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When Stripe Billing Starts Breaking
The second your billing logic gets more complex, Stripe requires more manual setup and ongoing maintenance.
Here’s exactly why:
Stripe doesn’t support ramped contracts
Let’s say you close your first enterprise deal. They don’t want your standard monthly plan. Instead, they ask for a ramped contract
“Start us on a 3-month pilot at $1000, then $1,500/month for the next 6 months, and $2,000/month after that.”
But here’s the problem: Stripe doesn’t support this kind of flexibility out of the box.
You’re stuck trying to make it work with one plan per customer. You’ll either, manually track the ramp schedule in your backend, or set up multiple plans, each triggered at the right time.
So what started as one enterprise deal quickly turns into custom billing logic and the more you grow the harder it gets to maintain.
No Support for Quotes, Renewals, or Negotiated Pricing
Enterprise sales don’t start with a checkout button.
For example, if you’re closing a deal with a mid-market company, they ask for 500 seats, 3 add-ons, and a 10% discount if they commit to an annual plan. And that’s standard.
But Stripe doesn’t let you create a quote.
There’s no native way to send terms, lock in pricing, or get approval. So you spin up a PDF, negotiate over email, and track everything manually in Notion. Once the deal closes, you create a Stripe subscription that only vaguely reflects what was promised.
Now imagine the same customer wants to:
Add more seats mid-cycle
Renew early next year with new terms
Or switch from monthly to annual billing
You’re back to square one, manually editing Stripe plans, invoices, and internal records.
At scale, this isn’t just tedious, it’s risky. Without a source of truth for quotes and negotiated terms, things fall through the cracks. Customers get misbilled and trust takes a hit. And your ops team becomes the bottleneck for every deal.
AI and agentic companies that move upmarket hit this wall early. Not because their pricing is broken, but because they rely on Stripe’s infrastructure and can't support how real-world deals are done.
Stripe doesn’t support committed usage and credits pooling
When you start with usage based pricing, it starts simple but it doesn’t stay that way for a long time. At first, you’re charging $0.01 per API call which is easy enough and Stripe is capable of handling that.
Then a new enterprise prospect asks if you can commit to 1M calls a month at a discounted rate? You want to say yes, but Stripe doesn’t support it natively.
Then after some time, a bigger team signs up and asks to pool usage across all their seats. But the issue is that Stripe tracks usage per subscription and across users so pooling is out of question too.
Usage-based billing is supposed to scale with your product. But Stripe’s basic metering can’t keep up with the pricing models AI and agentic companies actually need.
Stripe doesn’t track contract changes or revenue schedules
Let’s say any of your existing enterprise customers that signed up with one team has now invited other teams too like, marketing, ops, even finance.
They ask:
“Can we add everyone under one account?”
“Can we get a single invoice for all teams?”
“Can our credits be shared across users?”
With Stripe, the answer is basically “no.”
It treats each subscription as standalone. No parent-child hierarchy. No way to roll up multiple accounts under one billing profile. No shared usage or credits.
So you either:
Create workarounds in your backend,
Or manually track everything in spreadsheets.
And when the company asks for an org-wide usage summary, you have to export data from five different accounts.
Stripe’s flat structure wasn’t built for modern AI and agentic teams that grow fast and scale across departments. But your customers expect the basics, centralized billing, shared entitlements, and clean reporting out of the box.
No support for granular filtering within usage events
You might start with one price for all API calls. But as you scale, that changes.
You’ll need to:
Charge differently for newer or premium LLMs.
Set different prices for different regions or currencies
Track usage types separately, like input vs output tokens
Take ChatGPT in August 2025:
GPT-4o: $2.50 per 1M input tokens, $10.00 per 1M output tokens
GPT-4 Turbo: $10.00 per 1M input tokens, $30.00 per 1M output tokens
GPT-4: $30.00 per 1M input tokens, $60.00 per 1M output tokens
Pricing complexity grows further when you start supporting multiple regions, currencies, or product types.
To handle this, you need granular filtering within usage events, so you can apply different prices based on model, region, or other metadata. Unfortunately, Stripe doesn’t allow you to filter or segment data within a single usage event.
So when you need to charge differently for GPT‑4o vs GPT‑4 Turbo, or price input and output tokens separately, Stripe forces you to create separate usage schemas for each variant.
For AI and Agentic companies with dozens of models or multi-parameter billing rules, this becomes a scaling nightmare.
Stripe doesn’t support feature-level usage limits
Most AI and SaaS products don’t just sell access, they sell limits.
Take InVideo as an example, like:
10 credits
50 video minutes
30 seconds of generative output
Each plan gives a different mix of these. That’s how tools like InVideo price. But Stripe can’t define or enforce limits to a feature tied to a plan and limit the access.
