Datadog for Startups - Forward Deployed Engineering Lead

Datadog's Forward Deployed Engineering function is in an active growth phase, and the FDE Lead will play a central role in shaping what comes next. Working in close partnership with the Head of Datadog for Startups and Forward Deployed Engineers, and the existing FDE team, you will help define and expand the FDE framework, build out the structures and processes that allow the team to operate at scale, and extend the program's reach well beyond any single customer segment. This role sits at the rare intersection of sales, execution, program design, and hands-on engineering leadership. You are part field technical leader, part program architect, and part cross-functional connector. You will help determine what the FDE motion looks like at Datadog, contribute to its playbook, and push the boundaries of what the team can deliver. At Datadog, we place value in our office culture - the relationships and collaboration it builds, and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. 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. - Help drive lightweight engineering sprints to convert recurring customer needs into reusable assets that scale across the FDE portfolio. - 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: - Have 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. - Have 2+ years of engineering management or technical leadership experience, including hiring, coaching, performance management, and cross-functional collaboration. - Have 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. - Bring 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. Datadog values people from all walks of life. We know not everyone will meet all the above qualifications on day one. That’s okay. If you’re passionate about technology and want to grow your experience, we encourage you to apply. Benefits and Growth: - Shape and scale a rapidly growing strategic function with significant influence on its operating model and future direction. - Partner directly with leadership across Engineering, Product, Sales, Customer Success, and Business Development. - Influence customer outcomes while helping inform Datad

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. Strong communication across engineering leads to VP-level executives, commercial instinct for how technical decisions translate to ARR, churn risk, and expansion; comfortable navigating large matrixed organizations and willing to travel to embed with customers. Entrepreneurial mindset and ability to thrive in evolving environments, with strong business acumen and willingness to travel.

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. Help drive lightweight engineering sprints to convert recurring customer needs into reusable assets that scale across the FDE portfolio. 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.