---
title: 'Director, Travel Product Merchandising & Portfolio Strategy at Kensington'
canonical: 'https://feeny.ai/job/director-travel-product-merchandising-portfolio-strategy-kensington-toronto-pxps964k08cc'
type: 'job'
last_seen: '2026-09-16'
---

# Director, Travel Product Merchandising & Portfolio Strategy at Kensington

- **Company:** Kensington
- **Location:** Toronto, Canada
- **Posted:** 2026-08-28
- **Last confirmed live:** 2026-09-16
- **Apply:** https://job-boards.greenhouse.io/kensingtontours/jobs/5221562007

## Job description

Kensington delivers the world’s most personal travel experiences. We bring to life each client’s desire to travel in a way that’s tailored specifically for them, in the company of local private guides who ensure that they enjoy the authentic best of their destination. The result is a unique journey rich in memories that last a lifetime!

We achieve this because of our extraordinary people, passionate experts with deep knowledge of their destinations. They are what enables us to deliver remarkable experiences in over 120 countries worldwide, and across each of our businesses – Private Touring, Cruises, Villas, Yachts, Expeditions, Ultraluxe Land, Private Jets, and Air.

To learn more about Kensington, visit [kensingtontours.com](http://kensingtontours.com/).

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.

#LI-Remote The Range Group may use artificial intelligence throughout the recruitment process to screen, assess or select applicants for this position. These tools assist our hiring team but do not replace human judgment. Final hiring decisions are ultimately made by the hiring team.

We thank all candidates for their interest, however, only those selected for an interview will be contacted.

## About Kensington

## Company Overview
- **One-liner**: Kensington delivers the world’s most personal, private-guided luxury travel experiences across more than 120 countries, designing tailor-made journeys for discerning clients.
- **Entity Type**: Private (Privately Held)
- **Headquarters**: Toronto, Ontario, Canada
- **Founded**: Year not publicly available
- **Founders**: Names not publicly available

## Core Business
- **Primary industry**: Luxury Travel Arrangements / Custom Tour Operations
- **Target customers**: B2C (high-net-worth individuals and luxury travelers seeking personalized, private-guided experiences)
- **Mission or purpose statement**: To bring to life each client’s desire to travel in a way that’s tailored specifically for them, in the company of local private guides who ensure they enjoy the authentic best of their destination — creating a unique journey rich in memories that last a lifetime.

## Products & Services
- **Private Guided Tours (Kensington Tours)**: Custom, private-guided itineraries in over 100 countries, crafted by destination experts with deep in-country knowledge.
- **Kensington Cruises**: Curated cruise experiences with private guides and personalized shore excursions.
- **Kensington Yachts**: Luxury yacht charters with bespoke itineraries.
- **Kensington Villas**: High-end villa rentals with concierge-level service.
- **Kensington Expeditions**: Adventure-focused private expeditions to remote destinations.
- **Kensington Corporate**: Tailored corporate travel and incentive programs.
- **Kensington Jets**: Private jet travel arrangements.
- **Kensington Air**: Air travel booking and logistics services.

## Market Standing
- **Valuation/Market Cap**: Not disclosed (privately held)
- **Key Metric**: Annual Revenue of **$27.0M** (latest available data)
- **Notable Investors/Partners**: Not publicly disclosed. The company operates under the TripArc umbrella (a travel technology and services group).
- **Growth Signals**:
  - Headcount of **541 employees** (+22.3% year-over-year, adding 132 people)
  - LinkedIn followers: **32,980** (up 27.6% year-over-year)
  - Operates in **13 countries** (including Canada, US, UK, Ireland, Egypt, Kenya, Saudi Arabia, Mexico, Spain, New Zealand)
  - Named one of “The Best Adventure Travel Companies on Earth” by National Geographic Adventure Magazine
  - Received “World’s Best Awards” from Travel + Leisure Magazine (2011, 2015)

## Competitive Advantages
- **Deep local expertise**: Employs destination experts with genuine in-country knowledge, not generic travel agents.
- **Private-guided model**: Every journey is private and guided by local experts — a premium differentiator vs. group tour operators.
- **Global scale with personal touch**: Operates in 120+ countries while maintaining a highly personalized, one-client-at-a-time approach.
- **24/7 on-trip support**: Unbeatable around-the-clock support for travelers in any time zone.
- **Multi-brand portfolio**: Offers tours, cruises, yachts, villas, expeditions, corporate travel, and private jets — a comprehensive luxury travel ecosystem.

## Strategic Focus
- **Technology & data-driven personalization**: Actively hiring for BI Developer, Senior BI Developer (Executive Analytics & Fabric Platform), Manager of Business Insights, and Analyst roles — signaling a push toward data-driven product and customer experience.
- **Commercial expansion**: Hiring a VP of Travel Product & Commercial Strategy, Directors of Sales, and Cruise Experts — indicating growth in sales channels and product lines.
- **Digital platform investment**: Senior Director of Website & Digital Platforms on the leadership team; hiring a Director of CX Optimization & Experimentation.
- **Cybersecurity**: Hiring a Director of Cybersecurity, suggesting scaling of digital infrastructure.

## Why Work Here
- **Culture & values**: Emphasizes five core values: *We Earn Trust*, *We Fail/Learn Fast*, *We Deal in Facts*, *We Are a Team*, and *We Take Ownership*. Highly collaborative, data-driven, and accountability-focused environment.
- **Diversity & inclusion**: **67% of leadership positions held by women**; **35 nationalities** represented on the team.
- **Flexibility**: Offers a **remote work program** and opportunities to work remotely when necessary (though primary HQ is Toronto office-based).
- **Travel perks**: Top performers receive **familiarization trips**; shared love of exploration is a core part of the culture.
- **Wellness & benefits**: Extended health coverage including employee assistance and wellness offerings; lunch-hour yoga classes; regular learning sessions.
- **Compensation**: Industry-leading salaries, **RRSP matching program**, referral bonuses, and recognition rewards.
- **Community impact**: Active volunteer program (Kensington Cares) — supports local charities and global causes.
- **Growth & training**: Committed to career advancement with ongoing training and development opportunities.
- **Team composition**: 1,430 total years of travel industry experience among staff; strong talent pipeline from companies like Travel Edge, Flight Centre, Navigatr, and G Adventures.

## Sources
1. [kensingtontours.com](https://www.kensingtontours.com/careers)
2. [linkedin.com](https://www.linkedin.com/company/kensington-tours)
3. [job-boards.greenhouse.io](https://job-boards.greenhouse.io/kensingtontours/jobs/5047598007)
4. [cbinsights.com](https://www.cbinsights.com/company/kensington-tours)
5. [builtin.com](https://builtin.com/company/kensington-tours)

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