AI Product Lead (Principal Product Manager)

Accountabilities:

As the product owner for an AI-driven insurance marketplace, you will define the product vision, guide technical decisions, and ensure AI agents can interact with the platform effectively and reliably. Your responsibilities will include:

• Define and own the product roadmap, balancing AI agent needs, technical architecture, and broader business objectives.

• Own the agent-facing product experience, including data exchanged with AI agents, recommendations, reasoning, integration capabilities, and trust signals.

• Lead product testing and quality assurance by developing and maintaining evaluation datasets, identifying potential failure modes, and defining measurable standards for successful agent interactions.

• Monitor agent performance using metrics such as task completion, accuracy, response speed, and successful follow-through after handoffs.

• Build rapid prototypes of agent workflows and test them with real or simulated agents to validate assumptions before committing significant engineering resources.

• Translate insights from agent behavior and experimentation into improvements to data models, exposed reasoning, product functionality, and system architecture.

• Partner with AI technical leadership and engineering teams to evaluate architectural trade-offs, optimize cost and performance, and balance the needs of consumers with those of calling agents.

• Develop relationships with AI platforms to understand how their agents discover, select, and interact with external services, using these insights to inform product design.

• Help communicate the product mission, experiments, and findings through open collaboration and publication.

• Provide leadership with clear, regular updates on progress, emerging insights, product risks, and strategic decisions.

• Define requirements for complex technical systems and ensure product execution remains aligned with the overall vision.

• Drive continuous improvement through data analysis, structured experimentation, and disciplined product delivery.

Requirements:

The ideal candidate is an experienced product leader with a proven record of shipping AI products, strong technical judgment, and the ability to turn ambiguous problems into successful products. Required qualifications and relevant experience include:

• At least 8 years of experience in product management, engineering, or a closely related field at a technology company, including senior ownership of a product area.

• Demonstrated experience building and shipping AI-powered products or agent-based systems into production, ideally within an AI lab, AI-native company, or team developing large language model (LLM) products.

• Strong understanding of AI evaluation methods, including how to translate ambiguous goals into measurable tests, identify failure modes, and determine when a product or model should be rolled back.

• Working knowledge of agent architectures, large language models, retrieval, orchestration, guardrails, and the trade-offs between cost, latency, and performance.

• Sufficient technical depth to participate meaningfully in architecture and code reviews, challenge assumptions, and collaborate effectively with engineers.

• Proficiency in SQL for independent data analysis and comfort using Python for lightweight prototyping.

• Strong product judgment and the ability to make progress on loosely defined problems in a fast-changing environment.

• A track record of leading ambitious, complex projects with small teams and delivering measurable outcomes.

• Experience defining requirements for complex technical systems or platforms.

• A data-driven approach to decision-making, combined with strategic thinking and disciplined execution.

• Excellent communication skills, with the ability to explain technical concepts and product decisions to both technical and non-technical stakeholders.

• Strong attention to detail, dependable delivery, collaborative instincts, and a bias toward action.

• Curiosity, resilience, and a commitment to continuous learning as AI capabilities and industry standards evolve.

The following qualifications are advantageous but not required:

• Experience in insurance or financial technology.

• Familiarity with Model Context Protocol (MCP), Agent-to-Agent (A2A) communication, agent registries, or emerging standards for agentic commerce.

• Experience contributing to or publishing within open developer communities.

Benefits:

• Annual base salary of $174,800–$205,700 USD for this full-time remote role.

• Potential participation in variable cash bonus programs, depending on role eligibility.

• Equity compensation, subject to applicable eligibility.

• Comprehensive health, welfare, and well-being benefits, based on role eligibility.

• Remote work arrangement within the United States.

• Opportunity to shape an emerging AI-powered marketplace and influence the future of agentic commerce.

• The chance to lead ambitious product initiatives at the intersection of artificial intelligence, technology platforms, and insurance.