Principal Product Manager, Protection Programs

The Principal Product Manager will own the strategy, development, and performance of a portfolio of protection programs designed to reduce financial risk and build customer confidence throughout the vacation rental reservation experience. The portfolio includes offerings such as damage protection, travel insurance, and chargeback insurance, combining customer experience, commercial performance, and operational risk management. You will shape the product roadmap while developing sustainable business models in partnership with commercial teams and external providers. The role spans the entire customer journey, from coverage discovery and purchase to servicing, cancellation, and claims. Working closely with Design, Engineering, Finance, Legal, Operations, and partner teams, you will turn complex requirements into simple, reliable customer experiences. This is a senior strategic opportunity to identify new growth opportunities, optimize program economics, and build scalable products that deliver measurable value for customers and the business.

• Product Management Experience: At least 10 years of product management experience, including 0-to-1 product development and ownership of strategy and delivery for complex products or product areas.

• Commercial and Business Model Expertise: Strong commercial judgment and experience owning or materially influencing a product's business model, including revenue, margin or contribution, pricing, adoption, partner economics, and cost-to-serve.

• Strategic Execution: Demonstrated ability to turn ambiguous opportunities into focused strategies, business cases, roadmaps, and measurable business outcomes.

• Relevant Product Experience: Experience building products involving financial risk, insurance, payments, lending, warranties, fraud, disputes, or other regulated or partner-dependent services. Direct insurance experience is an advantage.

• Go-to-Market Knowledge: Ability to connect product strategy with execution across customer segmentation, positioning, packaging, distribution, and sales or channel enablement.

• Customer Discovery: Strong customer research and discovery skills, with the ability to balance customer needs against business viability, risk controls, partner requirements, and operational realities.

• Cross-Functional Leadership: Experience working closely with external partners and internal teams across Commercial, Finance, Legal, Compliance, Operations, Support, Design, and Engineering.

• Data-Driven Decision-Making: Ability to use product and financial data to define success metrics, evaluate program performance, understand unit economics, and make evidence-based investment decisions.

• Risk and Operational Judgment: Sound judgment when balancing short-term performance with long-term customer trust, clear coverage expectations, and scalable program operations.

• Technical Collaboration: Comfort working closely with Engineering on technical tradeoffs, system constraints, integrations, and delivery sequencing.

• Communication and Influence: Strong communication skills and the ability to align senior stakeholders and cross-functional teams around strategic decisions and measurable outcomes.

• AI Builder Mindset: Practical experience or interest in using AI tools, LLMs, and agents to prototype solutions, test hypotheses, and address customer needs, with the ability to collaborate with Engineering on production implementation.

• Industry Experience: Experience in insurance, fintech, travel, e-commerce, property technology, vacation rentals, or other consumer or B2B2C businesses is preferred.