Job Description: AI Solutions Operator

Company Overview

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.

Position Overview

We’re looking for a high-agency operator to solve real business problems with AI. Think: “How do we turn our scattered knowledge base into a single AI-native source of truth that answers 90% of team & user questions instantly?” You’ll go from problem → solution hypothesis → vendor/tool → prototype → rollout, fast.

This role is not about writing research papers or waiting for engineering handoffs. You’ll go from idea to solution hypothesis to prototype to rollout, talking to vendors, shipping scrappy versions, running PoCs, validating ROI, and building internal playbooks for scale. You are obsessed with automation, AI-native tools, and the practical application of frontier technology. If you’re excited about turning business pain points into scalable AI solutions—without waiting on a roadmap—this role is for you.

Responsibilities

• Reframe vague problems into sharp, testable hypotheses suitable for AI-native solutions.
• Conduct discovery and requirements gathering with internal stakeholders to inform solution design.
• Research & evaluate AI tools, platforms, and vendors through hands-on testing and proof-of-concept pilots.
• Build and iterate on scrappy internal prototypes using no-code platforms, LLM APIs, and automation tools (think: days, not months). Implement tools with minimal/no engineering effort.
• Define success metrics and validate ROI for solutions before scaling across teams or functions.
• Develop rollout plans, documentation, and internal playbooks to ensure adoption and repeatability.

What it takes to catch our eye

• Proven ability to ship internal tools or solutions in a fast-paced, resource-constrained environment.
• Hands-on experience with AI/LLM technologies, agents, no-code platforms, APIs, and product discovery methods.
• Strong product sense and comfort operating in ambiguity with minimal direction.
• A track record of independently driving cross-functional initiatives from idea to adoption.
• Curiosity, scrappiness, and a bias toward action when exploring new technologies.
• Startup or venture studio mindset: own the problem, ship fast.

Company Culture & Benefits

Come change how the world works. 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.