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OpenAI interview notes, page 37 of 67

Mid-sized

Most of these OpenAI write-ups come from Software Engineers (460), then Machine Learning Engineers (137) and Backend Engineers (23). The most reported rounds are the technical phone screen (335), the system design round (229), the onsite coding round (32) and the behavioral / leadership round (22).

667 interview notes · updated Jul 2026

OpenAI·Software Engineer·Technical Phone Screen

May 2026
OpenAI software engineer interview where the main challenge was building a working interpreter for a toy language from scratch, including tokenizing, parsing, and evaluating it live on the spot. The follow-up extensions made it way harder than the initial prompt suggested.
  • Implement a parser and interpreter for a small toy language that supports variable assignment, arithmetic expressions, basic control flow, and print statements. Tokenize the input, build some form of AST or evaluate inline, and execute the program correctly.

“This wrecked me a little.”

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OpenAI·Machine Learning Engineer·Onsite - System Design / Architecture

May 2026
System design round at OpenAI for an ML Engineer role, focused entirely on near-duplicate media detection at scale. The problem was meaty and I felt like I was mostly keeping my head above water the whole time.
  • Design a system to detect near-duplicate images and videos at massive scale, including reuploads, minor edits, re-encodes, and watermarked versions.

“This is basically the whole interview in one question.”

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OpenAI·Software Engineer·Onsite - System Design / Architecture

May 2026
System design round at OpenAI focused almost entirely on payments and reconciliation. The scope was narrow on paper but the depth they wanted was pretty intense, especially around the ledger model and how you handle async settlement files from PSPs.
  • Design an end-to-end payment system with a focus on reconciliation. How do you ensure what your system recorded matches what the payment processor or bank reports?
  • Walk through the data model for a double-entry ledger in a payment system. How does it support accurate financial tracking?
  • How would you design idempotency keys for payment operations to handle retries safely?
  • Describe the status state machine for a payment transaction, from initial creation through to final settlement, refund, or failure.
  • How do you process asynchronous settlement files from payment processors and reconcile them against your internal records?
  • How would you detect and handle mismatches between your internal payment records and external processor reports?
  • What retry and compensation strategies would you use when a payment operation fails or a reconciliation mismatch can't be auto-resolved?

“This is a big question and I made the mistake of spending too long on the happy path.”

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OpenAI·Software Engineer·Technical Phone Screen

May 2026
Interviewed for a software engineering role at OpenAI. Just one question but it covered a lot of ground, basically a full project deep-dive that touched on everything from technical decisions to personal impact.
  • Walk me through a recent project: what were the goals, what did you personally contribute, how did you approach it technically, what trade-offs did you make, and what was the outcome?

“This felt like five questions stitched into one and I kind of fumbled the sequencing.”

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OpenAI·Software Engineer·Onsite - System Design / Architecture

May 2026
Interviewed for an EM role at OpenAI and got hit with a classic system design question. Not much to report beyond that, but it was a solid exercise in thinking through scale and product constraints at the same time.
  • Design a messaging and collaboration platform like Slack.

“I jumped straight into the data model and real-time messaging layer, which felt right, but I spent too long on WebSocket connection handling and barely touched the workspace/channel permission model.”

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OpenAI·Machine Learning Engineer·Technical Phone Screen

May 2026
Interviewed for an ML Engineer role at OpenAI and got hit with a multi-head attention implementation question from scratch. Pretty deep on the theory side, not just a vibe check.
  • Implement multi-head attention from scratch using NumPy or PyTorch.

“I knew this was coming eventually but still fumbled the scaling factor for a second.”

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OpenAI·Software Engineer·Technical Phone Screen

May 2026
Interviewed for a full-stack role at OpenAI and got a system design question about building a multi-bot chat dispatcher. Pretty interesting problem, more software architecture than pure algorithms, which I wasn't fully expecting.
  • Design and implement a chat system with multiple bots (e.g. one that responds to keywords, one that books meetings, one that auto-replies for away users). Incoming messages should be dispatched to all registered bots, each bot can return zero or more responses, and adding new bots later should be straightforward.

“My first instinct was to just write a big if-else block and I'm glad I caught myself before saying that out loud.”

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OpenAI·Machine Learning Engineer·Onsite - System Design / Architecture

May 2026
System design round at OpenAI for an ML Engineer role, focused entirely on building a RAG system end to end. Pretty intense scope, they wanted you to cover everything from chunking strategy to eval pipelines to online monitoring, not just the happy path architecture.
  • Walk me through how you'd design a RAG system end to end for answering questions over a private document corpus.
  • How would you handle document ingestion and preprocessing, specifically parsing, cleaning, and chunking strategy?
  • What embedding strategy would you use, and how would you set up the index? Would you use pure vector search or something hybrid?
  • How would you approach retrieval, including query understanding, choosing top-k, and filtering? Would you add a reranking step?
  • How do you handle cases where retrieval is weak or returns irrelevant context? What guardrails or fallback behavior would you build in?
  • Describe your evaluation plan across the full pipeline: chunking quality, retrieval quality, reranking, generation grounding, and overall user success.
  • How would you set up online monitoring and a continuous improvement loop for a deployed RAG system?
  • How would you design the system to support frequent document updates, like new or changed docs, without degrading retrieval quality?

“This is the kind of question where you think you know what to say and then realize mid-sentence you're already in the weeds.”

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OpenAI·Software Engineer·Onsite - System Design / Architecture

May 2026
System design round at OpenAI for a software engineer role. The interviewer kept pushing with follow-ups after every answer, which made it feel less like a conversation and more like a stress test.
  • Design a payment system.

“The base question is manageable but the follow-ups were relentless.”

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OpenAI·Machine Learning Engineer·Technical Phone Screen

May 2026
Coding round at OpenAI for an ML Engineer role, one problem that looked like a simple binary search until it really wasn't. The time limit on the 'Interesting' test cases is brutal and a flat search just doesn't cut it.
  • You have a sorted list of semantic version strings and a function isWorking(version). Find any working version efficiently, knowing the version space is hierarchical (major.minor.patch) and each axis is monotone with respect to the working predicate. Some versions may be missing patch or minor components. Your solution must pass Simple, Large, and Interesting test case categories within the time limit.

“I went straight for binary search on the flat list and it passed Simple and Large.”

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