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Principal Product Manager - AI Travel (100% Remote - Canada)

Hopper Inc.

Job Overview

Location

Toronto - Remote

Job Type

Full-time

Full Job Description

📋 Description

• As a Principal Product Manager for AI Travel at Hopper Inc., you will own the intelligence and reconciliation backbone of Hopper Technology Solutions (HTS), shaping the financial truth and pricing integrity across Flights, Hotels, Cars, and Ancillaries for millions of travel transactions. This role is foundational to Hopper’s mission of bringing transparency, flexibility, and savings to travelers globally by ensuring model-driven systems are accurate, adaptive, and trusted.
• You will own the end-to-end strategy and roadmap for pricing intelligence, supplier performance intelligence, and financial reconciliation across all travel verticals, architecting reference pricing systems using predictive modeling, elasticity signals, competitive benchmarking, and real-time anomaly detection to drive partner economics and supplier transparency.
• You will build the supplier intelligence layer by transforming transactional data into automated performance signals, demand insights, and pricing diagnostics, while establishing and governing the canonical source of truth for revenue, margin, take rate, transactions, and cancellations across systems and partners.
• You will design and implement model evaluation, monitoring, and feedback frameworks—including drift detection and continuous improvement mechanisms—and lead automated reconciliation and anomaly detection systems to proactively surface financial inconsistencies at scale.
• You will drive cross-functional execution across Engineering, Data Science, Finance, Commercial, and Supply teams to deliver production-grade, model-integrated infrastructure, ensuring AI systems are measurable, reliable, and aligned with business outcomes.
• You will partner deeply with Data Science and Engineering to productionize predictive models, define evaluation frameworks, manage model lifecycles, and ensure intelligence systems are not only accurate but also interpretable and actionable for stakeholders.
• You will operate as an AI-native Product Manager with hands-on experience in prompt engineering, LLM prototyping, and evaluation harnesses, applying these skills directly in your workflow rather than overseeing others.
• You will contribute to Hopper’s rapid growth as a leading global travel fintech and commerce platform, helping power B2B partnerships with industry leaders like Capital One, Air Canada, Nubank, and Uber through HTS, which represents over 75% of the business.
• You will work in a high-impact, entrepreneurial environment where pushing limits and taking risks is everyday business, enabling you to make massive impact despite small, dynamic teams.

🎯 Requirements

• 5+ years of Product Management experience with ownership of AI-native products and model-driven systems in production, where AI is foundational to product behavior—not merely an additive feature.
• Hands-on experience writing prompts, designing evaluation harnesses, or prototyping with LLMs/foundation models as part of your PM workflow, not just overseeing others doing it.
• Demonstrated experience in end-to-end model lifecycle management, including problem framing, signal design, evaluation metrics (e.g., precision/recall, 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, with proven ability to derive insights from complex travel commerce data.
• Experience owning pricing systems, financial reporting platforms, marketplace intelligence tools, or reconciliation frameworks in high-volume transaction environments.
• Deep understanding of marketplace economics, revenue mechanics, and pricing strategy, with a track record of delivering complex, cross-functional systems with measurable business impact.
• Exceptional communication skills to operate effectively across technical, financial, and commercial stakeholders, translating technical concepts into business value.

🏖️ Benefits

• Hopper covers 100% of the premiums for group insurance plans, including life, short-term, and long-term disability coverage.
• Access to an HSA that covers eligible medical and dental expenses, plus Dialogue’s telemedicine services for employees and dependents, available anytime, anywhere.
• RRSP plan with automatic pre-tax withdrawals per pay, generous parental leave (above industry standards), unlimited PTO, and a Carrot Cash travel stipend.
• Access to co-working space on demand via FlexDesk and a work-from-home stipend, supporting flexible, productive remote work.
• Entrepreneurial culture with open communication with leadership, small dynamic teams, and massive impact opportunities in a proven, well-funded startup with pre-IPO equity upside.

Skills & Technologies

Product Management

Senior

Remote

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Hopper Inc.

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About Hopper Inc.

Hopper is a travel technology company that uses predictive analytics and machine learning to forecast flight and hotel prices, allowing consumers to book travel at optimal times. Founded in 2007 and headquartered in Montréal, Canada, it operates mobile-first booking platforms and provides fintech products like price freeze, cancel-for-any-reason, and rebooking guarantees to reduce travel risk.

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