AI Observability Design Lead

Datadog, Inc.; New York (NY); On-site; USD 204,000 - 255,000; Full time

Benefits offered by this job

RSUs

ESPP

Professional development

Mentor program

Inclusive culture

Mental health benefits

Global benefits

Job summary

Datadog, Inc. is seeking a Senior Design Manager to lead a four-person design team focused on AI training workflows, GPU infrastructure, and agent debugging.

You will craft independent design viewpoints, ship directly in code where impactful, and mentor the team to raise their craft and product thinking. This role partners with Product and Engineering to shape strategy and roadmaps, maintaining high-quality design across surfaces.

Qualifications

• 10+ years in product design with 3+ years in design leadership.
• Portfolio shows end-to-end design ownership in complex domains.
• Ability to prototype and ship in code (Claude Code, Cursor) and lead a team using AI-native tools.

Responsibilities

• Go deep on AI training and development workflows to form independent design viewpoints.
• Drive end-to-end experiences across Agent Observability, GPU Monitoring, and Agent Console.
• Prototype and ship directly in code where it adds impact.
• Lead and coach a team of four designers to raise craft and product thinking.
• Conduct regular 1:1s and career conversations to foster growth.
• Partner with Product and Engineering to shape strategy and roadmap direction.
• Set a high bar for design quality across interaction, visual design, coded prototypes, and user testing.

Skills

Product design leadership

Portfolio

Prototype in code

Mentoring designers

Stakeholder influence

Data-heavy design

Developer tools experience

Tools

Claude Code

Cursor

Job description

Datadog, Inc. is seeking a Senior Design Manager to lead a four-person design team focused on AI training workflows, GPU infrastructure, and agent debugging.

You will craft independent design viewpoints, ship directly in code where impactful, and mentor the team to raise their craft and product thinking. This role partners with Product and Engineering to shape strategy and roadmaps, maintaining high-quality design across surfaces.