Many CFOs don’t know their true revenue leakage rate. When asked, the answers range from:
Yes
No
Scared to check
Why the blind spot? Because billing often runs in the background, spread across multiple systems. It’s not a “hero process,” like sales, but it’s key to customer experience, audit readiness, and business scalability. Most of all, billing is fundamental to
trust. When it breaks, relationships break – internally with sales, product, and finance, and externally with customers and investors.
The reality is that many companies are held back by billing systems that function poorly. And unfortunately there’s a lot of inertia around fixing them. 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. And even if funding is available, for many the fear of disruption
outweighs the frustration of inefficiency.
Doing nothing over a long period leads to compounding problems. You need to grit your teeth and take action. Here are 5 steps to take to start moving towards control and away from chaos:
Step 1: Run an audit to surface leakage
At a recent dinner in New York,15 CFOs were asked to raise their hands if they thought their company had revenue leakage. Every hand went up.
What to do:
– Run an audit on a decent sample of invoices so you can estimate overall leakage.
– As part of that audit, identify the causes of discrepancies. They’re likely to include: using outdated pricing; not tracking usage; and not being able to calculate bills reliably (ie it’s beyond someone’s spreadsheet skills). Once you know the reasons,
you can start taking action.
– Watch out for customers on the wrong plans; a lack of automation in business processes means you can often find customers on endless free trials.
Step 2: Redefine billing as a trust system, not a back-office task
Confusing invoices are a customer churn risk. Sloppy billing data is an investor red flag.
What to do:
– Emphasise to your teams that billing is a core control system
– Align Finance, Sales, and Customer Success on how usage → spend is tracked and communicated
– Ask: Could we defend every invoice in an audit tomorrow?
Step 3: Think backwards from the customer experience
If you’re pricing based on usage, pricing becomes part of the product – customers need to know how much they’re using, and what implication that has for the bill they’ll receive at the end of the month. And today’s customers increasingly expect this information
to be available in real-time. They can check their phone usage or bank balances instantly- why should your SaaS bill be any different?
What to do:
– Provide customers (and your CS team) with daily mid-billing cycle running totals (and ideally even more frequently)
– Add detail to invoices so the “bottom line” is easily understood.
– Test transparency: Could a customer predict their invoice before receiving it?
If you can’t clearly explain your billing, you won’t survive an audit, fundraising round, or exit.
Step 4: Modernise without an overhaul
The mere thought of a transformation project raises concerns about endless IT interventions. 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. ERP overhauls take years and drain budgets. Middle-office add-ons add complexity
instead of solving it.
What to do:
– Don’t rip and replace. Instead, augment and enhance. You need to focus on what’s missing, so that your existing CRM, CPQ, and ERP can ‘just work.’
– This includes a dedicated usage-metering and rating layer to handle complexity without bloating your core stack
– And an integration layer to automate data flows across systems
The goal isn’t a new system, it’s a stronger monetisation backbone.
Step 5: Fix that hidden layer, and you go from chaos to control
When billing is fragile, multiple functions get blocked. Finance struggles with invoicing and audits. Product can’t ship new features and packages fast enough. Sales and Marketing can’t introduce new pricing fast enough.
But when billing is automated, accurate, and transparent:
– Month-end close shrinks from weeks to hours
– Pricing innovation doesn’t wait on IT
– CFOs and FP&A teams gain real-time data for strategic decisions
Billing doesn’t need a full system overhaul – it needs visibility, automation, and trust. Left unchecked, chaos takes over with teams scrambling to close the books, revenue slipping through the cracks, and customers growing frustrated. But with an intelligent
approach, control is achievable: faster closes, scalable pricing, stronger revenue integrity, and no more sleepless nights.
