Datadog – Senior Software Engineer (AI) Interview Experience

Result: On Hold (Hiring Freeze)
Number of Rounds: 2 completed

Interview Questions & Experience

Round 1 – Coding: Query Log Matching

Asked to implement a system that dynamically registers queries and matches incoming logs against them, returning matching query IDs. Follow-ups included handling concurrent updates from multiple threads, supporting query deletion, and optimizing memory usage and retrieval speed. Discussed an inverted index approach and started implementing it, but ran out of time.

Round 2 – LLM System Design: Jira-to-PR Agent

Asked to design an AI agent that takes a Jira bug ticket, understands the codebase, generates a fix, validates it, and creates a PR. Follow-ups focused on LLM evaluation, monitoring, improving accuracy, scalability, high availability, and handling failures in production.

Tips & Takeaways

Be prepared for coding questions with concurrency and optimization follow-ups. For LLM system design, focus on production-grade agent architecture, evaluation, observability, reliability, and scaling.