Product Manager - Book with AI

We are looking for a Product Manager to shape the future of business travel through Book with AI. You will own the product across Hotels, Rental Cars, and Rail, while serving as the day-to-day product lead for the team and making complex bookings feel as natural, trustworthy, and seamless as working with an expert travel agent. We are looking for a Product Manager to own the Book with AI product end to end across Hotels, Rental Cars, and Rail. Your mission is to make booking complex business travel feel as natural as working with an expert travel agent - while making sure the agent is accurate, policy-aware, transparent, and reliable enough for real transactions. This is a highly cross-functional, hands-on role. You’ll lead day-to-day execution across the entire traveler journey - from the initial request through search, comparison, booking, post-booking support, and recovery when things go wrong, partnering closely with engineering, design, applied AI/ML, data, travel domain experts, operations, and other product teams.  You’ll shape the conversational and user-interface experiences that power Book with AI, helping travelers express their needs, evaluate trade-offs, make confident decisions, and complete bookings with less effort. You’ll stay close to the customer experience by reviewing real conversations, leading bug bashes, interpreting evaluation results, identifying patterns in user feedback, and ensuring the team remains focused on the highest-impact opportunities. The ideal candidate thrives in ambiguity, learns quickly, and is energized by AI-native products. They create clarity and momentum without waiting for perfect information, roll up their sleeves, and drive work through uncertainty and chaos. What You'll Do Own the vision, strategy, roadmap, and execution for Book with AI across Hotels, Rental Cars, and Rail. Own the full Book with AI journey: intent understanding, search, ranking and recommendations, policy and personalization, comparison, contract, checkout, booking, and post-booking support. Define a coherent cross-LOB experience for users who want to plan and book multiple parts of a trip, including clear sequencing, handoffs, and expectations. Improve the product's key outcomes, including successful booking completion, conversion, time to book, user effort, CSAT, trust, and repeat usage. Lead experimentation across conversational flows, recommendations, search and booking surfaces, using clear hypotheses and measurable success criteria. Partner with AI, data, and engineering teams to improve intent understanding, ranking, recommendations, personalization, tool orchestration, and the use of conversational and UI-based experiences. Establish a strong product feedback loop, such as organizing and prioritizing bug bash findings, investigate production conversations, connect issues to root causes, and ensure fixes are validated before and after release. Define meaningful goals and evaluation criteria for AI behavior, including task completion, factual accuracy, policy compliance, correct tool and UI usage, response quality, latency, and safe recovery from failures. Align stakeholders across product, engineering, design, ML, data, travel operations, support, and adjacent Navan teams. Communicate product decisions, tradeoffs, status, risks, and learnings clearly to leadership and the broader organization. Represent the customer in every discussion and ensure that the AI is transparent about limitations, unsupported requests, changing prices, availability, and booking status. What We're Looking For 4+ years of experience in product management, with a track record of owning and shipping customer-facing products. Experience owning a complex product or product area end to end, including strategy, discovery, prioritization, execution, launch, and measurement. Strong product judgment and the ability to balance customer value, business impact, technical complexity, reliability, and speed. Experience improving measurable product outcomes such as conversion, task completion, engagement, retention, or customer satisfaction. Excellent written and verbal communication skills, with the ability to create alignment with leadership, collaborate across diverse stakeholders, and communicate effectively with customers. A data-informed approach to product decisions, combined with strong qualitative judgment and customer empathy. Curiosity about AI products and the ability to reason about probabilistic systems, failure modes, evaluation, guardrails, and human trust. A practical, ownership-oriented mindset: you find the problem, clarify it, bring the right people together, and drive it through resolution. Nice to hav e Experience building AI assistants, conversational products, recommendation systems, search experiences, or agentic workflows. Experience defining or using LLM evaluations, quality rubrics, production monitoring, or experimentation frameworks. How you