--- title: 'Destination Expert - North America at Kensington' canonical: 'https://feeny.ai/job/destination-expert-north-america-kensington-canada-arsvyjah5qh5' type: 'job' last_seen: '2026-10-14' --- # Destination Expert - North America at Kensington - **Company:** Kensington - **Location:** Canada - **Posted:** 2026-10-14 - **Last confirmed live:** 2026-10-14 - **Apply:** https://job-boards.greenhouse.io/kensingtontours/jobs/5265275007 ## 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/). This opening is for an opportunity starting in November 2026. For applicants based in the Greater Toronto Area, this is a hybrid position, currently 1-2 days a week onsite. For those outside of a commutable range of our downtown Toronto head office, this is a Work-from-Home opportunity, not a Work-from-Anywhere opportunity. ## About the Role This is not a typical sales role. This position is for travel professionals who sell consultatively, advise with authority, and understand that for discerning travelers, the journey is everything. As a Destination Expert for North America, you will design fully customized travel experiences tailored to each client. You will spend your time getting to know how your clients like to travel, what they value, and what will make their journey truly meaningful - then translate those insights into itineraries built entirely from scratch. Acting as both a trusted advisor and a destination expert, you’ll guide clients with confidence while working closely with in-destination partners (DMCs or GHAs) to bring each experience to life through privately guided, thoughtfully curated travel. You’ll own the relationship end-to-end, from the first conversation through booking and beyond, serving as the primary point of contact throughout their journey. What You’ll Do: - Sell trips to our clients looking to visit North American destinations (US National Parks, Western Canada & the Rockies, Hawaii & Alaska) - Lead strong discovery conversations to understand client needs, what they are looking for and what matters most to them when travelling - Design and present fully customized itineraries that reflect each client’s preferences and expectations (with an average booking value between $25,000 and $30,000) - Present proposals with confidence, using storytelling to bring each journey to life - Proactively manage your pipeline, guiding clients from initial inquiry through to close and beyond with clear ownership and accountability - Navigate objections and provide solutions that reinforce trust and drive commitment - Deliver seamless, high-touch client experience throughout the booking journey, ensuring strong engagement and follow-through - Leverage post-travel engagements to generate repeat business, referrals, and long-term client relationships What You’ll Bring: - 2+ years of consultative sales experience - Experience living in/visiting or traveling to Western Canada & the Rockies, Hawaii, Alaska and the US National Parks - A self-driven approach with strong accountability for your results, including working toward sales targets and KPIs - Strong communication skills with a natural ability to listen, connect, and build trust - A genuine passion for travel, with curiosity and interest in destinations and cultural experiences - High attention to detail and strong organization skills to manage multiple client journeys at once - Previous experience in luxury travel, luxury sales or high-ticket sales is a strong asset Why Kensington? - An annual salary of $45,000 with an uncapped commission program. The expected compensation range in year one for this position is between $45,000 to $75,000 - 3 weeks paid vacation plus paid sick time - Extended health and dental benefits - RRSP / 401(k) matching - 4-week structured onboarding covering our destinations, product portfolio, sales process, and proprietary CRM system - FAM trips to experience our destinations and the Kensington product firsthand - IATA card for personal travel discounts and industry access - Ongoing mentorship and coaching within a company that actively promotes from within We provide a competitive compensation package with a strong pay-for-performance rewards approach.  For this position, we anticipate offering an annual salary of $45,000 with the opportunity to participate in a commission program tied to achievable targets and individual performance.  The expected compensation range for this position is: $45,000 to $75,000. The actual compensation may vary depending on local market conditions, and relevant job-related factors such as knowledge, skills, qualifications, experience, and education/training. 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) ## Other roles at Kensington - [Intern - Sales Strategy & Analytics](https://feeny.ai/job/intern-sales-strategy-analytics-kensington-toronto-1x8pj8m6g5c1) — Toronto, Canada - [Intern - Sales Support](https://feeny.ai/job/intern-sales-support-kensington-toronto-wka6g9w8mp6b) — Toronto, Canada - [Private Client Manager](https://feeny.ai/job/private-client-manager-kensington-united-states-nyvrjs8a322h) — United States - [Director, Integrated Marketing](https://feeny.ai/job/director-integrated-marketing-kensington-toronto-z8yv626xcmd3) — Toronto, Canada - [UltraLuxe Destination Expert](https://feeny.ai/job/ultraluxe-destination-expert-kensington-canada-3fj547qzmmd0) — Canada - [Director, Sales – Outside Sales, Midwest](https://feeny.ai/job/director-sales-outside-sales-midwest-kensington-columbus-7yg7yyf5bsfy) — Columbus, OH - [UltraLuxe Destination Expert](https://feeny.ai/job/ultraluxe-destination-expert-kensington-united-states-mfzpnepqgdkf) — United States - [Private Client Manager](https://feeny.ai/job/private-client-manager-kensington-canada-t5h4q8ykbbt3) — Canada - [Talent Acquisition Specialist (Tech & Corp Recruitment)](https://feeny.ai/job/talent-acquisition-specialist-tech-corp-recruitment-kensington-toronto-rjmtrt80gh1m) — Toronto, Canada - [Marketing Insights & Reporting Analyst](https://feeny.ai/job/marketing-insights-reporting-analyst-kensington-toronto-9tndw8dybamm) — Toronto, Canada