“We could just build this in Retool...” — Every startup, right before creating a second product with an infinite roadmap that no one wants to maintain.
Here’s how that typically plays out:
Step 1: Add usage tracking + flags “Let’s just track completions and projects + gate access with a flag” → 1–2 weeks of dev time → Already diverging from roadmap
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Step 2: Build basic Stripe sync + Retool admin panel “We need to create plans and manage who’s on what” → Fragile logic, no true entitlement model → Manual workarounds for upgrades, trials
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Step 3: Build a customer portal “We need users to see usage, manage plans, and upgrade” → React components, billing UI, prorations → Deep Stripe integration, edge cases, customer support
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Step 4: Sales needs help to close deals “Smaller deals need trials. Larger deals need custom plans.” → Custom logic for discounts, free credits, enterprise plans → Now GTM is blocked by engineering
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Step 5: Product led growth for both new and expansion revenue: overages, alerts, and credits “The product should drive revenue and build pipeline” → Webhooks, alerting, expansion triggers → More complexity, more maintenance
Total cost: months of engineering time + ongoing support
Bottom line: Billing & monetization infrastructure always starts small — and becomes an unmaintained shadow product.
Schematic lets you skip the debt and move fast.That’s why companies like Zep, BlackCloak, TighKnit, and Plotly chose to buy rather than build.
True Stories: In 2022, Contentful spent $3M and 2 years decoupling entitlements from billing. In 2023, BlackCloak spent “hundreds of thousands of dollars on core dev resources reinventing the wheel around billing and packaging.
Companies ranging from pre-launch to seed to enterprise are rethinking their approach to monetization so that they avoid hardcoded pricing implementations that drive technical and commercial debt.
