Role Overview

Datadog's Applied AI group is revolutionizing cloud observability through natural language query (NLQ) and Command-I (Cmd-I) interfaces. As Engineering Manager I - Applied AI in New York, you'll lead teams building LLM-powered systems that enable users to query telemetry data, troubleshoot production issues, and configure Datadog using conversational AI. This role combines technical leadership in natural language processing, retrieval-augmented generation (RAG), and agentic architectures with people management in a fast-paced cloud monitoring environment.

Datadog powers modern cloud applications with comprehensive observability, security, and AI-driven insights. Your work will transform how DevOps teams interact with infrastructure monitoring, application performance, and security telemetry through intelligent conversational agents.

Key Responsibilities at Datadog

• Lead and develop engineering teams building NLQ translation systems, conversational agents, and AI-powered interfaces for cloud observability
• Own end-to-end delivery of natural language capabilities spanning semantic understanding, contextual retrieval, query generation, and agentic reasoning
• Build data flywheels that capture user interactions to continuously improve model performance and create competitive moats
• Drive rigorous AI evaluation frameworks including offline benchmarks, online metrics, and drift detection pipelines
• Collaborate with product managers to integrate AI capabilities across Datadog's observability platform
• Navigate complex trade-offs in LLM systems: accuracy vs latency vs cost vs safety
• Support engineer career growth through coaching, feedback, and fostering innovation culture
• Drive operational excellence, system reliability, and technical quality in production AI systems
• Participate in hiring top AI/ML talent and shape organizational structure

Qualifications & Requirements

• Technical leadership in AI/ML/NLP with proven experience shipping LLM-powered products
• Deep expertise in large language models, RAG systems, semantic search, or agentic architectures
• Experience managing engineering teams in fast-moving AI environments
• Strong product thinking: building systems that compound value through data feedback loops
• Familiarity with AI evaluation methodologies - both offline and online metrics
• BS/MS/PhD in Computer Science, Machine Learning, or equivalent experience
• Comfortable with probabilistic AI systems and rapid experimentation cycles

Datadog welcomes candidates passionate about AI and observability who may not meet every qualification. We prioritize growth mindset and technical potential.

Salary & Benefits

Engineering Manager I - Applied AI roles at Datadog offer competitive total compensation packages. Base salary ranges from $220,000 - $320,000 USD depending on experience, plus significant equity through RSUs and ESPP. Additional benefits include:

• New hire stock equity and employee stock purchase plan
• Global Spring Health benefits for employees and dependents age 6+
• Continuous professional development and career pathing
• Inclusive Community Guilds and employee resource groups
• Competitive global benefits package
• Product training across observability, security, and AI
• Hybrid workplace flexibility in New York
• Corporate giving programs

Why Join Datadog?

Datadog leads cloud observability with 15,000+ customers including 70% of Fortune 500. Our Applied AI team pioneers conversational interfaces that make complex telemetry accessible through natural language. Work with bleeding-edge LLMs, build data moats, and scale AI systems serving petabytes of monitoring data daily.

New York office fosters collaboration in a hybrid model balancing office culture with work-life harmony. Join a people-first engineering culture emphasizing experimentation, rapid iteration, and technical excellence.

How to Apply

Ready to lead AI innovation at the intersection of observability and conversational AI? Apply now for Manager I, Engineering - Applied AI in New York. Datadog's hiring process includes technical interviews focused on AI systems design, leadership case studies, and cultural fit. We move quickly for exceptional candidates passionate about transforming cloud monitoring through natural language interfaces.

Keywords: Datadog AI careers, NLP engineering manager, LLM product leadership, cloud observability jobs New York, conversational AI roles