SDE2 Interview Questions at Stripe

Design Stripe's webhook delivery system. Stripe sends millions of webhooks per day to customer endpoints that can be slow, down, or buggy. Cover: at-least-once delivery guarantees, retry with exponential backoff, ordering guarantees (or lack thereof), how to handle a customer endpoint that is down for 24h, and the dead-letter strategy.

Design Stripe's fraud detection system. For every payment, you must decide accept/decline in under 100ms using hundreds of signals. Cover: feature engineering, real-time ML scoring, rule engine, and how you minimise false positives (declined legitimate payments).

Explain how Stripe handles exactly-once payment processing. A customer clicks "Pay" twice in quick succession. How does Stripe prevent double-charging? Walk through idempotency keys in the API, database-level constraints, and how the client should handle the case where the first request times out.

Design Stripe's subscription billing system (Stripe Billing). Customers are charged on recurring intervals (monthly/annual) in different currencies, with proration for plan upgrades. Cover: invoice generation, dunning for failed payments, and SCA (Strong Customer Authentication) compliance.

Explain PCI-DSS compliance requirements for handling card data. What is tokenisation? How does Stripe use it to ensure raw card numbers never touch customer servers? What are the implications for your API design?

Stripe is known for extremely high engineering standards ("move carefully and fix things"). Describe a time you pushed back on a deadline to ensure correctness. Was it the right call?