Senior Design Manager - AI Monitoring & Management

This team owns what it takes for an organization to trust the AI it runs in production, from the GPU infrastructure that trains and serves models, to the agents and LLM systems built on top of it, to the cost and return those systems deliver to the business. When something fails, this team's work explains why and shows how it's affecting the outcomes customers actually care about. It's a fast-moving space with few established patterns, which gives this team real room to define what best-in-class looks like.

As Senior Design Manager, you'll lead a team of four designers across these three connected product areas, going deep enough on the domain (AI training and development workflows, evaluations, GPU infrastructure, agent debugging) to raise the quality bar, sharpen the product point of view, and mentor the team already doing this work. This is a leadership role built around modern, AI-native design practice: you'll lead and grow a team that builds directly in code rather than handing off static mocks, and you should have the capability to prototype and ship yourself where it has the most impact.

What You'll Do:

• Go deep on the domain (AI training/development workflows, evals, GPU infrastructure, agent debugging) to the point of having independent, well-informed points of view
• Drive end-to-end product experiences across Agent Observability, GPU Monitoring, and Agent Console, ensuring coherence across the three surfaces
• Prototype and ship directly in code where it has the most impact, to demonstrate direction and quality, not as a substitute for the team's own execution
• Lead and coach a team of four designers, raising their craft, product thinking, and fluency building with AI-native tools
• Conduct regular 1:1s and career conversations; foster psychological safety and a culture of continuous improvement
• Partner with Product and Engineering leadership to shape strategy, prioritization, and roadmap direction
• Set and maintain a high bar for design quality across all output, including interaction design, visual design, coded prototypes, and user testing, and lead design critiques within the domain

Who You Are:

• 10+ years in product design roles, with 3+ years in a design management or leadership position
• Portfolio demonstrating end-to-end product design ownership and deep domain expertise in at least one complex area
• Demonstrated ability to take an existing product area and visibly uplevel its craft and product ownership
• Strong communication and influence skills; able to partner effectively with senior-level PMs and Engineers
• Experience designing complex, data-heavy products
• Capability to prototype and ship directly in code (Claude Code, Cursor, or similar), and comfort leading a team that works the same way
• Demonstrated ability to mentor designers and raise their craft through coaching and example
• Nice to have: experience designing developer tools, AI/ML products, or observability platforms, and comfort with ambiguity in a rapidly evolving space

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:

• New hire stock equity (RSUs) and employee stock purchase plan (ESPP)
• Continuous professional development, product training, and design education
• Intradepartmental mentor and peer coaching program
• Inclusive company culture; access to Datadog Community Guilds (employee resource groups)
• Free, global mental health benefits for employees and dependents age 6+
• Competitive global benefits

Benefits and details may vary based on country of employment and employment nature with Datadog.

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.

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. 

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