Sr Director of Engineering, Developer Enablement

Remote

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Not SpecifiedCompensation

Expert & Leadership (9+ years)Experience Level

Full TimeJob Type

UnknownVisa

Online Marketplaces, Biotechnology, Software DevelopmentIndustries

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, deep understanding of metrics-driven engineering execution using DORA or similar benchmarks, and demonstrated ability to lead through influence and drive cross-functional alignment. Familiarity with API gateway and platform architecture, quality engineering, shift-left testing, cloud-native principles, and microservices is required. Machine-learning principles and agentic AI frameworks are a bonus.

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.

Skills

Developer Enablement

CI/CD

Developer Portals

Service Frameworks

API Platforms

AI/ML Infrastructure

Cloud-Native

Platform Architecture

Engineering Strategy

Engineering Leadership

Technical Execution

Scalability

Security

Upwork

Online platform connecting freelancers and clients

About Upwork

Upwork connects freelancers with clients looking for various services in the gig economy, which focuses on short-term contracts instead of permanent jobs. The platform allows freelancers to create profiles that showcase their skills, while clients can post job listings for specific projects. Freelancers bid on these projects, and clients choose the best candidates based on proposals and reviews. Upwork earns revenue through service fees charged to freelancers based on their earnings, with a tiered structure that rewards long-term client relationships. The platform also offers premium memberships and additional services for enhanced visibility and access to job listings. Upwork provides tools for time tracking, invoicing, and project management, making it easier for both freelancers and clients to manage their work and payments. The goal of Upwork is to facilitate successful project completion by bridging the gap between freelancers and clients.

San Francisco, CaliforniaHeadquarters

2015Year Founded

$143.8MTotal Funding

IPOCompany Stage

Consulting, Enterprise SoftwareIndustries

10,001+Employees

Benefits

Health Insurance

Unlimited Paid Time Off

401(k) Retirement Plan

401(k) Company Match

Parental Leave

Employee Stock Purchase Plan

Risks

Increased competition from Fiverr and Toptal threatens Upwork's market share.

The new Fiverr-style Project Catalog may commoditize services, reducing freelancers' perceived value.

Strategic shifts under new management may not align with current client expectations.

Differentiation

Upwork connects freelancers with clients across diverse industries, enhancing global work opportunities.

The platform offers tools like time tracking and invoicing for efficient project management.

Upwork's tiered fee structure incentivizes long-term client relationships, differentiating it from competitors.

Upsides

Upwork's acquisition of Objective AI enhances its AI capabilities for better talent matching.

The introduction of Featured Jobs increases visibility for job posts, attracting more candidates.

Upwork's recognition as the top job posting site boosts its credibility among employers.

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