Director, Travel Product Merchandising & Portfolio Strategy

Job Summary:

The Director, Travel Product Merchandising & Portfolio Strategy owns how Kensington's travel product comes to life across every touchpoint — the storytelling, the structure, and the strategy behind how it's merchandised. A strategic partner role: this person defines content strategy by line of business, leads category management, and drives the seasonal and specialty merchandising calendar, while managing the team that executes day to day.

Works closely with Travel Product on planning and launches, Sales on building a sellable portfolio, and Marketing on channel alignment. Decisions are grounded in data — booking and performance trends, competitive intelligence, customer feedback — with the goal of product that's not just accurate, but compelling and built to convert. Best suited to someone who thinks in assortment and conversion, not just copy.

Key Responsibilities:

• Own product storytelling and content strategy by line of business — the point of view, structure, and narrative behind every itinerary, service, and destination page.
• Lead category management: assess performance, identify gaps, decide where to invest.
• Drive the seasonal and specialty merchandising calendar end to end.
• Own product accuracy — content and tagging reflect what's actually being sold.
• Partner cross-functionally: Product on planning and launches, Sales on a sellable portfolio, Marketing on channel and campaign alignment.
• Ground merchandising decisions in data — booking and performance trends, competitive intelligence, customer feedback.
• Build the team's fluency with AI-supported workflows without compromising quality.
• Manage, coach, and develop the Merchandising team.

Skills and Qualifications:

• Bachelor's degree.
• 6-8 years in digital merchandising, content strategy, or product marketing, with a track record of strategies that drive growth and profitability.
• 3-5 years managing and developing a team.
• Luxury travel, hospitality, or tourism background strongly preferred.
• Strong financial and analytical skills — able to connect decisions to leads, conversion, close rate, and margin.
• Deep understanding of digital customer journeys: discoverability, storytelling, navigation, search, conversion optimization.
• Genuine curiosity about customer trends and behavior, beyond what the data alone shows.
• Strong editorial judgment — able to set a content point of view and hold others' work to it.
• Practical experience with AI tools in content or merchandising workflows; familiarity with tools like Asana and Cloudinary a plus.
• Proactive and high-ownership — drives strategy forward rather than waiting on direction.
• Strong cross-functional leadership — comfortable in a fast-paced, matrixed environment, able to influence peers and senior stakeholders.

We provide a competitive compensation package with a strong pay for performance rewards approach. Employees have the opportunity to participate in incentive programs and compensation tied to business and individual performance. The expected compensation range for this position is: $110,000 to $130,000.

The actual compensation may vary depending on local market conditions, geography and relevant job-related factors such as knowledge, skills, qualifications, experience, and education/training.

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.

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