Prompt
Can you recommend a subscription billing platform for managing trials, recurring billing, and failed payment recovery for an online course business?
Latest observation
Yes — for an online course business, I’d look at Chargebee, Stripe Billing, or Recurly depending on how much you want out-of-the-box vs. how customizable you need it to be.
Best overall for most course businesses: Chargebee
Why it fits:
- Handles free/paid trials
- Supports recurring subscriptions
- Built-in failed payment recovery / dunning
- Good for coupons, upgrades/downgrades, pauses, and plan changes
- Integrates well with popular payment processors and CRMs
- Better “subscription business” features than using payment processing alone
Good if: you want a mature subscription platform without building everything yourself.
Best if you want a lightweight, developer-friendly stack: Stripe Billing
Why it fits:
- Excellent for trial management
- Strong recurring billing and proration support
- Solid failed payment recovery tools
- Easy if you already use Stripe for payments
- Great APIs and checkout flows
Tradeoff: more flexible, but you may need to assemble more of the subscription workflow yourself.
Good if: you’re technical or already deeply in Stripe.
Best for advanced revenue operations: Recurly
Why it fits:
- Strong dunning / recovery
- Good subscription lifecycle management
- Supports complex billing logic
- Often used by larger subscription businesses
Tradeoff: can be more than a small course business needs.
Good if: you expect more complex billing rules or scale.
My practical recommendation
For an online course business, I’d usually choose:
- Chargebee if you want the best balance of features and ease
- Stripe Billing if you want simpler infrastructure and can customize
- Recurly if billing complexity is likely to grow
Features to make sure you have
Whatever platform you choose, confirm it supports:
- Free trials with automatic conversion
- Retry logic for failed payments
- Card updater / expired card handling
- Dunning emails and recovery workflows
- Coupons / promotions
- Pause, cancel, upgrade, downgrade
- Integration with your LMS / course platform
- Tax handling if you sell internationally
If you want, I can also give you a short comparison table of Chargebee vs Stripe Billing vs Recurly specifically for course businesses, or recommend based on your stack (e.g., Teachable, Kajabi, Webflow, WordPress, custom site).