Staff Product Manager, Transactions & Trust

Accountabilities: Own the strategy and product direction for the complete transaction lifecycle, including checkout, payments, payouts, fees, insurance, credits, and dispute resolution across web and mobile experiences. Develop and continuously refine the product strategy based on customer insights, business evidence, operational realities, and measurable outcomes. Lead decisions around insurance products and programs, including regional coverage, verification, pricing, and international considerations. Design fee structures that are flexible for the business while providing clear, transparent explanations to guests and operators before and after payment. Own product experiences and policies related to trip changes, cancellations, credits, refunds, disputes, and other situations where expectations between marketplace participants differ. Lead the transition toward a unified review and reputation system so customer reputation can carry consistently across the combined platform. Define and manage outcomes such as checkout conversion, payment success, payout accuracy and timing, dispute rates, and the proportion of transactions retained on-platform. Make complex product tradeoffs involving customer protection, operator fairness, transparency, conversion, policy flexibility, and predictable revenue. Influence Finance, Operations, Customer Support, Insurance, and other Product teams through clear reasoning, shared objectives, and strong cross-functional relationships. Conduct ongoing customer discovery by speaking directly with guests and operators, reviewing support cases, participating in dispute reviews, and identifying the operational impact of product decisions. Frame problems before defining solutions, establish system entities, states, constraints, and money flows, and contribute to event-storming sessions and technical/product documentation. Define measurable signals before launches and monitor outcomes after release, identifying when initiatives should be expanded, changed, or discontinued based on evidence. Help the team ship focused, reversible improvements quickly through guarded rollouts, reliable reconciliation, and disciplined execution. Mentor other Product Managers, contribute to hiring decisions, and improve product-development practices across the organization. Work closely with a dedicated designer and a fully resourced product team while serving as the dedicated Product Manager for the relevant product area. Requirements Demonstrated experience owning product strategy for checkout, payments, or payouts within a two-sided marketplace or comparable transaction-driven environment. Proven ability to author product strategy and set direction rather than simply execute an existing roadmap. Track record of delivering ambitious, measurable objectives that span multiple teams and functions. Experience navigating high-stakes decisions involving legal, finance, external partners, senior leadership, or other stakeholders with competing priorities. Demonstrated experience designing pricing or fee experiences that improve transparency while considering conversion, revenue, and customer trust. Experience treating policies such as cancellation, refund, credit, or dispute rules as product experiences that can be designed, tested, measured, and improved. Strong systems-thinking capabilities, with the ability to understand entities, states, constraints, dependencies, and financial flows within complex products. Strong analytical and data-driven decision-making skills, including the ability to independently investigate product performance and customer behavior. Excellent customer-discovery skills and willingness to regularly engage directly with customers and operational teams. Strong cross-functional leadership and influencing skills, with the ability to create alignment without relying on organizational authority. Demonstrated ability to make difficult product tradeoffs and communicate decisions clearly. Experience mentoring Product Managers, contributing to hiring, or improving product-team processes. Strong written and verbal communication skills and the ability to translate complex systems and decisions into clear product direction. Relevant academic credentials are welcome but not required; demonstrated experience delivering and measuring successful products is prioritized. Experience with insurance products, embedded insurance, or coverage verification is a plus. Experience with payment processors, marketplace payouts, or split-payment systems is a plus. Experience building configurable fee or pricing systems is a plus. Familiarity with chargebacks, disputes, review and reputation systems, or transaction operations is a plus. Experience migrating live transactions between platforms while protecting in-progress bookings is a plus. Marketplace experience in travel, rentals, local services, or similar transaction-heavy industries is a plus. Familiarity with international or multi-region transaction, insurance, or payment considerations is a plus. Benefits Fully remote position within the United States. High overlap with U.S. Eastern Time working hours. Direct reporting relationship to the Chief Product Officer. Dedicated Product Manager ownership within a fully resourced product team. Dedicated designer partnership. Opportunity to own a company-level product strategy spanning payments, payouts, insurance, fees, disputes, and trust. Significant cross-functional influence across Product, Finance, Operations, Support, and external partners. Fast-moving product environment focused on measurable outcomes and continuous discovery. Opportunity to mentor other Product Managers and influence hiring and product-development practices. Relevant degrees are welcome but not required, with demonstrated product impact and shipped work prioritized. Opportunity to work on complex marketplace challenges involving financial systems, trust, pricing, policy, and customer experience. The source job description does not specify a salary range or additional benefits.