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

SeniorPrefer not to say
Apr 2026Remote

Summary

System design round at OpenAI for a backend role. The whole session was basically one giant calendar design question that branched into like five different sub-problems. Harder than I expected, mostly because the scope kept expanding.

Questions Asked (5)

Q1

Design a calendar service similar to Google Calendar or Apple Calendar, supporting event creation, editing, deletion, recurring events, invitations with RSVPs, reminders, multi-calendar overlays, and time zone handling.

System DesignData ModelingTechnical Trade-offs
Author's notes

The surface area of this question is deceptive.

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AI HintsAI Generated

Suggested Approach

Start by clarifying functional and non-functional requirements, then design the data model and API, focusing on the complexities of recurring events and time zones. Discuss trade-offs between different approaches for recurrence expansion, notification delivery, and consistency, and finally address scalability and reliability concerns.

Pro tip: Emphasize the importance of idempotency and exactly-once semantics for event operations and notifications, as these are critical in a distributed system like a calendar service. Also, consider how to handle conflicts and concurrency, such as when multiple users edit the same event simultaneously.

1. Requirements Clarification

Ask clarifying questions to understand the scope: expected scale (users, events), consistency requirements, supported recurrence patterns, notification channels, and integration needs (e.g., with email).

2. High-Level Design

Outline the main components: API gateway, calendar service, event store, notification service, and external integrations. Sketch the data flow for key operations like event creation and RSVP.

3. Data Modeling and Storage

Design schemas for users, calendars, events, recurrences, invitations, and reminders. Choose appropriate databases (e.g., relational for core data, NoSQL for scalability) and discuss indexing for efficient queries.

4. Deep Dive into Complex Features

Explain how to handle recurring events (e.g., using RRULE, expansion on read vs. write), time zone conversions (store UTC, convert on display), and reminders (scheduling with a delay queue).

5. Scalability, Reliability, and Trade-offs

Discuss partitioning strategies, caching, handling failures, and trade-offs between consistency and availability. Address how to ensure notifications are delivered reliably and how to handle concurrent edits.

Key Points to Mention

  • Recurring events: use of iCalendar RRULE standard, expansion strategies (on-the-fly vs. precomputed), and handling exceptions (e.g., modified instances).
  • Time zone handling: store all times in UTC, convert to user's time zone on display, and handle DST transitions correctly.
  • Invitations and RSVPs: modeling attendees, status tracking, and sending notifications; consider using a separate service for email/SMS.
  • Reminders: scheduling using a distributed delay queue (e.g., Redis sorted sets, RabbitMQ delayed messages) and ensuring idempotent delivery.
  • Multi-calendar overlays: efficient querying to fetch events from multiple calendars within a time range, possibly using a read-optimized store.
  • Scalability and consistency: sharding by user or calendar, caching frequently accessed data, and using eventual consistency for notifications while ensuring strong consistency for event edits.

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

Q2

How would you model recurring events with exceptions, such as skipping or modifying a single occurrence in a repeating series?

Data ModelingTechnical Trade-offsAlgorithms & Data Structures
Author's notes

This is where I spent the most time and probably lost the most points.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements: what types of recurrence (daily, weekly, monthly by day or date), what exceptions (skip, modify, add), and query patterns (range queries, single event lookup). Then propose a data model that separates the recurrence rule from exception overrides, and discuss trade-offs between storing expanded instances vs. computing on the fly. Finally, outline how to handle edge cases like time zones, DST, and infinite recurrence.

Pro tip: Mention that you'd store the recurrence rule in a standard format like iCalendar RRULE and use a library to expand occurrences, but cache or precompute for performance. Also, highlight that exceptions should be stored as overrides keyed by the original occurrence's start time, which simplifies lookups and modifications.

1. Clarify requirements and constraints

Ask about the types of recurrence patterns, exception types (skip, modify, add), query patterns (range vs. single), and scale (number of events, frequency of changes). This ensures the model fits the use case.

