Datadog
Staff AI Engineer - Agent Observability
Boston, MA, United States · New York, NY, United States · Remote · Remote - British Columbia · California, United States
Get past the screening software and onto a recruiter's desk
hirly rewrites your resume for this job — matching the keywords and skills in the posting, moving your most relevant experience to the top, and writing a cover letter to fit. About 30 seconds.
- Keywords matched to this posting
- Fit score before you apply
- Cover letter included
Apply from your AI assistant
Connect hirly to Claude and ask it to apply to this job. hirly tailors your resume, fills the employer’s form and asks before sending. ChatGPT: manual setup today.
Some employer sites stop an application at a CAPTCHA or sign-in and hand it back with a link. Applying needs a paid plan. Works with any assistant that supports MCP.
hirly's read of this role
- Seniority
- Lead / management
- Stated salary
- $234,000 – $300,000 per year
- Countries
- US, CA
- Work mode
- Remote-friendly
- First seen by hirly
- 14 Sept 2026
Derived automatically from the posting. Upload your resume above to see how the role scores against it.
the posting
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 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 .
Listed on hirly, a job board. hirly is not the employer: Datadog is hiring for this role.
Similar jobs
- Sr. Lead - AI EngineerKlaviyo · Boston, MAFirst seen todayremote
- Sr. Principal Software and AI EngineerBeigene · Remote (US)First seen todayremote
- Staff AI EngineerNextiva · United States, RemoteFirst seen todayremote
- Principal AI EngineerJj · Raritan, New Jersey, United States of AmericaFirst seen yesterday
- Staff AI EngineerSecuritas Security Services · Elmsford, NY, United StatesFirst seen yesterday
Browse similar roles
Want this one?
Upload your resume and hirly rewrites it for this job and writes the cover letter — in about thirty seconds, before you sign up.
Tailor my resume for this job