Principal Software Engineer, AI Native Experiences

Upwork is seeking a Principal Engineer to lead the design and development of AI-native product experiences across our web and mobile applications. In this hands-on role, you’ll drive end-to-end delivery of intelligent, assistive, and adaptive features that reimagine how work gets done on the world’s leading work marketplace.

You’ll partner closely with product, design, and AI/ML teams to translate cutting-edge models into valuable product capabilities—and you’ll do it while maintaining a strong focus on clean architecture, customer experience, and speed of iteration.

This is a role for an experienced product builder who thrives in ambiguity, scales through systems, and leads by doing.

Responsibilities

• Build end-to-end AI-native product features across Upwork’s web and mobile platforms using technologies like React, React Native, and Node.js.
   

• Define technical strategies and architectural patterns that make AI integration consistent, safe, and scalable across customer-facing experiences.
   

• Collaborate with Product, Design, and Umami (AI/ML) teams to prototype, validate, and launch intelligent tools, agents, copilots, and recommendation systems.
   

• Demonstrated experience shipping customer-facing features involving AI or automation (LLMs, agents, embeddings, personalization, etc.).
   

• Design for trust, performance, and maintainability—building AI features that are fast, explainable, and grounded in customer value.
   

• Mentor engineers and act as a multiplier, raising the technical bar and driving architectural clarity across multiple teams or product domains.
   

• Own the delivery of complex, cross-functional product features, resolving ambiguity and coordinating execution across functions.
   

• Shape strategic decisions by integrating technical vision, product outcomes, and innovation opportunities

• Familiarity with prompt engineering, experimentation at scale, or building AI-integrated UX patterns.

What It Takes to Catch Our Eye

• 10+ years of hands-on software engineering experience, with deep expertise in full-stack product development (React, React Native, Node.js, etc.).
   

• Strong systems thinking and architectural instincts; you’ve led initiatives that shaped the direction of product experiences across multiple surfaces or teams.

• Product-first mindset with an ability to navigate ambiguity, iterate quickly, and deliver with urgency and quality.
   

• Strong communication skills; you drive alignment through clear technical thinking, not just consensus.
   

• Experience mentoring engineers and influencing at the org level