Sr Director of Engineering, Developer Enablement

Upwork ($UPWK) 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.

• 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

• 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-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.

At Upwork, you’ll shape the future of work for a global, remote-first workforce, creating economic opportunities for professionals worldwide. While we have a physical office in Palo Alto, we currently hire full-time employees in 21 U.S. states, making it easier than ever to join our mission from wherever you call home.

Our culture is built on trust, risk-taking, customer focus, and excellence, all in service of our core mission: to create economic opportunities so people have better lives. We embrace authenticity and inclusion, encouraging everyone to bring their whole selves to work. Personal and professional growth is a priority here, supported through development programs, mentorship, and our Upwork Belonging Communities.

We’re proud to offer benefits that go beyond the basics, including comprehensive medical coverage for you and your family, unlimited PTO, a 401(k) plan with matching, 12 weeks of paid parental leave, and an Employee Stock Purchase Plan. Visit our Life at Upwork page to learn more about our values, working principles, and the overall employee experience.

Ready to help shape the future of work? Check out our Careers page and follow us on LinkedIn, Facebook, Instagram, TikTok, and X. to learn more about life at Upwork.

Upwork is an Equal Opportunity Employer committed to recruiting and retaining a diverse and inclusive workforce. We do not discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, or other legally protected characteristics under federal, state, or local law.

Please note that a criminal background check may be required once a conditional job offer is made. Qualified applicants with arrest or conviction records will be considered in accordance with applicable law, including the California Fair Chance Act and local Fair Chance ordinances.