Greenhouse ·
full-timeStaff AI Engineer - Agent Observability
Datadog · Boston, Massachusetts, USA; New York, New York, USA
Datadog is a monitoring and security platform for cloud-scale applications. The Agent Observability team focuses on building tools that allow customers to monitor, trace, and debug AI systems, specifically those utilizing Large Language Models and generative AI. As a Staff AI Engineer, you will lead the design and development of features related to model evaluation, drift detection, and behavior tracing. Your day-to-day responsibilities include architecting scalable backend solutions, prototyping new product capabilities, and collaborating with cross-functional teams including product, UX, and applied science. You will influence technical strategy, mentor other engineers, and translate customer pain points into actionable product improvements. This role is well-suited for an experienced software engineer with a strong background in distributed systems and hands-on experience building or shipping LLM-powered applications. A successful candidate will possess a deep understanding of model internals, inference pipelines, and prompt engineering, alongside the ability to navigate ambiguous, fast-moving technical landscapes to build reliable, high-performance observability tools.
The Agent Observability team builds cutting-edge tools to monitor, explain, and improve AI systems in production, particularly those leveraging Large Language Models (LLMs) and generative AI. We provide robust, scalable observability for AI workloads, including drift detection and model evaluation, and behavior tracing, enabling customers to ship AI with confidence. As a Staff Engineer, you’ll lead the development of new features and foundational capabilities within Datadog’s LLM Observability product. You will shape product direction, drive experimentation, and apply your deep understanding of both AI systems and software engineering to solve open-ended problems in the fast-moving AI landscape. Your work will directly impact how our customers monitor, troubleshoot, and optimize LLM-based applications in production. Join us in building the foundational tools that make AI systems observable, understandable, and reliable in the real world. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do: Drive design and implementation of LLM observability features. Ideate, prototype, and scale new product features to provide insights and drive improvements for generative AI systems Work cross-functionally with other eng teams, product, UX, and applied science to iterate fast and find product-market fit Develop and extend tools for tracing, evaluating, and debugging LLMs Influence architecture decisions and mentor engineers to build resilient, high-performance systems Stay close to customer pain points and use those insights to guide product and engineering priorities Stay current with industry trends and advancements in machine learning and observability, driving innovation within the team Who You Are: You have a BS/MS/PhD in a Computer Science, Engineering or related scientific field or equivalent experience Deep understanding of distributed systems and scalable backend architectures Hands-on experience building and shipping LLM-powered or GenAI applications. Understanding of model internals, inference pipelines, evaluation techniques, and prompt engineering Ability to thrive in ambiguous, fast-changing spaces and have a product-oriented mindset You’re excited to shape the next generation of AI observability tools from the ground up Communicate clearly, think rigorously, and take pride in clean, maintainable code Experience with observability tools/platforms 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. Benefits and Growth: Get to build tools for software engineers, just like yourself. And use the tools we build to accelerate our development. Have a lot of influence on product direction and impact on the business . Work with skilled, knowledgeable, and kind teammates who are happy to teach and learn Competitive global benefits Continuous professional development Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog. #LI-Hybrid Datadog offers a competitive salary and equity package, and may include variable compensation. Actual compensation is based on factors such as the candidate's skills, qualifications, and experience. In addition, Datadog offers a wide range of best in class, comprehensive and inclusive employee benefits for this role including healthcare, dental, parental planning, and mental health benefits, a 401(k) plan and match, paid time off, fitness reimbursements, and a discounted employee stock purchase plan. The reasonably estimated yearly salary for this role at Datadog is: $234,000 — $300,000 USD About Datadog: 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. Equal Opportunity at Datadog: 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. Datadog endeavors to
| Role | Staff AI Engineer - Agent Observability |
|---|---|
| Company | Datadog |
| Location | Boston, Massachusetts, USA; New York, New York, USA |
| Type | full-time |
| Compensation | Not disclosed |
| Posted | 2026-10-13 |
| Deadline | Rolling |
Typical process for this type of role
A general guide — the exact steps for this specific listing may vary; check the original posting for details.
- 1ApplicationSubmit your resume through the apply link.
- 2ScreeningRecruiter reviews your background against the role.
- 3AssessmentA technical test, assignment, or coding round, depending on the role.
- 4Interview(s)One or more rounds with the hiring team.
- 5OfferOffer letter with compensation and start date.
Before you apply
0/4About Datadog
Datadog provides a modern monitoring and security platform designed for developers, IT operations teams, and business users operating in the cloud. The company's platform offers a wide range of capabilities, including infrastructure, network, container, and serverless monitoring, as well as application performance monitoring, log management, and cloud security. These tools are utilized by organizations across various industries, such as financial services, healthcare, retail, and technology, to enable digital transformation and drive collaboration across teams. Datadog employs over 8,100 people globally and continues to expand its presence to support customers across diverse markets and regions.
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