Staff AI Engineer - Agent Observability
Datadog is hiring a Staff AI Engineer - Agent Observability in Boston and New York, United States. It pays $234k-$300k a year and Level rates it ; you can apply on Level.
AI in this role
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 USDAbout 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 make our Careers Page accessible to all users. If you would like to contact us regarding the accessibility of our website or need assistance completing the application process, please complete this form. This form is for accommodation requests only and cannot be used to inquire about the status of applications.
Privacy and AI Guidelines:
Any information you submit to Datadog as part of your application will be processed in accordance with Datadog’s Applicant and Candidate Privacy Notice. For information on our AI policy, please visit Interviewing at Datadog AI Guidelines.
How we rate this
Staff AI Engineer - Agent Observability at Datadog rates 91 out of 100 for how much of the daily work is AI. That makes it Builds AI (AI Level 4 of 4). The level is about AI in the job, not seniority.
Builds AI. The job is building AI systems.
- ●●●● Builds AI80 to 100
- ●●●○ Works on AI60 to 79
- ●●○○ Uses AI40 to 59
- ●○○○ Little AI0 to 39
Levels come from how often the tools, models and workflows of the role are named in the posting itself. Open the description and count.
Prepare for this job
Built from this posting and from similar jobs on Level.
Skills and AI tools this role asks for
Pay
- This job starts at
- $234k
- Typical AI engineer job
- $180k
This posting starts 30% above the typical AI engineer job. See AI engineer jobs
Questions you could be asked
- How do you structure and test a prompt to get consistent output from a language model?
- How do you decide that one model's output is better than another's for a given task?
- How would you decide a model or AI system is ready to ship?
- Tell me about a time a model underperformed in production. How did you find out, and what did you change?
Adapt your resume
- List these exact terms on your resume: Prompt engineering and AI Evaluation. An applicant tracking system matches the wording, not the idea.
- Attach one line of real, concrete experience to at least one of them. A tool named with nothing behind it rarely survives a human read.
- Lead with what you built, trained or shipped. This role is judged on the AI system itself, not the tools around it.
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