2. Choose a representation for the recurrence rule

Use a standard like iCalendar RRULE (RFC 5545) to define the pattern, or design a custom schema if needed. Discuss how to store it (e.g., as a string or structured fields).

3. Model exceptions as overrides

Store exceptions separately, keyed by the original occurrence's start time (or a unique occurrence ID). For skips, mark as cancelled; for modifications, store the changed fields. This avoids duplicating the entire series.

4. Decide on expansion strategy

Compare computing occurrences on the fly (using the rule and exceptions) vs. precomputing and storing instances. Discuss trade-offs: on-the-fly is flexible but may be slow for large ranges; precomputed is fast for reads but requires updates when the rule changes.

5. Address edge cases and operational concerns

Cover time zones, daylight saving time, infinite recurrence (use bounded queries), and how to handle updates to the series (e.g., 'this and future' vs. 'all'). Mention indexing for efficient range queries.

Key Points to Mention

  • Use of iCalendar RRULE (RFC 5545) for recurrence patterns
  • Storing exceptions as overrides keyed by original occurrence start time
  • Trade-offs between on-the-fly expansion and precomputed instances
  • Handling time zones and DST correctly (store in UTC, apply time zone rules)
  • Strategies for querying occurrences in a date range efficiently (indexing, caching)
  • How to handle modifications to the series (e.g., 'this event', 'this and future', 'all events')

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

Q3

Walk through how you'd handle conflict detection when multiple users or devices try to update the same event simultaneously.

System DesignTechnical Trade-offsConflict Resolution
Author's notes

Talked about optimistic locking and vector clocks.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the requirements and constraints, then compare optimistic vs pessimistic concurrency control, and finally propose a concrete solution with trade-offs. Emphasize how you'd handle conflicts in a distributed system, including detection, resolution, and user experience.

Pro tip: Mention that conflict resolution is not just technical but also a product decision—sometimes it's better to merge changes or prompt the user rather than silently overwrite. Also, highlight the importance of idempotency and versioning to avoid duplicate updates.

1. Clarify requirements and assumptions

Ask about the expected concurrency level, consistency requirements, and whether the system is distributed. Clarify if users need immediate feedback or if eventual consistency is acceptable.

2. Choose a concurrency control strategy

Discuss optimistic concurrency control (e.g., version numbers, ETags) vs pessimistic locking. Explain when each is appropriate, considering latency, scalability, and user experience.

3. Design conflict detection and resolution

Describe how to detect conflicts (e.g., version mismatch) and resolve them (e.g., last-write-wins, merge, user prompt). Mention techniques like CRDTs for automatic merging if applicable.

4. Address distributed system challenges

Cover issues like clock skew, network partitions, and consistency models (e.g., strong vs eventual). Explain how to ensure correctness across multiple devices or data centers.

5. Discuss trade-offs and edge cases

Summarize the trade-offs of your approach (e.g., complexity, performance, user experience) and mention edge cases like offline edits or partial failures.

Key Points to Mention

  • Optimistic vs pessimistic concurrency control
  • Versioning (e.g., version numbers, ETags) and idempotency
  • Conflict resolution strategies: last-write-wins, merge, user intervention
  • Distributed systems challenges: clock skew, network partitions, consistency models
  • CRDTs and operational transforms for automatic merging
  • User experience considerations: how to notify users of conflicts and allow resolution

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

Q4

How would you design push-based sync across multiple devices, similar to how CalDAV works, while supporting offline-first behavior?

System DesignAPI & IntegrationsTechnical Trade-offs
Author's notes

Went with a change-log table and per-device sync tokens.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements: multi-device push sync, offline-first, conflict resolution, and scale. Then propose a hybrid architecture using a central sync service with change logs, push notifications, and client-side local databases, explaining how CalDAV principles (resources, ETags, sync-tokens) map to your design. Finally, discuss trade-offs around consistency, latency, and conflict handling.

Pro tip: Emphasize that offline-first means the client is the source of truth for local changes, and the server must reconcile concurrent edits—use vector clocks or version vectors to detect conflicts, and always provide a deterministic merge strategy (e.g., last-write-wins with server timestamp or CRDTs for specific fields).

