Kensington
Travel & HospitalityDirect Greenhouse career site

Director, Sales - Outside Sales, Midwest

Pay
$140,000 – $170,000 per year
Location
Remote (US)
Job type
Full-time
Level
Director
Listed
31 days ago

Skills & highlights for this role

  • Valid driver's license
  • Valid passport
  • B2B sales
  • account management
  • sales negotiation

Also useful

  • retail travel industry

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.

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 West PA, MI, OH)

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.

Pay and benefits

We provide a competitive compensation package with a strong pay for performance rewards approach. Employees have the opportunity to participate in incentive programs and compensation tied to business and individual performance. The expected compensation range for this position is: base plus commissions and bonus ($140-170K OTE). #LI-Remote

The actual compensation may vary depending on local market conditions, geography 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.

Read the original posting

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

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Common questions

What is the salary for the Director, Sales - Outside Sales, Midwest role at Kensington?

The Director, Sales - Outside Sales, Midwest posting at Kensington states compensation of $140,000 – $170,000 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 Director, Sales - Outside Sales, Midwest job at Kensington located?

Yes, this Director, Sales - Outside Sales, Midwest opening at Kensington is listed as Remote (US). Always check Kensington's application page for specific state eligibility or relocation policies.

What qualifications are required for Director, Sales - Outside Sales, Midwest at Kensington?

For the Director, Sales - Outside Sales, Midwest role, Kensington highlights experience with B2B sales, account management, sales negotiation. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.

How do I apply for the Director, Sales - Outside Sales, Midwest 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.