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 .
About The Role As an Ultra Luxe 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 Ultra Luxe clients when needed.
Key Responsibilities Building strong, long-term relationships with Ultra Luxe clients and luxury travel partners
Consistently delivering highly personalized,



seamless journeys
Growing a strong portfolio of Ultra Luxe business through new 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 Ultra Luxe travel
Qualifications 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 Ultra Luxe 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 Ultra Luxe 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 solid 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 Cooperative 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
Excep

📌 Ultraluxe destination expert (Winnipeg)
🏢 KENSINGTON
📍 Winnipeg