Head of Cloud Observability Engineering

PVH (Tommy Hilfiger/Calvin Klein); Boston (MA); Hybrid; USD 296,000 - 370,000; Full time

Benefits offered by this job

RSUs

ESPP

Career development

Job summary

Datadog is seeking a Director to own engineering for Cloud Observability, overseeing a large team across NYC, Boston, and Paris. You will shape the roadmap with product leadership, drive AI adoption, and coordinate dependencies between multiple groups to deliver scalable observability solutions.

You have a proven track record managing Engineering Managers, operating large-scale cloud systems, and balancing cost with performance.

Qualifications

• Experience leading managers of managers and large teams.
• Strong cloud provider experience and operating large scale cloud systems.
• Solid understanding of cloud economics and cost-performance tradeoffs.
• AI-first thinking integrated into leadership and engineering practices.
• Track record shaping product decisions, not just executing specs.
• Experience with data-intensive or high-throughput backend systems.

Responsibilities

• Own engineering for Cloud Observability and related platforms.
• Manage ~40 engineers through a layer of Engineering Managers.
• Shape the roadmap with product leadership, drive strategy.
• Lead AI adoption across tooling, workflows, and features.
• Coordinate cross-team dependencies across multiple groups.
• Build and retain engineering talent in NYC, Boston, and Paris; mentor EMs.
• Participate in on-call rotation and strategic reviews.

Skills

Engineering Management

Cloud providers

AI adoption

Cloud economics

Leadership strategy

English fluency

Education

Bachelor's degree in CS

Tools

AWS

Azure

GCP

Job description

Datadog is seeking a Director to own engineering for Cloud Observability, overseeing a large team across NYC, Boston, and Paris. You will shape the roadmap with product leadership, drive AI adoption, and coordinate dependencies between multiple groups to deliver scalable observability solutions.

You have a proven track record managing Engineering Managers, operating large-scale cloud systems, and balancing cost with performance.