Experienced Destination Expert
- Pay
- $45,000 – $75,000 per year
- Location
- United States · Hybrid
- Job type
- Full-time
- Level
- Mid-level
- Experience
- 2+ years
- Listed
- 31 days ago
Skills & highlights for this role
- consultative sales
- luxury travel
- client relationship management
Also useful
- high-ticket sales
- CRM
Stated benefits & perks
- Extended health
- Dental
- 401k match
About the role
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.
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
Why Kensington?
- 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.
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.
From Kensington's careers page, first listed on Rolev.ai on October 10, 2026. Rolev.ai is not the employer.
How Rolev.ai helps with this application
Rolev.ai is a job search and application tool for US job seekers. For this Experienced Destination Expert role at Kensington, it shows how your resume fits, tailors your resume to the posting, and prepares the application for you to review.
See how you fit
Openings from employer career sites are ranked against your whole resume—and searchable inside Claude, ChatGPT, and Cursor via Rolev.ai MCP.
Tailor without inventing
Every change to your resume is checked against your original. New experience goes in only with your yes—zero fabricated claims.
Draft the full kit
Tailored and Full Match resumes, role-specific cover letters, and answers to employer screening questions are prepared in seconds.
1-Click Extension Autofill
The Chrome extension fills the employer's Greenhouse, Workday, Lever, or Ashby form in 1 click. You review it and press Submit.
Common questions
What is the salary for the Experienced Destination Expert role at Kensington?
The Experienced Destination Expert posting at Kensington states compensation of $45,000 – $75,000 per year. It is listed as a full-time position. Final pay may depend on location, experience, and interview evaluation on Kensington's official career site.
Where is the Experienced Destination Expert job at Kensington located?
This Experienced Destination Expert position at Kensington is located in United States (Hybrid). Always check Kensington's application page for specific state eligibility or relocation policies.
What qualifications are required for Experienced Destination Expert at Kensington?
For the Experienced Destination Expert role, Kensington highlights 2+ years of relevant experience; experience with consultative sales, luxury travel, client relationship management. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.
How do I apply for the Experienced Destination Expert position at Kensington?
This listing links directly to Kensington's Greenhouse application page. You can apply directly on Kensington's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Greenhouse application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.