Destination Expert

Range Group - Job Postings; Toronto; Hybrid; CAD 45,000 - 75,000; Full time

Benefits offered by this job

Uncapped commission

3 weeks paid time off

Medical & dental benefits

Retirement matching program

Job summary

Kensington in Toronto is seeking an experienced travel sales professional for a hybrid role starting in November 2026 or January 2027. You will guide high-end clients from discovery to post-travel follow-up, designing bespoke itineraries and guiding complex bookings with care and precision.

This is not a transactional role; it rewards storytelling, loyalty, and deep client relationships. Expect uncapped commissions, a strong base, and opportunities for destination certifications.

Qualifications

• 2+ years in consultative sales with luxury or high-ticket clients.
• Proven ability to close complex sales and exceed revenue targets.
• Strong travel knowledge and destination expertise.

Responsibilities

• Lead discovery conversations to understand travel goals and preferences.
• Design bespoke itineraries with in-destination teams.
• Present proposals and build excitement for Kensington's offerings.
• Guide clients through the booking process with seamless communication.
• Act as trusted travel advisor before, during, and after journeys.
• Follow up post-travel to gather feedback and drive referrals.

Skills

Consultative sales

Luxury travel

Attention to detail

Emotional intelligence

Job description

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 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.

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.