Destination Expert

This opening is for an opportunity starting in November 2026. For local applicants, this is a hybrid position, currently 1 day a week onsite. For those outside of a commutable range of our office located in downtown Toronto, this is a Work-from-Home opportunity, not a Work-from-Anywhere opportunity.

About the Role

We’re looking for an experienced professional with a passion for travel and strong sales acumen. In this full-cycle consultative sales role, you will guide prospective clients from the first discovery call to post-travel follow-up - turning interest into commitment, and bookings into lifelong relationships. 

This is not a transactional or call center role. It’s about high-touch engagement, thoughtful storytelling, and a deep understanding of how to personalize every client journey with care and precision.

What You’ll Do:

• Lead in-depth discovery conversations to understand each client’s travel goals, style, and preferences
• Design bespoke itineraries in collaboration with our in-destination teams
• Present proposals with confidence, use storytelling to build excitement for clarity in Kensington's unique offerings
• Guide clients through the booking process and provide seamless communication throughout
• Act as a trusted travel advisor before, during, and after client journeys
• Follow up post-travel to gather feedback, drive referrals, and foster loyalty

What You’ll Need:

• 2+ years of consultative sales experience, ideally with luxury or high-ticket clients
• Proven ability to close complex sales cycles and exceed revenue targets
• Deep passion for travel and strong destination knowledge with a desire to help others explore the world
• Polished, articulate communicator with emotional intelligence and active listening skills
• Strong organization and high attention to detail to manage multiple journeys simultaneously
• A self-motivated and performance-driven approach without resorting to hard selling
• Comfortable in a dynamic, fast-paced, collaborative environment
• Experience in luxury travel or hospitality is an asset

Why Kensington?

• A competitive compensation package with uncapped commission earnings, 3-weeks paid time off, and after probation, medical & dental benefits program, and the ability to participate in a retirement matching program.
• Represent a globally recognized premium brand with exceptional product offerings
• Work with warm, qualified leads - no cold calling!
• Earn competitive base compensation + uncapped commission and luxury travel perks
• Gain access to world-class training and destination certifications
• Collaborate with a passionate, supportive, and travel-obsessed team
• Grow with a company that values ambition, creativity, and expertise

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.

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.