Senior Software Engineer, AI Platform - Evaluation & Annotation

The AI Platform team at Datadog builds the infrastructure that powers the next generation of generative AI features across our products.

As a Senior Software Engineer on the Evaluation and Annotation team, you will design and evolve the systems that define and measure AI quality at scale. This includes building evaluation pipelines, model performance monitoring, and annotation workflows that assess correctness, safety, bias, and reliability across production use cases.

Your work will directly shape how Datadog ships and maintains trustworthy AI capabilities. You will partner closely with product, ML, and infrastructure teams to define quality standards, integrate evaluation systems with our observability platform, and build human-in-the-loop feedback mechanisms that continuously improve model behavior.

At Datadog, we place value in our office culture - the relationships that it builds, the creativity it brings to the table, and the collaboration of being together. We operate as a hybrid workplace to ensure our employees can create a work-life harmony that best fits them.

• →Design and scale robust evaluation systems to measure the performance and reliability of LLMs and AI agents across Datadog’s product ecosystem
• →Lead efforts to build human-in-the-loop and automated annotation pipelines for model assessment, ensuring high-quality training and feedback data
• →Define and implement continuous evaluation workflows in CI/CD and production environments to monitor model behavior in real time
• →Analyze model outputs for correctness, bias, safety, and reliability and translate insights into actionable improvements
• →Collaborate cross-functionally with Applied Scientists, Researchers, product managers, and platform engineers to establish best practices for responsible AI
• →Mentor team members and contribute to long-term technical strategy focused on AI quality, trust, and safety

• You have 6+ years of experience building large-scale distributed systems or machine learning systems in production environments
• You’ve designed infrastructure to support AI/ML model evaluation, annotation, or benchmarking workflows
• You approach engineering with a focus on system design, long-term maintainability, and reliability
• You bring a strong understanding of AI/ML concepts, including evaluation metrics, prompt analysis, and trust & safety challenges
• You thrive in cross-functional teams and communicate effectively with technical and non-technical stakeholders
• You have demonstrated ability to use AI coding tools in day-to-day workflows and validate, critique, and refine AI-generated output.
• Bonus: you’re motivated to push the boundaries of how AI can improve software engineering best practices and contribute to building AI-enabled products.
• Bonus: you’ve used open-source tools like evaluation frameworks (e.g., lm-eval-harness), vector databases, or human feedback loops

Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your skills, we encourage you to apply.

Datadog is the leading observability and security platform for the AI era, providing businesses with unified visibility across the technology stack to manage complexity at scale. It brings applications, infrastructure, data, models, and security into one place, using AI to detect and resolve issues before they impact customers. Trusted globally by Fortune 500 companies and high-growth AI leaders, Datadog enables businesses to move faster with clarity and confidence. Learn more about #DatadogLife on Instagram, LinkedIn, and Datadog Learning Center.

Datadog is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and other characteristics protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. Here are our Candidate Legal Notices for your reference. 

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