VP, Travel Product & Commercial Strategy

We are currently looking for a VP, Product to lead the Kensington Product function at a critical point of transformation — evolving from a traditional, manually-driven product model to a scaled, technology-enabled product engine that directly drives growth. You will own the end-to-end product strategy, with a mandate to build a system that scales high-quality, differentiated travel experiences globally.

• Build and operationalize a model to rapidly expand itinerary volume and breadth across destinations, themes, and search demand
• Translate product frameworks (themes, destinations, traveler intent) into system-driven outputs and improve speed-to-market

• Unlock high-impact growth opportunities, and ensure execution of travel product strategy that influences lead generation, conversion, revenue and margin
• Partner closely with Procurement and Revenue teams to ensure price competitiveness and margin discipline

• Define and enforce quality standards and brand positioning across all travel itineraries
• Own product logic within internal systems (e.g. supplier prioritization, ranking, exclusions)

• Serve as a senior external representative of Kensington Product across key industry forums, trade shows, and partner engagements
• Maintain a deep understanding of global travel trends and translate market insights into actionable strategy

• Direct experience in the travel industry is a must
• 10–15+ years experience in Travel Product, Merchandising, or Category leadership
• Proven track record in scaling product and assortment, driving commercial outcomes
• Thrive in fast-paced, fast-growth environments
• Strong commercial acumen with previous success in breaking down complex problems and translating strategy into execution
• A strategic thinker with tech-enabled mindset
• Excellent people leadership skills
• Low ego, high ownership and comfortable with ambiguity

We are committed to providing employment accommodation in accordance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act. If you require accommodation due to a disability at any stage of our hiring process, please advise us when completing your application.