Recurring or one-time credits
Let’s say you’re building an AI platform with a credit system:
1 video export = 5 credits
Pro users get 100 credits/month
They can top up if they run out
But as soon as you go beyond this basic setup, things get tricky. For example, if you want to:
Give recurring credits every month
Roll over unused credits
Auto top-up when credits fall below a threshold
Stripe doesn’t support any of that natively. It only handles one-time and promotional credits. For everything else, recurring logic, rollover rules, wallet monitoring you have to build and maintain your own credit system on top of Stripe.
The more your pricing evolves, the more infrastructure you write just to make Stripe work.
No support for custom credits
At first, credits feel simple. You give 100 sign-up credits, charge 10 credits for X, 20 for Y, done. But overtime you realize that not all features cost the same to run.
Let’s say:
Creating a table costs 50 credits but barely any compute
Enriching rows costs 10 credits but uses a large language model and consumes high GPU time.
You’re charging less, but compute costs are higher. Eventually, finance flags this and you understand that you’re losing money on certain actions. So you try pricing based on GPU seconds or usage tiers, but now customers don’t understand their bills.
So for you the obvious solution is to convert all actions and assign credits to it. But Stripe doesn’t support that. You can’t assign different credit values based on backend cost. You’ll have to build your credit engine just to keep margins intact.
Why Teams Choose Flexprice
Over Stripe?
1. Handle hybrid pricing automatically
Hybrid pricing, where a customer pays a base fee and then usage-based overages, works out of the box with Flexprice.
You can define a plan like: $99/month for 5,000 API calls, with $0.01 per extra call. Flexprice tracks both the base quota and overages automatically.
Your customer always sees how many calls they’ve used, what’s left in their plan, and what they’ll be charged beyond the limit, in real time.
If the plan changes, say the base quota increases or the overage rate changes, Flexprice updates everything across usage tracking, billing, and customer dashboards instantly. You don’t need to rebuild anything or touch the logic in five different places.
"We had to launch our new product and needed a billing solution that could handle billions of events without any latency issues or downtime. Flexprice ensured smooth operations and gave us the confidence to scale"
Divyanshu
Founder
2. Handle hybrid pricing automatically
With Flexprice, you don’t need to create a separate usage stream for every model, variant, or pricing rule.
You can send one unified event like api_call with properties such as model: gpt-4-turbo or tokens_out: 100. Flexprice applies the right pricing automatically based on those values.
This means you can charge differently for each model, count input and output tokens separately, or price based on other custom parameters all from a single event stream.
3. Integrated Feature Entitlements
Flexprice lets you define what a user gets with each plan like credits, video minutes, or access to premium features, all in one place. You can set usage limits for each of these, track them automatically, and even control how they reset (monthly, per billing cycle, or custom).
Let’s say one plan offers:
10 credits
50 video minutes
30 seconds of generative video
And another has:
1000 credits
50 minutes of generative video
You don’t have to create and maintain separate billing logic for every variation. Flexprice tracks each entitlement and enforces the right limits automatically
4. Native support for credit and one-time credits
Flexprice gives you native support for all types of credits; sign-up, promotional, and paid.
You can set recurring monthly or annual credit grants as part of any plan. Whether it’s 2,000 credits per month or a fixed pack per year, they’re automatically added to the customer’s wallet.
Credits roll over between billing cycles with customizable caps, so if you want unused credits to carry forward up to 5,000, you can set the limit.
You can also:
Track all credit types in a unified wallet
Set expiration rules for any credit type (e.g., promo credits expire in 30 days)
Monitor usage and wallet balances in real-time
Define a minimum balance threshold (e.g., top-up when wallet < 100 credits)
Automatically charge and refill the wallet when the threshold is hit
Say you land a 15-month enterprise deal with custom pricing. And within three months they expand and need more seats, so you agree to expand usage.
Five months later, they want to pause a feature, and you renegotiate the contract again. But after eight months they downgraded with new terms and limits. Now, your finance team asks:
Where’s the original contract?
What version are they on?
How should we forecast the revenue this quarter?
With Stripe, you have no native amendment history. When a customer’s contract changes, Stripe doesn’t store the previous state. You can’t track how a plan evolved over time, whether it was upgrades, downgrades, or partial cancellations. Stripe only shows the latest configuration.
For AI and agentic companies, this becomes a problem fast. You might need to:
Reference the original terms for renewals or audits
Calculate revenue accurately across different contract phases
Understand usage in the context of historical entitlements
Without built-in versioning or revenue sync, you’re forced to maintain that history outside Stripe, usually in spreadsheets or custom systems. And that adds unnecessary overhead every time a contract is amended.
