Senior Director of Engineering, Developer Enablement

Summary

Join Upwork as a Senior Director of Engineering, Developer Enablement and lead the strategy, execution, and delivery of a modern developer platform. You will own the engineering vision and technical execution of key enablement areas, including CI/CD systems, developer portals, service frameworks, and API platforms. Lead a high-impact team of engineers and managers responsible for shaping our cloud-native developer experience. This role demands a strong engineering mindset, technical depth in platform architecture, and a passion for building systems that enhance developer joy and efficiency. You will define and drive the engineering strategy for Developer Enablement, lead and scale a high-performing engineering organization, and define and track engineering KPIs. The position requires proven engineering leadership experience at scale and a strong technical acumen in platform engineering.

Requirements

• Proven engineering leadership experience at scale, with direct accountability for developer platforms, cloud-native services, and enablement tooling
• Strong technical acumen in platform engineering, including cloud architecture, CI/CD pipelines, and developer workflow optimization
• Experience delivering developer-facing UIs or portals (e.g., Backstage) that enable self-service and reduce friction
• Deep understanding of metrics-driven engineering execution and continuous improvement using DORA or similar benchmarks
• Demonstrated ability to lead through influence, drive cross-functional alignment, and build scalable engineering systems that support diverse teams and modern workloads including AI/ML
• Engineering-productivity analytics — deep grasp of DORA/Flow metrics, SDLC telemetry pipelines, and cost-insight tooling
• API gateway & platform architecture — REST/GraphQL design patterns, schema governance, auth & rate-limiting
• Quality engineering & shift-left testing — automated unit/integration/perf/security test frameworks, chaos & synthetic testing practices
• Cloud-native & micro-services — Kubernetes operations, service-mesh patterns, and migration strategies for decomposing monoliths
• Developer-experience enablement — Backstage service catalog, local/remote dev-env tooling, inner-loop automation

Responsibilities

• Define and drive the engineering strategy for Developer Enablement, including internal platforms, developer tooling, and self-service infrastructure
• Lead and scale a high-performing engineering organization, fostering a culture of ownership, innovation, and execution excellence
• Define and track engineering KPIs that surface in org-wide dashboards and guide investment decisions
• Architect, secure, and operate the API platform—including gateway policies, versioning, traffic-splitting, and scalability targets
• Embed comprehensive automated testing into CI/CD pipelines to maintain release velocity without compromising reliability
• Own developer productivity tooling, from environment provisioning to Backstage plugins that cut onboarding and cycle times
• Champion the use of developer productivity and DORA metrics to inform strategy, track impact, and continuously improve
• Foster strong cross-functional relationships with Security, Product, and other Engineering teams to align platform capabilities with business and engineering needs

Preferred Qualifications

Machine-learning principles & agentic AI frameworks (bonus) – hands-on experience designing model pipelines, orchestrating LLM/agent workflows, and integrating ML capabilities into developer platforms

Benefits

• Comprehensive medical coverage for you and your family
• Unlimited PTO
• A 401(k) plan with matching
• 12 weeks of paid parental leave
• An Employee Stock Purchase Plan