ALL IN ON A REWARDING CAREER AT INLAND Inland Kenworth is an industry leader in the heavy‑duty truck sales, service, and parts marketplace. When we say we’re ALL IN, we mean we’re all in on you and your career.

Join us at Inland Kenworth and go ALL IN on a career that has it all.

THE OPPORTUNITY The Fleet Remarketing Specialist – Outside Sales is responsible for

field‑based sourcing, prospecting, purchasing, and selling

used trucks. In this position, you will spend your time selling, obtaining orders, negotiating pricing, and making sales or purchase contracts

with customers, fleets, wholesalers, and dealerships. The Fleet Remarketing Specialist also evaluates trucks for purchase, trade‑in, or resale and recommends pricing and terms.

SALARY + COMMISSION

This position is paid a base salary plus commission with an uncapped commission opportunity and first year on-target earnings (OTE) of $100,000 - $120,000

YOUR RESPONSIBILITIES Outside Sales Responsibilities

Spends 50% or more of working time away from the employer’s place of business

performing sales activities.

Conducts in‑person prospecting

with fleets, dealerships, wholesalers, and end‑users.

Visits customer locations, fleet yards, auctions, and off‑site facilities

to inspect equipment, present inventory, negotiate pricing, and close deals.

Obtains orders and executes sales or purchase contracts

during field visits.

Develops and maintains customer relationships

through regular in‑person meetings.

Delivers vehicles directly to customer locations

and reviews features, terms, and conditions.

Represents Inland in the field as the primary point of contact for wholesale purchasing and selling opportunities.

Wholesale – Purchasing

Actively prospects for used trucks through in‑person visits and field networking.

Develops relationships with fleets and dealerships as equipment sources.

Travels to inspect trucks for purchase, trade‑in, or repossession.





Analyzes equipment and collaborates with the Director on valuations.

Monitors auctions, customer yards, and online platforms for opportunities.

Coordinates transportation of purchased trucks.

Completes administrative steps for funding and documentation.

Adheres to Inland guidelines for purchase limits and approvals.

Fleet Remarketing

Prospects in the field to sell individual units and truck groups.

Conducts

on‑site demonstrations and presentations

for customers.

Assists customers in selecting vehicles based on needs and inspection results.

Writes sales orders and processes paperwork per dealership policy.

Ensures sold vehicles meet agreed‑upon conditions.

Supports the New Truck Department with remarketing fleet trades.

Customer Relations & Delivery

Follows up on post‑delivery items and customer requests.

Maintains a follow‑up system to encourage repeat and referral business.

Maintains a professional appearance and customer‑focused approach.

Planning & Productivity

Sets personal income goals aligned with dealership standards.

Maintains a consistent schedule of

field cold calls , customer visits, and pipeline development.

Reviews performance regularly to improve efficiency.

Attends meetings and maintains a clean work environment.

Complies with company Health & Safety policies.

WHAT WE LOOK FOR

Post‑secondary education in sales/marketing preferred.

Excellent sales skills, with demonstrated sales experience selling in a business‑to‑business environment





Medium/heavy‑duty truck sales experience preferred.

Automotive sales experience an asset.

Three years of related experience or equivalent combination.

Proficiency in Microsoft Word and Excel.

Valid driver’s license required; commercial classification preferred.

Proven ability to develop and work a sales and fleet remarketing action plan and drive to achieve results

Ability to negotiate is essential

Have a valid Driver’s License and be able to travel in your personal vehicle (mileage reimbursement included and expenses reimbursable),commercial classification preferred

Must be able to climb into and out of commercial transport vehicles

Travel outside of the local area will be required from time to time, typically generated by meetings at Inland branches, training programs or seminars, along with trips to vendor and OEM locations. This may include travel in both Canada and the USA, so it is essential you hold and maintain a valid driver’s license and passport at all times and be able to travel as required.

US BENEFITS PACKAGE Our employees receive a generous benefits package including:

Medical

Dental

Vision

Prescription advantages

401k with employer matching program

Flexible Savings Account

Health Savings Account (available with some medical programs)

Long Term and Short-Term Disability

Life Insurance and Accidental Death and Dismemberment Insurance

Paid Time Off

On‑going training opportunities

ABOUT INLAND KENWORTH We are a excellent place to work—with competitive pay and benefits, mentorship, growth opportunities, and a culture that prioritizes teamwork, safety, and community support. We are committed to embracing new technology, ensuring that we stay at the forefront of innovation in our industry. With 2,000 employees across 50 locations in North America, we provide exciting employment opportunities that can drive your future growth.

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📌 Fleet Remarketing Specialist (Winnipeg)
🏢 Socket.dev
📍 Winnipeg