1. Clarify Requirements and Constraints

Ask about scale (number of devices, users), data types (calendar events, contacts), consistency needs, and whether push must be real-time. Confirm offline-first expectations: clients can read/write without network, and sync when connectivity returns.

2. Design Core Sync Protocol

Propose a RESTful API with resources (e.g., events) identified by URIs, using ETags for optimistic concurrency and a sync-token (like CalDAV's sync-collection) to fetch changes since last sync. Include a change log on the server to track modifications.

3. Implement Push Mechanism

Use WebSockets or long-polling for real-time push notifications to online devices. For offline devices, queue notifications and deliver upon reconnection. Consider using a pub/sub system (e.g., Redis Pub/Sub, Kafka) to fan out changes to connected devices.

4. Handle Offline-First and Conflicts

Clients store data locally (e.g., SQLite) and queue changes. On sync, send local changes with version vectors; server detects conflicts and applies merge policy. Return conflicts to client for resolution if needed, or auto-merge using CRDTs for certain fields.

5. Discuss Trade-offs and Scalability

Compare push vs. pull, consistency models (strong vs. eventual), and conflict resolution strategies. Address scalability: sharding by user, caching, and rate limiting. Mention monitoring and failure recovery.

Key Points to Mention

  • CalDAV concepts: resources, ETags, sync-tokens, and how they enable efficient incremental sync.
  • Push notification mechanisms: WebSockets, SSE, or APNs/FCM for mobile, and how to handle offline devices.
  • Offline-first client architecture: local database, change queue, and sync engine.
  • Conflict detection and resolution: version vectors, last-write-wins, CRDTs, and user-driven merge.
  • Scalability considerations: sharding, pub/sub fan-out, and handling millions of devices.
  • Security and authentication: OAuth, per-device tokens, and encryption in transit.

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

Q5

How would you architect the notifications and reminders system to scale to billions of events?

System DesignTechnical Trade-offs
Author's notes

Honestly the part I felt best about.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements (scale, latency, delivery guarantees, channels) and then propose a distributed, event-driven architecture that decouples ingestion from delivery. Focus on partitioning, idempotency, and backpressure to handle billions of events, and discuss trade-offs between consistency and availability.

Pro tip: Emphasize the importance of idempotency and deduplication at scale, and mention how you would handle failures gracefully with retries and dead-letter queues to avoid notification storms.

1. Clarify Requirements and Constraints

Ask about expected event volume, latency SLAs, delivery guarantees (at-least-once, exactly-once), supported channels (email, push, SMS), and user preferences. This ensures the design meets actual needs.

2. High-Level Architecture

Propose an event-driven pipeline: ingestion via API/gateway, message queue (e.g., Kafka) for buffering, stream processing for filtering/aggregation, and a delivery service that dispatches to providers. Use a separate scheduler for reminders.

3. Scaling and Partitioning

Explain how to partition data by user ID or event type to distribute load, use sharding for the database, and scale consumers horizontally. Discuss how to handle hot partitions and ensure even distribution.

4. Reliability and Fault Tolerance

Describe mechanisms for idempotency (deduplication keys), retries with exponential backoff, dead-letter queues for failed deliveries, and monitoring/alerting. Ensure no single point of failure.

5. Trade-offs and Optimizations

Discuss trade-offs between latency and throughput, consistency vs. availability, and cost. Mention optimizations like batching, rate limiting, and using CDNs for static content.

Key Points to Mention

  • Event-driven architecture with message queues (e.g., Kafka, Pulsar) for decoupling and buffering
  • Partitioning strategies (by user ID, event type) to scale horizontally and avoid hotspots
  • Idempotency and deduplication to handle at-least-once delivery and prevent duplicate notifications
  • Backpressure and rate limiting to protect downstream services and providers
  • Scheduling for reminders: use a distributed scheduler (e.g., Quartz, cron-based) with persistent storage
  • Monitoring, alerting, and dead-letter queues for failure handling and observability

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