Job Summary: The Director of Product & Content owns the product and content strategy that brings Kensington Vacations' portfolio to life across every touchpoint — the storytelling, the structure, and the strategy behind how it's built, planned, and merchandised. A strategic partner role: this person sets product and content direction by line of business, shapes how product is planned and launched.

Works closely with Procurement and Technology on planning, launches, and the AI tools used to build itineraries and content at scale; with Sales on building a sellable portfolio; and with 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 product, 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.
• Guide category management in partnership with the Merchandising Specialist: supports direction on performance, gaps, and where to invest.
• Own product accuracy — content and tagging reflect what's actually being sold.
• Partner cross-functionally: Product and Technology on planning, launches, and tooling; Sales on a sellable portfolio; Marketing on channel and campaign alignment.
• Ground product development decisions in data — booking and performance trends, competitive intelligence, customer feedback.
• Work hands-on with AI tools to accelerate itinerary creation, product content, and merchandising workflows, and build the team's fluency with AI-supported workflows without compromising quality.
• Manage, coach, and develop the team.

Skills and Qualifications:

• Bachelor's degree.
• 6-8 years in product management, content strategy, or product marketing, with a track record of strategies that drive growth and profitability.
• 3-5 years managing and developing a team.
• 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.
• Hands-on experience using AI tools for itinerary creation, content generation, or product workflows — comfortable evaluating and adopting new AI platforms, not just using existing ones; familiarity with tools like Asana and Cloudinary a plus.
• Merchandising expertise is an asset
• 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 base compensation range for this position is: $100,000 to $120,000.

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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