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Openai·Backend Engineer·Onsite - System Design / Architecture·Senior

SeniorPrefer not to say
Jun 2026

Summary

System design round at OpenAI for a backend engineer role. The whole thing was focused on one big problem: designing a webhook delivery service end to end. Dense topic with a lot of moving parts, and I felt like I was constantly playing catch-up as the scope kept expanding.

Questions Asked (4)

Q1

Design a webhook delivery system where customers can register HTTP endpoints to receive event notifications, with at-least-once delivery, signed payloads, retries with exponential backoff, a dead-letter queue, and tenant isolation.

System DesignAPI & IntegrationsTechnical Trade-offs
Author's notes

This was basically the whole interview.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements and scale, then design the core components: event ingestion, subscription management, delivery workers, and persistence. Walk through the delivery flow, emphasizing at-least-once semantics, retry logic with exponential backoff, dead-letter queue, and tenant isolation. Finally, discuss trade-offs and operational considerations like monitoring and security.

Pro tip: Highlight idempotency and deduplication strategies for consumers, as at-least-once delivery means duplicates are possible. Also, mention the importance of isolating tenants at every layer (data, compute, network) to prevent noisy neighbor issues.

1. Clarify Requirements and Scale

Ask about expected event volume, number of tenants, latency requirements, and payload sizes. This informs architectural decisions like partitioning and queue choices.

2. Design Core Components

Outline the main services: API for subscription management, event ingestion service, delivery workers, and storage for events, subscriptions, and delivery status. Consider using a message queue for decoupling.

3. Detail Delivery Guarantees and Retries

Explain how at-least-once delivery is achieved with persistent queues and acknowledgments. Describe retry mechanism with exponential backoff and jitter, and how failures are moved to a dead-letter queue after max attempts.

4. Address Security and Tenant Isolation

Discuss signing payloads with HMAC or asymmetric keys, and how tenants are isolated in data storage, processing, and rate limiting to ensure fairness and security.

5. Discuss Trade-offs and Operations

Cover trade-offs like synchronous vs asynchronous delivery, push vs pull, and operational aspects: monitoring, alerting, replay capabilities, and scaling workers.

Key Points to Mention

  • At-least-once delivery semantics and idempotency keys for deduplication
  • Exponential backoff with jitter to avoid thundering herd
  • Dead-letter queue for poison messages and manual inspection
  • Payload signing (e.g., HMAC-SHA256) and verification by consumers
  • Tenant isolation via separate queues, databases, or namespaces
  • Monitoring delivery success rates, latency, and retry counts

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q2

How would you design the worker pool and queue structure to support high throughput while maintaining ordering guarantees per subscription?

System DesignTechnical Trade-offs
Author's notes

Tricky because ordering and throughput are basically in tension.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements: throughput targets, ordering scope (per subscription), and failure semantics. Then propose a partitioned queue architecture where each subscription maps to a dedicated partition, and workers process partitions in parallel while preserving order within each partition. Discuss trade-offs between strict ordering and throughput, and how to handle scaling, rebalancing, and fault tolerance.

Pro tip: Emphasize that ordering guarantees are per subscription, so you can shard by subscription ID to achieve parallelism without violating order. Also, mention that you'd use a pull-based model with long polling or streaming to reduce latency and avoid overwhelming workers.

1. Clarify Requirements and Constraints

Ask about expected throughput, latency SLAs, ordering scope (per subscription), message size, and failure handling. This ensures your design aligns with actual needs.

2. Design Queue Structure with Partitioning

Propose a partitioned queue where each subscription is assigned to a partition (e.g., using consistent hashing). This allows parallel processing across subscriptions while maintaining order within each.

3. Design Worker Pool and Assignment

Use a pool of workers that pull from partitions. Ensure each partition is processed by only one worker at a time to preserve order. Consider dynamic scaling and rebalancing when workers join/leave.

4. Address Fault Tolerance and Exactly-Once Semantics

Discuss checkpointing offsets, idempotent processing, and handling worker failures. Ensure that on failure, the partition is reassigned and processing resumes from the last committed offset.

5. Discuss Trade-offs and Optimizations

Compare strict ordering vs. throughput, and mention techniques like batching, pipelining, and backpressure. Also, consider using existing systems (e.g., Kafka, Pulsar) vs. building custom.

