Travel Counsellor jobs in Toronto, ON

This opening is for an opportunity starting in September 2026. For local applicants, 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

You are a salesperson with experience hitting targets, managing a pipeline of inbound leads, quickly building rapport, and confidently close on high-ticket products. Now you get to do that with an exciting product clients genuinely dream about, a private-guided luxury tour, and crafted entirely around them. No cold calling, only dealing with inbound leads.

As an sales consultant, internally referred to as Destination Expert, you will convert in-bound enquiries into confirmed, high-value bookings. Leads arrive through our website, phone, travel agent partners, referrals, and repeat clients - your job is to qualify, consult, design, close and post-sales account management.

No travel industry background is required; we invest four weeks training every new specialist on our destinations, product, proprietary CRM platform, and sales process. What you bring is the desire to learn our systems and processes, the ability to build trust quickly, ask the right questions, guide clients confidently toward a decision on a meaningful purchase, with a genuine excitement for the product and destinations.

What You’ll Do:

• Manage and convert a pipeline of inbound leads from phone, web, referral, and travel agent channels
• Conduct discovery conversations to understand client travel goals, preferences, and budgets
• Present tailored itinerary proposals and guide clients through a consultative buying journey
• Follow up proactively and manage your pipeline to consistently meet monthly revenue targets
• Work towards a structured ramp-up to $100,000 in monthly gross sales within your first eight months, and sustain that performance thereafter
• Build long-term relationships that generate repeat business and referrals from satisfied clients

What You Bring:

• 2+ years in a sales role with a demonstrable track record of meeting or exceeding revenue targets
• Experience handling inbound leads and managing an active sales pipeline through post sales account management.
• Strong consultative selling skills - you listen deeply, uncover needs, and tailor your approach accordingly
• Comfort selling high-consideration, high-ticket products or services - luxury goods, financial services, real estate, premium hospitality, or similar experience is an asset
• Quickly learning new technology and systems; our proprietary CRM is central to how the team manages and closes business
• Excellent communication skills - confident on the phone and clear and compelling in writing
• Self-motivation and organization

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 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.