Principal Product Manager, Protection Programs

Accountabilities: Product Vision and Strategy: Define and own the vision, strategy, and roadmap for Protection Programs, connecting customer value, risk reduction, and sustainable business performance. Customer and Market Understanding: Develop a deep understanding of homeowners, guests, internal teams, and insurance or protection partners to identify meaningful customer needs across the reservation lifecycle. Portfolio Strategy: Develop and manage a portfolio of offerings, including damage protection, travel insurance, and chargeback insurance, determining where to invest, expand, refine, or retire programs. Commercial Model Ownership: Partner with Commercial, Finance, and external providers to develop and optimize program economics, evaluating pricing, conversion, coverage, partner economics, claims costs, and operational expenses to improve sustainable contribution. Growth and Business Cases: Identify and validate opportunities across customer segments, distribution moments, packaging, pricing, and partner capabilities. Translate opportunities into clear business cases and measurable product initiatives. End-to-End Customer Experience: Improve the protection journey from discovery and selection through purchase, servicing, cancellation, and claims, ensuring coverage terms, eligibility requirements, and customer expectations are clear. Go-to-Market Strategy: Collaborate with Commercial and go-to-market teams on positioning, packaging, channel strategy, and enablement to ensure programs are compelling, accurately represented, and easy to adopt. Operational Reliability and Compliance: Work with Operations, Claims, Support, Legal, Compliance, and external partners to establish reliable, scalable program rules and service processes that meet applicable requirements. Performance Measurement: Use customer research and data to monitor awareness, attachment and adoption, conversion, retention, loss and claims trends, customer satisfaction, and unit economics. Adjust priorities based on performance and emerging evidence. Cross-Functional Delivery: Lead initiatives from discovery and business case development through definition, delivery, launch, and iteration, aligning teams on outcomes, dependencies, and decisions. Strategic Decision-Making: Balance customer experience, commercial returns, risk exposure, and operational complexity, communicating tradeoffs and recommendations to senior stakeholders. Customer Advocacy: Represent customer needs and the overall health of the Protection Programs portfolio in product decisions, helping teams develop a shared understanding of program performance and customer value. AI-Enabled Product Development: Use AI tools, large language models, and agents to rapidly prototype solutions and validate hypotheses, partnering with Engineering to turn proven concepts into scalable production capabilities. Requirements 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. Benefits Competitive Salary: Annual salary range of $170,000–$205,000 USD, based on relevant experience. Annual Bonus: Eligibility for a variable annual bonus based on company and individual performance. Equity: Company equity. Retirement Savings: 401(k) plan with a 4% employer match that vests immediately. Healthcare: Comprehensive medical, dental, and vision coverage, including 100% employer-paid dental and vision premiums for individual coverage and a low-cost medical plan option. Mental Health: 10 free mental health visits. Family Support: 16–18 weeks of paid parental leave for birthing parents and 10 weeks for non-birthing parents, plus infertility coverage. Time Off: Generous paid time off, return-to-office (RTO) benefits for full-time exempt employees, sick leave, holidays, and a personal holiday. Pet Insurance: Access to pet insurance. Travel Benefits: Annual travel credit after one year of employment and discounts on stays at participating properties. Learning and Development: Structured onboarding, learning resources, and professional development opportunities. Employee Communities: Employee Resource Groups that support connection and celebrate diverse communities. Remote Work: Remote opportunities across eligible US locations. Candidates must reside in an approved location by their first day of employment.