---
title: 'Director, Sales – Outside Sales, Midwest at Kensington'
canonical: 'https://feeny.ai/job/director-sales-outside-sales-midwest-kensington-united-states-eh3shg3h62r4'
type: 'job'
last_seen: '2026-09-09'
---

# Director, Sales – Outside Sales, Midwest at Kensington

- **Company:** Kensington
- **Location:** United States
- **Posted:** 2026-05-15
- **Last confirmed live:** 2026-09-09
- **Apply:** https://job-boards.greenhouse.io/kensingtontours/jobs/5139041007

## Job description

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](http://kensingtontours.com/).

## The Role

We are looking for a sales-driven Director of Sales with a proven track record as an experienced and gifted Sales Representative. Ideal candidate should have a successful, stable work history, and you’re now keen to explore new ground. This role is most suitable for in those who are comfortable working from a home office and will focus on top-producing luxury leisure travel agencies and agents within the territory.    (Midwest based in MI, OH, IN, IL)

## Key Accountabilities

- Identify and develop sales from top leisure agencies within your territory
- Setting appointments and calling on key accounts to engage owners/managers and their agent teams in a professional and compelling manner
- Represent Kensington Tours at trade shows and preferred agency network events, presenting our products and services and vigorously following up to ensure traction
- Provide superior levels of customer service and sales support to all agencies within the territory
- Analyze and manage key agencies' sales data to creatively initiate improvement
- Achieving sales revenue targets within budget

## Qualifications

- Highly motivated and enthusiastic with an innate sales drive
- Supplier Rep or retail travel industry experience in this territory is essential
- Familiarity with premium and luxury product lines preferred
- Demonstrate professional and superior sales presentation techniques
- Strategic business planning, analyzing, and reporting
- Strong negotiator
- Advanced skills in interpersonal relationship management
- Valid driver's license, reliable vehicle, and qualify to rent a car.
- Valid passport
- Ability to bend and lift up to 30 lbs.
- Ability to travel within assigned territory on a regular basis, up to 70%.

Additional Information

We offer an attractive remuneration package and a dynamic working environment. 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.

## About Kensington

## Company Overview
- **One-liner**: Kensington delivers the world’s most personal, private-guided luxury travel experiences across more than 120 countries, designing tailor-made journeys for discerning clients.
- **Entity Type**: Private (Privately Held)
- **Headquarters**: Toronto, Ontario, Canada
- **Founded**: Year not publicly available
- **Founders**: Names not publicly available

## Core Business
- **Primary industry**: Luxury Travel Arrangements / Custom Tour Operations
- **Target customers**: B2C (high-net-worth individuals and luxury travelers seeking personalized, private-guided experiences)
- **Mission or purpose statement**: To 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 they enjoy the authentic best of their destination — creating a unique journey rich in memories that last a lifetime.

## Products & Services
- **Private Guided Tours (Kensington Tours)**: Custom, private-guided itineraries in over 100 countries, crafted by destination experts with deep in-country knowledge.
- **Kensington Cruises**: Curated cruise experiences with private guides and personalized shore excursions.
- **Kensington Yachts**: Luxury yacht charters with bespoke itineraries.
- **Kensington Villas**: High-end villa rentals with concierge-level service.
- **Kensington Expeditions**: Adventure-focused private expeditions to remote destinations.
- **Kensington Corporate**: Tailored corporate travel and incentive programs.
- **Kensington Jets**: Private jet travel arrangements.
- **Kensington Air**: Air travel booking and logistics services.

## Market Standing
- **Valuation/Market Cap**: Not disclosed (privately held)
- **Key Metric**: Annual Revenue of **$27.0M** (latest available data)
- **Notable Investors/Partners**: Not publicly disclosed. The company operates under the TripArc umbrella (a travel technology and services group).
- **Growth Signals**:
  - Headcount of **541 employees** (+22.3% year-over-year, adding 132 people)
  - LinkedIn followers: **32,980** (up 27.6% year-over-year)
  - Operates in **13 countries** (including Canada, US, UK, Ireland, Egypt, Kenya, Saudi Arabia, Mexico, Spain, New Zealand)
  - Named one of “The Best Adventure Travel Companies on Earth” by National Geographic Adventure Magazine
  - Received “World’s Best Awards” from Travel + Leisure Magazine (2011, 2015)

## Competitive Advantages
- **Deep local expertise**: Employs destination experts with genuine in-country knowledge, not generic travel agents.
- **Private-guided model**: Every journey is private and guided by local experts — a premium differentiator vs. group tour operators.
- **Global scale with personal touch**: Operates in 120+ countries while maintaining a highly personalized, one-client-at-a-time approach.
- **24/7 on-trip support**: Unbeatable around-the-clock support for travelers in any time zone.
- **Multi-brand portfolio**: Offers tours, cruises, yachts, villas, expeditions, corporate travel, and private jets — a comprehensive luxury travel ecosystem.

## Strategic Focus
- **Technology & data-driven personalization**: Actively hiring for BI Developer, Senior BI Developer (Executive Analytics & Fabric Platform), Manager of Business Insights, and Analyst roles — signaling a push toward data-driven product and customer experience.
- **Commercial expansion**: Hiring a VP of Travel Product & Commercial Strategy, Directors of Sales, and Cruise Experts — indicating growth in sales channels and product lines.
- **Digital platform investment**: Senior Director of Website & Digital Platforms on the leadership team; hiring a Director of CX Optimization & Experimentation.
- **Cybersecurity**: Hiring a Director of Cybersecurity, suggesting scaling of digital infrastructure.

## Why Work Here
- **Culture & values**: Emphasizes five core values: *We Earn Trust*, *We Fail/Learn Fast*, *We Deal in Facts*, *We Are a Team*, and *We Take Ownership*. Highly collaborative, data-driven, and accountability-focused environment.
- **Diversity & inclusion**: **67% of leadership positions held by women**; **35 nationalities** represented on the team.
- **Flexibility**: Offers a **remote work program** and opportunities to work remotely when necessary (though primary HQ is Toronto office-based).
- **Travel perks**: Top performers receive **familiarization trips**; shared love of exploration is a core part of the culture.
- **Wellness & benefits**: Extended health coverage including employee assistance and wellness offerings; lunch-hour yoga classes; regular learning sessions.
- **Compensation**: Industry-leading salaries, **RRSP matching program**, referral bonuses, and recognition rewards.
- **Community impact**: Active volunteer program (Kensington Cares) — supports local charities and global causes.
- **Growth & training**: Committed to career advancement with ongoing training and development opportunities.
- **Team composition**: 1,430 total years of travel industry experience among staff; strong talent pipeline from companies like Travel Edge, Flight Centre, Navigatr, and G Adventures.

## Sources
1. [kensingtontours.com](https://www.kensingtontours.com/careers)
2. [linkedin.com](https://www.linkedin.com/company/kensington-tours)
3. [job-boards.greenhouse.io](https://job-boards.greenhouse.io/kensingtontours/jobs/5047598007)
4. [cbinsights.com](https://www.cbinsights.com/company/kensington-tours)
5. [builtin.com](https://builtin.com/company/kensington-tours)

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