Outside Sales Representative - Trailer Leasing & Fleet Services

Vault Consulting (Accounting, Human Resources, Research); Mississauga; Hybrid; CAD 75,000 - 105,000; Full time

Job summary

A leading consulting firm is looking for a Lease Rental Representative/Outside Sales to sell trailer rentals and leases. The role involves managing existing accounts and aggressively pursuing new business across Ontario. Candidates should have at least 3 years of outside sales experience and a mechanical aptitude. The position offers a competitive salary with commission, a car allowance, and a strong corporate culture focused on growth and mentorship.

Benefits

Competitive salary

Car allowance

Monthly gas card

Qualifications

• Established relationships in trailer leasing sectors preferred.
• Experience selling to fleet managers and logistics personnel is necessary.
• Strong work ethic and a positive attitude are essential.

Responsibilities

• Sell trailer rentals and leases to diverse clients.
• Manage existing rental accounts and pursue new business.
• Prepare rental contracts and perform trailer inspections.

Skills

Sales expertise

Relationship management

Mechanical aptitude

Education

3+ years of outside sales experience

Job description

Overview

As a Lease Rental Representative/Outside Sales, you will focus on selling trailer rentals and leases, including flatbeds, dry vans, and refrigerated trailers, to a diverse client base such as trucking companies, private fleets, and large corporations. This outside sales role involves nurturing a small portfolio of existing rental accounts while aggressively pursuing new business opportunities across various industries. You will also be responsible for trailer inspections and rental contract preparation. This role offers a competitive base salary with commission potential, a monthly car allowance, and additional benefits.

Compensation & Benefits

• Base Salary: 75,000 + Guaranteed commissions in the first year to 105,000
• Car allowance, gas card, 407 transponder

The Company & Culture

Our client provides managed commercial vehicle and maintenance services to retail chains, manufacturers, and distribution companies with commercial fleets that require maintenance across Canada. The company was founded in 2003 with a staff of over 225, and is growing by over 20-50% per year. Their corporate culture is entrepreneurial and results-focused with an authentic family feel. Their focus is to have an industry-leading culture with a focus on employee engagement. Current clients include Metro and Loblaws Grocery Chains.

Office Location & Sales Territory

• Primarily office-based with regular client visits
• No fixed geographical territory; focus on key accounts and new business development across Ontario
• Opportunity to gradually inherit and grow existing lease rental accounts including major clients like Sobeys, Metro, and Loblaws

Experience, Background & Education Requirements

• 3+ years of outside sales experience, preferably in truck or trailer leasing or rental
• Established relationships within the flatbed, dry van, or refrigerated trailer leasing sectors highly preferred
• Experience selling to fleet managers, dispatchers, transportation or logistics managers, and warehouse managers
• Mechanical aptitude or understanding of heavy-duty truck and trailer equipment is an asset
• Must have a reliable vehicle for travel and client visits
• Strong work ethic and positive attitude essential for success in a fast-paced, relationship-driven environment

Technical Skills

Ability to inspect trailers, prepare rental contracts

The Product / Service / Solution

• Lease and rental of flatbeds, dry vans, and refrigerated trailers to trucking companies, private fleets, and businesses with vehicle fleets needing temporary or long-term trailer solutions

Prospective Customers / Industry Focus / Decision Makers

• Dispatchers, Fleet Managers, Transportation Managers, Logistics Managers, Warehouse Managers
• Procurement Departments at trucking companies, private fleets, manufacturers, shippers, and large corporations
• Examples of target customers include Walmart, Canadian Tire, Sobeys, Metro, and Loblaws

Sales Cycle / Order Value / Account Size

• Average project size: 100 - 150 assets
• Average revenue per customer: $350,000 - $500,000
• Average sales cycle: 1 week to 12 months

Competitive Advantages

• Full-service fleet solutions (leasing + maintenance + breakdown support)
• In-house roadside service integration

Typical Day & Duties

• Manage 3 to 10 existing rental accounts with established relationships
• 50% new business development through prospecting and cold calling
• 50% follow-up on warm leads and nurturing potential clients

Leads

• Primarily self-generated prospecting/cold calling
• Some follow-up on warm leads from existing clients

Overnight Travel

• Minimal (<10%); mostly regional day travel

Support & Training

• Classroom/Online
• Job Shadowing/Joint sales calls
• Mentoring
• Off-site training (supplier tours, etc.)
• On-the-job internal work

Why You Should Apply

• High-growth opportunity in a new business expansion role
• Sell end-to-end solutions (leasing, maintenance, technology)
• Car allowance, gas card, and expense coverage
• Strong corporate culture with mentorship and career development

How to Apply

If this job is not ideal for you, please upload your resume for future considerations. Applications may be submitted through the employer’s or recruitment platform’s site. For additional opportunities, visit the employer’s careers page.