Upwork

Principal Software Engineer - AI Native Experiences

Remote

Not SpecifiedCompensation
Expert & Leadership (9+ years)Experience Level
Full TimeJob Type
UnknownVisa
Human Resources, Staffing and Recruiting, Biotechnology, InternetIndustries

Requirements

Candidates should possess over 10 years of hands-on software engineering experience with deep expertise in full-stack development using technologies like React, React Native, and Node.js. A proven track record of leading product experiences that integrate AI or automation, such as LLMs, embeddings, agents, and personalization, is essential. The ideal candidate will be a systems thinker with strong architectural instincts, capable of influencing across teams and product surfaces, and possess a product-first mindset that prioritizes user value, rapid iteration, and shipping with excellence. Experience mentoring engineers and driving alignment through clear, principled technical thinking is also required, along with familiarity with prompt engineering, large-scale experimentation, or building intuitive AI-integrated UX patterns.

Responsibilities

The Principal Software Engineer will lead the design and development of AI-native product experiences across Upwork’s web and mobile platforms. This involves building and delivering AI-native features using technologies like React, React Native, and Node.js. Key responsibilities include defining and evangelizing scalable, safe architectural patterns for AI integration, partnering with cross-functional teams to prototype, validate, and launch tools such as agents, copilots, and recommendation systems. The role also entails delivering trustworthy, performant, and maintainable AI features grounded in customer value and explainability, driving technical direction across multiple teams, providing mentorship, and elevating engineering quality and architectural clarity. Additionally, the engineer will lead complex, cross-functional initiatives from inception through delivery, resolving ambiguity and aligning stakeholders, while shaping strategic product direction by integrating technical insights, experimentation learnings, and innovation opportunities.

Skills

AI
Machine Learning
React
React Native
Node.js
System Design
Architecture
Product Development
Prototyping
Validation
Agents
Copilots
Recommendation Systems

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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