Stripe is brilliant at what it was built for. It makes it easy to launch a SaaS product, charge a credit card, manage subscriptions, and handle tax calculations across jurisdictions. For early stage and mid market self serve models, it works seamlessly.
The challenge appears when SaaS companies move up market.
Enterprise customers do not behave like self-serve users. They ask for invoices instead of card charges. They request 30, 45, or even 60 day payment terms. They negotiate custom pricing, multi year contracts, and complex billing arrangements. Suddenly, the simplicity of automated card billing gives way to something far more operationally demanding.
This is the point where many SaaS finance teams realise that Stripe alone is not enough.
Enterprise Deals Shift Payment Behaviour
In self-serve SaaS, revenue and cash often move together. The customer enters their card details and payment is captured instantly. Failed payments trigger automated retries. DSO is low or almost irrelevant.
Enterprise SaaS changes that dynamic. Payment typically follows this path:
• Contract signed
• Invoice issued
• Invoice routed through accounts payable
• Internal approval processes
• Payment scheduled on batch cycles
Even with 30 day terms, actual payment might arrive on day 45. Some enterprises pay strictly on their internal cycle regardless of your terms.
This introduces true receivables management into a business that previously relied on automatic capture.
Custom Contracts Create Billing Complexity
Enterprise SaaS contracts are rarely simple monthly subscriptions.
Common scenarios include:
• Tiered pricing based on user volumes
• Hybrid models combining fixed fees and usage
• Milestone based implementation fees
• Multi entity billing under one master agreement
• Annual upfront fees with mid term expansions
These structures require careful invoice accuracy. A small discrepancy in usage calculation or discount application can trigger disputes that delay payment by weeks.
Stripe handles subscriptions well, but enterprise billing often involves manual intervention, approvals, and reconciliation across systems.
PO Requirements and Vendor Onboarding Delays
Large enterprises frequently require:
• Purchase order numbers on invoices
• Vendor onboarding approvals
• Tax documentation validation
• Specific invoice formatting
If an invoice is missing a required reference, it may be rejected automatically. The AR team only discovers the issue weeks later.
This is not a payment refusal. It is administrative friction. Yet it extends DSO significantly.
Enterprise SaaS companies must align billing workflows with customer procurement requirements, not just internal subscription logic.
Payment Terms Drift and Concentration Risk
As SaaS companies scale into enterprise, customer concentration increases. A handful of large clients may represent a significant portion of ARR.
If those customers operate on 60 day terms, cash flow risk intensifies.
Monitor:
• Exposure per enterprise account
• Payment behaviour versus agreed terms
• Percentage of receivables tied to top five customers
Stripe will continue processing card payments for smaller clients, but large enterprise invoices require structured follow up and exposure monitoring.
Some SaaS companies introduce account receivable automation software at this stage to manage invoice tracking, reminder cadence, and customer level visibility. The goal is not to replace billing systems, but to add discipline to collections as enterprise exposure grows.
Dispute Management Becomes Formal
Enterprise customers often raise detailed queries. These might relate to:
• Usage calculations
• Contractual discount interpretations
• Service credits
• Implementation scope
Unlike small customers, enterprise accounts typically involve multiple stakeholders. Resolving disputes can require coordination between finance, customer success, and legal.
If disputes are not logged and tracked carefully, reminders may continue inappropriately or payments may stall without clear accountability.
Enterprise AR requires structured dispute workflows, not informal email exchanges.
Multi Currency and Tax Complexity
Global SaaS companies invoicing enterprises must navigate:
• Multi currency billing
• Local tax regulations
• VAT or GST compliance
• Exchange rate exposure
An invoice error in tax calculation can delay payment while corrections are processed.
Stripe supports international payments, but enterprise invoicing often involves ERP integration and manual oversight to ensure compliance accuracy.
Forecasting Cash Becomes Less Predictable
In subscription SaaS, revenue predictability is often equated with cash predictability. Enterprise invoicing breaks that link.
Cash flow forecasting must consider:
• Payment cycle variability
• Procurement approval timelines
• Dispute resolution delays
• Seasonal enterprise payment behaviour
Finance teams must build models that account for behavioural lag, not just contractual terms.
This is where receivables management becomes a strategic function rather than a back office task.
Aligning Sales, Customer Success, and Finance
Enterprise SaaS growth is typically sales driven. Sales teams may negotiate extended terms or flexible billing to close deals.
Without cross functional alignment, exposure can escalate quickly.
Establish:
• Clear approval thresholds for extended terms
• Shared visibility of overdue enterprise accounts
• Escalation processes agreed across teams
When everyone understands the cash implications of enterprise contracts, discipline improves.
Conclusion
Stripe remains a powerful foundation for SaaS billing. But as companies move into enterprise markets, invoicing becomes more complex, payment cycles lengthen, and exposure concentrates.
At this stage, managing receivables requires deliberate structure. Whether through refined internal processes or the addition of account receivable automation software, the focus must shift from transaction processing to exposure control.
Enterprise growth is valuable. But without disciplined invoicing and follow up, ARR expansion can mask underlying cash flow strain. When Stripe is not enough, the solution is not abandoning it. It is building the receivables infrastructure that enterprise scale demands.
