Work Guarantees sit at the heart of why SMB customers keep coming back to Upwork. As Senior Product Manager for this program, you will own both the product strategy and the operational machinery that makes these guarantees real: the eligibility logic, remediation workflows, and AI observability infrastructure that detects problems before they become bad experiences. This is full-spectrum ownership, spanning product, operations, and unit economics, for one of Upwork's most consequential customer trust initiatives. You will partner across engineering, legal, data science, finance, and operations to build programs that are defensible, scalable, and genuinely useful to the SMBs who depend on them. Responsibilities: • Own the product strategy and roadmap for Work Guarantees, including program design, eligibility logic, remediation workflows, and the unit economics that keep the program healthy • Build and operate the AI observability infrastructure powering Work Guarantees, including anomaly detection, contract health signals, and proactive intervention surfaces • Translate complex trust, legal, and operational requirements into clean, intuitive experiences for SMB customers who expect Upwork to have their back • Partner closely with engineering, data science, legal, finance, and operations to ship scalable, defensible guarantee programs that hold up under edge cases and volume • Use quantitative analysis and customer insights to drive roadmap prioritization, inform go-to-market decisions, and measure program performance against business outcomes • Apply AI tools and structured prompting to accelerate research synthesis, anomaly pattern analysis, and product documentation, reviewing outputs critically before acting on them • Set direction and move with urgency, operating with a founder's accountability for both what ships and how it performs What It Takes to Catch Our Eye: • Demonstrated ownership of product programs at the intersection of product design and operational outcomes, not just shipping features but holding accountability for the system's end-to-end performance • Experience shipping LLM-based or AI-assisted features in consumer or marketplace products, particularly around risk detection, monitoring, or contract health signals • Strong analytical foundation with the ability to stress-test unit economics alongside finance as fluently as you partner with UX and engineering on what to build • Comfort in 0-to-1, ambiguous environments where the scope is yours to define and the accountability is yours to own • Proven ability to align legal, finance, operations, and engineering stakeholders around a shared program direction, especially when tradeoffs are significant 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 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 and follow us on LinkedIn, Facebook, Instagram, TikTok, and X to learn more about life at Upwork. The annual base salary range for this position is displayed below. The range displayed reflects the minimum and maximum salary for this position, and individual base pay will depend on your skills, qualifications, experience, and location. Additionally, this position is eligible for the annual bonus plan or sales incentive plan and eligibility to participate in our long term equity incentive program. Annual Base Compensation $167,500-$261,500 CAD