Principal Software Engineer - AI Native Experiences

Upwork ($UPWK) is the world’s human and AI-powered work marketplace that connects businesses with highly skilled, AI-enabled independent talent from across the globe. From entrepreneurs to Fortune 100 enterprises, companies rely on Upwork’s trusted platform and its mindful AI companion, Uma, to find and hire expert talent, leverage AI-powered work solutions, and drive business transformation. With on-demand access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, Upwork enables businesses of all sizes to scale, innovate, and build agile teams for the age of AI and beyond.

Upwork’s platform has facilitated more than $25 billion in economic opportunity for talent around the world. Learn more at Upwork.com and follow us on LinkedIn, Facebook, Instagram, TikTok, and X.

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

This is a role for a seasoned product builder who thrives in ambiguity, scales through systems, and leads by doing. You’ll work closely with Product, Design, and our Umami (AI/ML) team to translate cutting-edge models into meaningful user experiences—all while maintaining a focus on architecture, iteration speed, and customer impact.

• Build and deliver AI-native features across Upwork’s web and mobile platforms using technologies like React, React Native, and Node.js.
• Define and evangelize scalable, safe architectural patterns for AI integration across customer-facing experiences.
• Partner with cross-functional teams to prototype, validate, and launch tools like agents, copilots, and recommendation systems.
• Deliver trustworthy, performant, and maintainable AI features grounded in customer value and explainability.
• Drive technical direction across multiple teams, providing mentorship and elevating engineering quality and architectural clarity.
• Lead complex, cross-functional initiatives from inception through delivery, resolving ambiguity and aligning stakeholders.
• Shape strategic product direction by integrating technical insights, experimentation learnings, and innovation opportunities.

• 10+ years of hands-on software engineering experience with deep expertise in full-stack development (React, React Native, Node.js).
• Proven track record leading product experiences that integrate AI or automation (LLMs, embeddings, agents, personalization).
• Systems thinker with strong architectural instincts and the ability to influence across teams and product surfaces.
• A product-first mindset—you prioritize user value, move fast, and ship with excellence.
• Experience mentoring engineers and driving alignment through clear, principled technical thinking.
• Familiarity with prompt engineering, experimentation at scale, or building intuitive AI-integrated UX patterns.

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 34 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 to learn more about opportunities 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.