This opening is for an opportunity starting in November 2026 or January 2027. 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 perks 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.
This is a full-time position. Current hours of operation are 8:30 am to 8:00 pm EST. Weekend coverage, Late Shifts, and Statutory Holidays are shared on a rotating basis among the team.
This is a commission sales role with a base salary of $45,000, health and wellness benefits, three weeks of vacation, and additional incentives for top performers.

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📌 Destination Expert (Ontario)
🏢 Range Group - Job Postings
📍 Ontario