Sr. Product Manager Work Guarantees

Upwork•Toronto, ON

6d•CA$167,500 - CA$261,500•Remote

About The Position

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.

Requirements

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

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