Datadog for Startups - Forward Deployed Engineering Lead (AI)

Location: San Francisco, California, USA; hybrid workplace with significant customer travel

Salary: $200,000–$250,000 USD per year, plus equity and possible variable compensation

Company

Datadog provides an observability platform and is expanding its Forward Deployed Engineering function for startup customers.

What you will do

• Evolve the FDE operating model from engagement intake and scoping through sprint delivery, account-team handoff, success metrics, and reporting.
• Build a catalog of observability quickstarts, custom integrations, AI and LLM observability accelerators, CI/CD instrumentation, and cost-optimization offerings.
• Translate deployment-discovered product gaps into prioritized briefs and strengthen the field-feedback channel with Product Management and Engineering.
• Hire, onboard, manage, and develop full-time FDEs and rotating SWE and TSE secondments.
• Identify recurring customer needs and convert them into reusable integrations, dashboards, automation scripts, and open-source tooling.
• Partner with Sales, Solutions Engineering, Customer Success, and Business Development on account selection, executive reviews, and complex deployments.

Requirements

• 8+ years of experience in forward deployed engineering, solutions architecture, software engineering, or related technical fields, including 3+ years in customer-facing technical roles.
• 2+ years of engineering management or technical leadership experience, including hiring, coaching, performance management, and cross-functional collaboration.
• Experience scaling a technical program, practice, or new function within a high-growth technology company and influencing product roadmaps through field feedback.
• Deep familiarity with Kubernetes, AWS, GCP or Azure, microservices, CI/CD pipelines, infrastructure-as-code, and observability, monitoring, APM, or logging platforms.
• Strong communication with engineering leaders, CTOs, and VP-level executives, plus commercial awareness of ARR, churn risk, and expansion.
• Must be able to work in a hybrid setup in San Francisco and be comfortable with significant travel for customer engagements.

Nice to have

• Datadog platform experience.
• Entrepreneurial mindset and experience navigating matrixed organizations without direct authority.

Culture & Benefits

• Opportunity to shape and scale a strategic function with influence over its operating model and future direction.
• Direct collaboration with Engineering, Product, Sales, Customer Success, and Business Development leadership.
• Exposure to cloud infrastructure, platform engineering, AI observability, deployment strategy, and executive planning.
• Healthcare, dental, parental planning, mental health benefits, and a 401(k) plan with company match.
• Paid time off, fitness reimbursements, and a discounted employee stock purchase plan.