UltraLuxe Destination Expert in Winnipeg

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 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 UltraLuxe 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.
• 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.
• 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.
• Highly Responsive & Detail-Oriented – You understand that UltraLuxe clients expect speed, precision, and proactive service.
• A Relationship Builder – You enjoy developing strong relationships with clients, luxury travel advisors, hotels, DMCs, and other specialty partners.
• 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

• North America
• Africa & Middle East
• Latin America
• Asia
• Europe North (Scandinavia)

Candidates with expertise in other key UltraLuxe destinations will also be considered.