Key Points to Mention

  • Partitioning by subscription ID to enable parallelism while preserving per-subscription order
  • Single worker per partition at a time to maintain ordering
  • Offset management and checkpointing for fault tolerance
  • Dynamic scaling and rebalancing of partitions across workers
  • Backpressure and flow control to prevent overload
  • Trade-offs between strict ordering and throughput, and potential use of existing message brokers

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q3

How would you handle consumer-side idempotency so that retried webhook deliveries don't cause duplicate processing on the receiving end?

API & IntegrationsTechnical Trade-offs
Author's notes

Talked about including a unique delivery ID in the payload header so consumers can dedup on their side.

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AI HintsAI Generated

Suggested Approach

Start by clarifying that idempotency on the consumer side is about ensuring that processing a webhook multiple times has the same effect as processing it once. Then outline a concrete strategy: use a unique idempotency key from the webhook (e.g., event ID) to detect duplicates, store processed keys with a TTL, and make the processing logic idempotent or transactional. Finally, discuss trade-offs like storage cost, race conditions, and failure handling.

Pro tip: Mention that idempotency keys should be stored atomically with the side effects (e.g., in the same database transaction) to avoid race conditions where two retries slip through. Also, highlight the importance of a well-defined retention policy for idempotency keys to balance storage cost and deduplication window.

1. Clarify the goal and constraints

Explain that the goal is to prevent duplicate side effects from retried webhook deliveries, and note constraints like at-least-once delivery, potential out-of-order events, and the need for scalability.

2. Choose an idempotency key

Identify a unique identifier from the webhook payload (e.g., event ID, delivery ID) or derive one from the payload. Ensure it's stable across retries and unique per logical event.

3. Implement deduplication with atomicity

Use a persistent store (e.g., database, Redis) to record processed keys. Ensure the check-and-set is atomic, ideally within the same transaction as the side effects, to avoid race conditions.

4. Handle failures and retries gracefully

If processing fails, ensure the idempotency key is not marked as processed so that retries can succeed. Consider using a two-phase approach or transactional outbox pattern.

5. Discuss trade-offs and operational concerns

Talk about TTL for idempotency keys, storage costs, monitoring for duplicate rates, and how to handle key collisions or missing keys.

Key Points to Mention

  • At-least-once delivery semantics and why idempotency is necessary
  • Using a unique event ID from the webhook as the idempotency key
  • Atomic check-and-set operations to prevent race conditions
  • Storing idempotency keys with a TTL to manage storage growth
  • Making the processing logic idempotent or using transactions
  • Monitoring and alerting on duplicate processing attempts

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q4

Walk through your approach to securing webhook payloads, including signature verification and rate limiting per tenant.

API & IntegrationsSystem Design
Author's notes

HMAC signatures with a shared secret per subscription, include a timestamp in the signed payload to prevent replay attacks.

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AI HintsAI Generated

Suggested Approach

Start by framing webhook security as a multi-layered problem: authentication via HMAC signatures, replay protection, and per-tenant rate limiting. Then walk through a concrete design that covers key management, verification flow, and tenant isolation, emphasizing trade-offs and failure modes.

Pro tip: Mention that you verify signatures using a constant-time comparison and that you store per-tenant secrets in a secure vault with rotation support. Also, highlight that rate limiting should be applied at the edge (e.g., API gateway) and enforced per tenant to prevent noisy neighbors.

1. Clarify requirements and threat model

Ask about expected payload sizes, latency requirements, and whether tenants can have multiple endpoints. Identify threats: spoofing, replay, DoS, and cross-tenant interference.

2. Design signature verification

Use HMAC-SHA256 with a per-tenant secret. Include timestamp and nonce in the signed payload to prevent replay. Verify signature in constant time and reject if timestamp is outside a tolerance window.

3. Implement per-tenant rate limiting

Apply rate limits based on tenant ID, using a sliding window or token bucket algorithm. Enforce at the edge (e.g., API gateway) and consider burst allowances. Return 429 with Retry-After header.

4. Ensure tenant isolation and key management

Store secrets securely (e.g., AWS Secrets Manager) with rotation. Ensure that verification and rate limiting are scoped per tenant to avoid cross-tenant impact. Log failures for auditing.

5. Discuss monitoring and failure handling

Monitor signature failures and rate limit hits. Implement alerting for anomalies. Gracefully handle failures: return appropriate status codes and avoid leaking information.

Key Points to Mention

  • HMAC-SHA256 signature verification with constant-time comparison
  • Replay attack prevention using timestamp and nonce
  • Per-tenant secret management and rotation
  • Rate limiting algorithms (token bucket, sliding window) and per-tenant enforcement
  • Edge enforcement (API gateway) for rate limiting and signature verification
  • Monitoring, logging, and alerting for security events

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.