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.
As an UltraLuxe Destination Expert, you will be responsible for the planning, selling, and execution of highly customized, complex journeys for discerning Ultra High Net Worth Individuals (UHNWIs) and luxury travellers.
You will act as a trusted travel advisor, using your destination expertise and knowledge of the luxury travel landscape to create exceptional, highly personalized itineraries. From the initial conversation through the completion of the journey, you will own the client relationship and every detail of the planning process, working closely with our global network of luxury partners and DMCs to bring each journey to life.
This is a high-touch, fast-paced role that requires exceptional attention to detail, responsiveness, commercial acumen, and the ability to anticipate the needs of sophisticated travellers.
Please note this position requires after-hours support for UltraLuxe clients when needed.
Key Responsibilities Building strong, long-term relationships with UltraLuxe clients and luxury travel partners
Consistently delivering highly personalized, seamless journeys
Growing a strong portfolio of UltraLuxe business through recent and repeat clients
Developing deep expertise within your assigned destinations and the broader luxury travel landscape
Becoming a trusted resource for clients, advisors, and internal teams
Identifying opportunities to elevate the client experience and continuously improving how we deliver UltraLuxe travel
Who You Are: A Luxury Travel Expert – You have extensive first hand travel experience and a deep understanding of luxury travel, ideally having lived, worked, or travelled extensively within your area of expertise.



You understand what distinguishes a truly exceptional experience from a luxury product that simply checks the boxes.
A Trusted Advisor – You know how to build credibility quickly with discerning clients, understand their preferences and motivations, and confidently guide them toward the right travel experiences.
A Bespoke Trip Designer – You thrive on creating highly customized, complex itineraries. You are energized by the details and enjoy finding the right combination of destinations, properties, experiences, and partners to create something truly personal.
A Strong Communicator & Storyteller – You can translate your destination knowledge into compelling recommendations and inspire clients through thoughtful conversations and polished written communication.
A Commercially Driven Professional – You understand how to turn opportunities into sales while maintaining the consultative, relationship-driven approach expected of an UltraLuxe advisor. You are comfortable managing the full sales cycle, from initial inquiry through to close and post-sale relationship building.
Highly Responsive & Detail-Oriented – You understand that UltraLuxe clients expect speed, precision, and proactive service. You anticipate needs, stay ahead of details, and take ownership of resolving issues quickly and effectively.
A Relationship Builder – You enjoy developing strong relationships with clients, luxury travel advisors, hotels, DMCs, and other specialty partners. You understand the importance of building a strong network and leveraging it to deliver exceptional journeys.
A Collaborative Team Player – You work closely with colleagues and partners, sharing knowledge and supporting the team while maintaining a high degree of individual ownership over your clients.
A Curious Learner – You are constantly looking for what is new and exceptional in the luxury travel space and enjoy continually expanding your destination and product knowledge.




Qualifications Proven experience in luxury or high-end travel, preferably working with UHNW or highly discerning clientele
Strong destination knowledge and extensive firsthand travel experience
Proven success in consultative sales and relationship management
Demonstrated ability to design and sell highly customized, complex FIT itineraries
Experience managing the full client journey from initial consultation through trip completion
Strong understanding of luxury hotels, DMCs, private experiences, and specialty suppliers
Exceptional attention to detail and organizational skills
Ability to manage multiple complex itineraries and priorities in a fast-paced environment
Strong written and verbal communication skills
Ability to build trust and establish credibility with discerning clients and luxury travel partners
Proven ability to problem-solve independently and remain composed under pressure
Strong commercial mindset with a track record of achieving sales results
Willingness and ability to provide after-hours client support when required
Ability to work collaboratively while taking full ownership of individual client relationships
Cultural Fit: Entrepreneurial and commercially minded
Client-first and service-oriented
Comfortable working in a fast-paced, constantly evolving environment
Highly accountable with a strong sense of ownership
Collaborative and team-oriented
Adaptable, resourceful, and solutions-focused
Comfortable working through ambiguity and changing priorities
Committed to building trust and strong relationships with both clients and colleagues
Preferred Regional Expertise We are particularly interested in candidates with expertise in:
North America
Latin America
Asia
Candidates with expertise in other key UltraLuxe destinations will also be considered.
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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📌 UltraLuxe Destination Expert (Ontario)
🏢 KENSINGTON
📍 Ontario