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.

Job Description

This is not a typical sales role. This is a call to professionals who sell with elegance, advise with authority, and understand that, for discerning travelers, the journey is everything. Kensington's Cruise Experts are the architects of extraordinary adventures - designing bespoke Land & Sea itineraries that take clients to the far edges of the earth, from the polar ice fields to the Galapagos, from hidden Mediterranean coves to the untouched rivers of Asia. You will not just book travel, you transform it.

From the moment of first contact to welcoming your travelers home, you will guide high-end clientele through a unique and exhilarating portfolio of luxury products and experiences. You will offer an array of premium-to-luxury cruise line products, along with meticulously curated pre- and post-cruise experiences, including private guides, charter flights, luxury lodges, and immersive cultural experiences.

As a Cruise Expert, you will own the full sales cycle with confidence: uncovering each client's vision in the discovery call, navigating vessel selection and cabin categories, coordinating logistics, and closing with conviction. You will action incoming leads and cultivate a book of loyal, high-net-worth clients who return to you again and again because no one else delivers at your level.

Please note: for applicants based in the Greater Toronto Area, this is a hybrid position, currently 1 day per 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.

What You'll Do:

Lead high-touch discovery conversations that reveal what moves your clients - then design journeys that exceed those expectations.
Craft seamless Land & Sea itineraries that combine bespoke fly-cruise options, luxury lodges, private guides, and multi-country extensions.
Manage availability, quotes, and bookings with precision, working with our curated network of world-class cruise partners.
Build and deepen a portfolio of loyal, high-net-worth clients through exceptional service, proactive communication, and a consultative sales approach that prioritizes the client experience first.
Bring destinations to life through vivid storytelling and passion.
Consistently meet and exceed monthly revenue targets while elevating the client experience.

What You Bring:

3+ years of consultative cruise or luxury travel sales experience.
First-hand experience with luxury and/or expedition cruising
Demonstrated ability to design and sell complex Land & Sea itineraries, and FIT travel for high-net-worth clientele.
A track record of exceeding sales targets while delivering a high-touch client experience.
Strong organizational discipline to manage multiple active itineraries simultaneously without missing details.
Calm and creative problem-solving instincts to find solutions before clients notice the problem existed.
Fluency with systems and technology, from CRMs to booking platforms and supplier systems.
Strong written and verbal communication - polished, warm, and precise in all client interactions.

What’s In It for You?

Competitive base salary + uncapped commission structure
3 weeks paid time off
Comprehensive benefits package
Performance-based FAM trips
Industry discounts
Extensive training and onboarding program
Strong opportunities for growth and career progression

Cultural Fit

Thrives working in a technology and KPI driven organization.
Able to thrive in an entrepreneurial environment.
Highly functional in a fast-paced, constantly changing workplace - building plans through iterations from learning what’s working and not working.
Ability to build trust and work through conflict both upwards and downwards.

#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.

Kensington

Cruise Expert

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Kensington

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