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.