Experienced Destination Expert

This opening is for an opportunity starting in October 2026. For applicants based in the Greater Toronto Area, this is a hybrid position, currently 1-2 days a 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.

About the Role 

This is not a typical sales role. This position is for travel professionals who sell consultatively, advise with authority, and understand that for discerning travelers, the journey is everything.

As a Luxury Travel Advisor (internally known as 'Destination Expert'), you will design fully customized travel experiences tailored to each client. You will spend your time getting to know how your clients like to travel, what they value, and what will make their journey truly meaningful - then translate those insights into itineraries built entirely from scratch.

Acting as both a trusted advisor and a destination expert, you’ll guide clients with confidence while working closely with in-destination partners (DMCs or GHAs) to bring each experience to life through privately guided, thoughtfully curated travel. You’ll own the relationship end-to-end, from the first conversation through booking and beyond, serving as the primary point of contact throughout their journey.

What You’ll Do:

• Lead strong discovery conversations to understand client needs, what they are looking for and what matters most to them when travelling
• Design and present fully customized itineraries that reflect each client’s preferences and expectations (with an average booking value between $25,000 and $30,000)
• Present proposals with confidence, using storytelling to bring each journey to life
• Proactively manage your pipeline, guiding clients from initial inquiry through to close and beyond with clear ownership and accountability
• Navigate objections and provide solutions that reinforce trust and drive commitment
• Deliver seamless, high-touch client experience throughout the booking journey, ensuring strong engagement and follow-through
• Leverage post-travel engagements to generate repeat business, referrals, and long-term client relationships

What You’ll Bring:

• 2+ years of consultative sales experience
• A self-driven approach with strong accountability for your results, including working toward sales targets and KPIs
• Strong communication skills with a natural ability to listen, connect, and build trust
• A genuine passion for travel, with curiosity and interest in destinations and cultural experiences
• High attention to detail and strong organization skills to manage multiple client journeys at once
• Previous experience in luxury travel, luxury sales or high-ticket sales is a strong asset

• An annual salary of $45,000 with an uncapped commission program. The expected compensation range in year one for this position is between $45,000 to $75,000
• 3 weeks paid vacation plus paid sick time
• Extended health and dental benefits
• RRSP / 401(k) matching
• 4-week structured onboarding covering our destinations, product portfolio, sales process, and proprietary CRM system
• FAM trips to experience our destinations and the Kensington product firsthand
• IATA card for personal travel discounts and industry access
• Ongoing mentorship and coaching within a company that actively promotes from within

#LI-Remote

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.