Principal Product Manager – AI Travel

🕒 March 20

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Hopper

WebsiteLinkedInAll Job Openings

201 - 500 employees

💰 $96M Venture Round on 2022-11

Travel • Technology

Hopper is a travel booking platform that offers a one-stop solution for planning trips, including flights, hotels, rental cars, and homes. The platform features advanced options such as price prediction, disruption assistance, and the Price Freeze™ feature, allowing travelers to secure deals and manage changes conveniently. Hopper is known for its mobile app availability on iOS and Android, providing a streamlined experience for its users. It serves millions of travelers worldwide, offering VIP support and various affiliate programs for partners.

📋 Description

• Own the end-to-end strategy and roadmap for pricing intelligence, supplier performance intelligence, and financial reconciliation across all travel verticals. • Architect and evolve reference pricing systems leveraging predictive modeling, elasticity signals, competitive benchmarking, and real-time anomaly detection. • Build the supplier intelligence layer, transforming transactional data into automated performance signals, demand insights, and pricing diagnostics. • Establish and govern the canonical source of truth for revenue, margin, take rate, transactions, and cancellations across systems and partners. • Design model evaluation, monitoring, and feedback frameworks, including drift detection and continuous improvement mechanisms. • Implement automated reconciliation and anomaly detection systems to proactively surface financial inconsistencies at scale. • Drive cross-functional execution across Engineering, Data Science, Finance, Commercial, and Supply to deliver production-grade, model-integrated infrastructure.

🎯 Requirements

• 5+ years of Product Management experience, including ownership of AI-native products and model-driven systems in production. • Hands-on experience writing prompts, designing evaluation harnesses, or prototyping with LLMs/foundation models as part of their PM workflow. • Demonstrated experience operating as an AI-native PM, with hands-on ownership of model lifecycle management including problem framing, signal design, evaluation metrics (e.g., precision/recall tradeoffs, forecasting accuracy), monitoring frameworks, drift detection, and retraining strategies. • Experience shipping predictive systems, anomaly detection platforms, automated decisioning infrastructure, or model-driven pricing systems at scale. • Strong fluency with SQL and large-scale transactional datasets. • Experience owning pricing systems, financial reporting platforms, marketplace intelligence tools, or reconciliation frameworks. • Deep understanding of marketplace economics, revenue mechanics, and pricing strategy. • Track record of delivering complex, cross-functional systems with measurable business impact. • Exceptional communicator able to operate effectively across technical, financial, and commercial stakeholders.

🏖️ Benefits

• Hopper covers 100% of the premiums for group insurance plan. • Hopper offers life, short term and long term disability coverage. • HSA that covers eligible medical and dental expenses. • All employees and dependents have access to Dialogue’s telemedicine services, anytime, anywhere. • All employees have access to an RRSP plan with automatic pre-tax withdrawals per pay. • Please ask us about our very generous parental leave, much above industry standards! • Unlimited PTO. • Carrot Cash travel stipend. • Access to co-working space on demand through FlexDesk AND Work-from-home stipend. • Entrepreneurial culture where pushing limits and taking risks is everyday business. • Open communication with management and company leadership. • Small, dynamic teams = massive impact.