Sr. Product Manager Work Guarantees

About the role

You will lead the strategy and operations for Work Guarantees, a core trust initiative for SMB customers. This role involves managing the entire lifecycle of the program, from eligibility logic and remediation workflows to the AI systems that detect and prevent issues. You will act as a product owner who balances technical infrastructure with business unit economics and legal requirements.

Key facts

What you'll do

• Define the product roadmap and strategy for Work Guarantees, overseeing program design and financial health.
• Develop and maintain AI observability infrastructure for anomaly detection and proactive contract monitoring.
• Convert complex legal and operational needs into user-friendly experiences for SMB clients.
• Collaborate with engineering, data science, finance, legal, and operations to build scalable, defensible programs.
• Use quantitative data and customer feedback to prioritize features and measure business impact.
• Utilize AI tools for research synthesis and pattern analysis while maintaining human oversight of all outputs.
• Operate with founder-level accountability to drive program performance and execution.

Requirements

• Proven history of managing product programs that link design with operational outcomes.
• Experience launching LLM or AI-assisted features in marketplace or consumer products, specifically regarding risk or health signals.
• Strong analytical skills with the ability to manage unit economics alongside finance teams.
• Ability to thrive in ambiguous 0-to-1 environments.
• Demonstrated success in aligning diverse stakeholders like legal, finance, and engineering around complex program goals.

Skills & tools

• AI observability infrastructure
• Unit economics modeling
• Structured prompting for research and documentation
• Cross-functional stakeholder management

Practical notes

This role is initially employed through a partner until the Toronto hub is fully established by Q4 2026. Once the hub opens, the position requires 3 days of in-office work per week. Compensation includes eligibility for an annual bonus or sales incentive plan and long-term equity incentives. Upwork uses BrightHire for interview recording and transcription; candidates may opt out during scheduling. All hiring decisions are made by humans.