revenue leakage and ensure that invoices are accurate and timely.
• Faster Processing: Invoicing and month-end close can be reduced from weeks to hours.
• Flexible Pricing: New pricing models can be implemented without waiting for IT to write and test complex code.
• Strategic Insights: With real-time visibility into billing and usage data, CFOs and FP&A teams can make more informed decisions, improve profitability, and drive business growth.

A huge benefit of this approach is the ease of implementation. By focusing on filling the gaps between existing systems rather than replacing them or introducing a major new middle-office solution, the transition is smoother.

It’s also less risky.  This includes being able to run parallel billing processes during the transition (typically for two to three billing cycles) to test the new platform fully before cutting over.  Incidently, this parallel process almost always throws up surprising discrepancies in calculated amounts that shine a light on unexpected revenue leakage – at the point you fix the problem, you realise it was bigger than you thought.

This shift presents an opportunity

Usage-based pricing (UBP) continues to gain traction, often in combination with) subscription models. In 2020, only 30% of software vendors used UBP; today, it’s over 80%. This shift, driven by innovations such as the introduction of AI features and the rise of API-driven businesses, unlocks new revenue streams.  It can create huge challenges for CFOs when their monetisation stacks are not designed to handle these complex pricing models.

But there’s opportunity here as well as threat. By rethinking how the overall monetisation stack works, finance teams can become proactive partners in business transformation, enabling both strategic initiatives and financial health.As a result, what used to take days now takes hours. What was once error-prone is now error-free. Finance teams are no longer bottlenecks, blocking new pricing, delaying invoices, or dealing with constant firefighting. Instead, they’re enablers, driving growth and efficiency.  Revenue leakage disappears.

And the surprising thing is that this modernisation can happen without a full system overhaul. No more obstacles, no more scrambling to catch up.

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