Senior Director of Engineering, Developer Enablement

Company: Upwork ($UPWK)

Employment Type: [Not Specified] Location Type: [Not Specified] Salary: [Not Specified]

Position Overview

Upwork is the world’s largest work marketplace, connecting businesses with highly skilled professionals worldwide. From entrepreneurs to Fortune 100 enterprises, companies trust Upwork’s platform to access expert talent, leverage AI-powered work solutions, and drive meaningful business outcomes. Upwork’s AI-powered platform has facilitated over $20 billion in economic opportunity for professionals worldwide. With professionals spanning 10,000+ skills, including AI and machine learning, software development, sales and marketing, customer support, finance and accounting, and more, Upwork empowers businesses of all sizes to scale, innovate, and build agile teams.

We are seeking a Senior Director of Engineering, Developer Enablement to lead the strategy, execution, and delivery of a modern developer platform that accelerates productivity, fosters autonomy, and powers innovation at scale across Upwork. This leader will own the engineering vision and technical execution of key enablement areas including CI/CD systems, developer portals, service frameworks, API platforms, and support for AI/ML infrastructure.

You’ll lead a high-impact team of engineers and managers responsible for shaping our cloud-native developer experience, ensuring that our tools, services, and workflows are fast, intuitive, and scalable. This role requires a strong engineering mindset, technical depth in platform architecture, and a passion for building systems that increase developer joy and efficiency.

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.

What it takes to catch our eye

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

Company Information

Upwork is the world’s largest work marketplace, connecting businesses with highly skilled professionals worldwide. From entrepreneurs to Fortune 100 enterprises, companies trust Upwork’s platform to access expert talent, leverage AI-powered work solutions, and drive meaningful business outcomes. Upwork’s AI-powered platform has facilitated over $20 billion in economic opportunity for professionals worldwide. With professionals spanning 10,000+ skills, including AI and machine learning, software development, sales and marketing, customer support, finance and accounting, and more, Upwork empowers businesses of all sizes to scale, innovate, and build agile teams.

Application Instructions

[Not Specified]