Sr. Product Manager Work Guarantees

Upwork Inc.'s (Nasdaq: UPWK) family of companies connects businesses with global, AI-enabled talent across every contingent work type including freelance, fractional, and payrolled. This portfolio includes the Upwork Marketplace, which connects businesses with on-demand access to highly skilled talent across the globe, and Lifted, which provides a purpose-built solution for enterprise organizations to source, contract, manage, and pay talent across the full spectrum of contingent work. From Fortune 100 enterprises to entrepreneurs, businesses rely on Upwork Inc. to find and hire expert talent, leverage AI-powered work solutions, and drive business transformation. With access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, the Upwork family of companies enables businesses of all sizes to scale, innovate, and transform their workforces for the age of AI and beyond.

Since its founding, Upwork Inc. has facilitated more than $30 billion in total transactions and services as it fulfills its purpose to create economic opportunities so people have better lives. Learn more about the Upwork Marketplace at Upwork.com and follow us on LinkedIn, Facebook, Instagram, TikTok, and X; and learn more about Lifted at Go-Lifted and follow on LinkedIn.

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

Upwork is establishing an operational hub in Toronto, Canada. The new office is expected to be fully operational by Q4 2026. This role will require 3 days in office once we have an office open.

This position will initially be employed through a partner to ensure a seamless hiring process while we establish the hub. Once the hub is established, there may be opportunities to transition to employment with Upwork, depending on business needs and other requirements. While employed by the partner, you'll work as part of Upwork's team, with access to our resources, culture, and growth opportunities.

Our partner will offer competitive benefits. When Upwork's hub is established, we will be excited to offer employment and benefits directly as business needs require.

Upwork is committed to building a diverse, inclusive, and equitable workforce. Employment decisions are made without regard to race, color, religion, gender, sexual orientation, gender identity, national origin, disability, or any other status protected by applicable law.

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To learn more about how Upwork processes and protects your personal information as part of the application process, please review our Global Job Applicant Privacy Notice