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

Hands-on experience writing prompts, designing evaluation harnesses, or prototyping with LLMs/foundation models as part of their PM workflow (not just overseeing others doing it)

, 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.

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.

We are seeking an exceptional, AI-native Senior+ Product Manager to build and lead the intelligence and reconciliation backbone of HTS across Flights, Hotels, Cars, and Ancillaries.

This role owns the systems that define pricing intelligence, supplier performance reporting, and financial truth across millions of travel transactions.

You will design and scale model-driven infrastructure that continuously interprets transactional data, generates reference pricing, detects performance shifts, reconciles financial flows, and governs revenue integrity in real time.

This is a foundational role at the intersection of marketplace economics, machine learning, and financial systems.

You will partner deeply with Data Science and Engineering to productionize predictive models, define evaluation frameworks, manage model lifecycles, and ensure intelligence systems are measurable, adaptive, and trusted.

The work you do will directly shape partner economics, supplier transparency, and HTS’s global commerce platform.

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.