Forward Deployed Engineering Lead

What You’ll Do

• Evolve and scale the FDE operating model end to end: engagement intake, scoping, sprint delivery, handoff back to account teams, and the success metrics (time-to-value, adoption lift, ARR influence, NPS) and reporting infrastructure that support them.
• Build out a catalog of FDE offerings spanning observability quickstarts, custom integration development, LLM/AI observability accelerators, CI/CD pipeline instrumentation, and cost optimization deep dives, and contribute to their pricing and business models, including free-to-paid conversion plays, paid deployment packages, and post-deployment success motions.
• Capture product and feature gaps uncovered during deployments, translate them into structured prioritized briefs, and partner with PM and Engineering to strengthen the field-feedback channel that informs roadmap decisions on a regular cadence.
• Hire, onboard, and develop full-time FDEs, manage a rotating cohort of SWE and TSE secondments, build technical assessment frameworks suited to the customer-embedded nature of the role, and coach the team on engagement, scoping, stakeholder communication, and Datadog platform depth.
• Identify high-value mini-product opportunities (integrations, dashboards, automation scripts, open-source tooling), drive lightweight engineering sprints that convert recurring customer needs into reusable assets, and maintain a prioritized build backlog informed by deployment learnings and competitive intelligence.
• Partner with Sales, Solutions Engineering, Customer Success, and Business Development to identify which accounts enter the FDE motion, represent the function in QBRs and executive business reviews, and serve as a trusted advisor through complex deployment cycles.

Who You Are

• 8+ years of experience in forward deployed engineering, solutions architecture, software engineering, or related technical fields, including at least 3 years in a customer-facing technical role.
• 2+ years of engineering management or technical leadership experience, including hiring, coaching, performance management, and cross-functional collaboration.
• Contributed to or scaled a technical program, practice, or new function within a high-growth technology company, with a track record of influencing product roadmaps through structured field feedback.
• Deep familiarity with modern cloud-native stacks (Kubernetes, AWS/GCP/Azure, microservices, CI/CD pipelines, infrastructure-as-code) and hands-on experience with observability, monitoring, APM, or logging platforms; Datadog experience is a strong plus.
• Communicate exceptionally across audiences from engineering leads and CTOs to VP-level executives, bring strong commercial instinct for how technical decisions translate to ARR, churn risk, and expansion, navigate large matrixed organizations without direct authority, and are comfortable with significant travel to embed with customers.
• Entrepreneurial mindset, thrive in evolving environments, demonstrate strong business acumen, navigate matrixed organizations without direct authority, and are willing to travel to support customer engagements.