Lease Sales Representative

Penske Truck Leasing; Winnipeg; On-site; CAD 65,000 - 90,000; Full time

Benefits offered by this job

Company car

Benefits including medical, dental, &视

RRSP matching

Training and development

Paid sick days

Growth opportunities

Job summary

Penske Truck Leasing in Winnipeg is seeking a motivated Lease Sales Representative to own your territory and drive revenue growth by delivering customized transportation solutions. You will build executive-level relationships and serve as a trusted transportation consultant leveraging Penske's technology and insights to improve client operations.

Join a fast-paced, results-driven team with base salary plus commission, a company car, comprehensive benefits, and ongoing training.

Qualifications

• 5+ years of executive-level sales experience, preferably in B2B transportation/Logistics.
• Active driver's license (Class 5) and willingness to travel.
• HS diploma required; Bachelor's degree preferred in business, sales, or marketing.
• Ability to present to C-level executives and articulate multiple products/services in writing and verbally.
• Strong organizational skills and ability to manage multiple projects and prioritize.

Responsibilities

• Prospect, develop, and close new and retention opportunities within the territory to meet annual quota across Penske product lines.
• Build and maintain strategic relationships with C-suite executives and key decision-makers.
• Act as a transportation consultant to understand customer operations and deliver insights.
• Negotiate lease and maintenance agreements creating mutual value.
• Use data-driven insights and Salesforce to identify growth opportunities and expand share of wallet.

Skills

Executive-level sales

Consultative selling

CRM proficiency

Time management

Self-motivated

Education

High School Diploma or equivalent

Bachelor's degree in Business or related field

Tools

Sales CRM (Salesforce)

Microsoft Office Suite

Job description

We're looking for someone who is motivated, curious, and ready to make an impact.

Ready to Launch Your Sales Career with a Winning Team?

Join a fast paced, results-driven sales environment where your expertise drives strategic partnerships and revenue growth. As a Lease Sales Representative, you'll own your territory, while operating with a high level of self-motivation and personal responsibility for managing your time and priorities. You'll build executive-level relationships and deliver customized solutions that help businesses improve operations, increase efficiency, and solve complex challenges. You'll act as a trusted transportation consultant, leveraging Penske's industry-leading technology and insights to solve complex business challenges.

Location: 1100 King Edward St, Winnipeg, MB R3H 0R2

Salary + Commission + Company Car

Why Join Penske?

• Competitive base salary + performance-based commission
• A company-provided vehicle for both business and personal use
• Comprehensive training and development from day one
• Best-in-class sales technology that gives you a competitive edge in the market
• Comprehensive benefits including medical, dental, and vision coverage
• Group RRSP with up to 5% employer match
• Paid sick days and employee referral bonuses
• Flexible, supportive work structure
• Real advancement opportunities across sales, operations, and more

What You’ll Do

• Prospect, develop, and close new, add, and retention opportunities within your assigned territory to meet annual quota targets, including identifying leads through cold calling, networking, and referrals across Penske's diverse product lines (Penske Trailer Plus, Penske Fleet Management, Logistics, On-Site, etc.)
• Build and maintain strategic relationships with C-suite executives and key decision-makers to drive long-term partnerships
• Act as a trusted transportation consultant by understanding customer operations and delivering insights that improve their business outcomes
• Negotiate complex leasing and maintenance agreements that create mutual value for customers and Penske
• Conduct regular partnership reviews using data-driven intelligence - leveraging Salesforce, fleet analytics, and business insights tools - to identify growth opportunities and expand share of wallet across product lines
• Collaborate with internal teams and the Corporate Sales team early in the sales process to articulate Penske's full value proposition, align on growth strategy, and ensure seamless service delivery
• Qualify opportunities by evaluating customer fit, deal structure, and long-term partnership potential
• Represent Penske at industry events, trade shows, and client meetings to expand your network and market presence
• Stay informed on industry trends, competitive landscape, and regulatory changes to position solutions effectively
• Manage your pipeline proactively using Salesforce and maintain consistent communication with prospects and customers throughout the sales cycle

What You Bring

• Proven success in meeting or exceeding sales quotas in competitive, field-based B2B environments, preferably in transportation, logistics, or fleet management
• Strong executive-level communication and negotiation skills, with the ability to influence C-suite stakeholders and close complex, multi-party deals
• Consultative selling approach with business acumen to understand customer needs, financial impacts, and uncover growth opportunities
• Proficiency with CRM systems and data-driven tools, with the ability to manage pipeline, territory, and time effectively
• Self-motivated, adaptable, and collaborative, with resilience in long sales cycles and the ability to work cross-functionally with internal teams

Qualifications

• 5+ years of executive level sales experience or experience in a sales support role with executive level exposure to customers, preferably in a service and transportation selling environment
• Full Class 5 Driver's license
• High School Diploma or equivalent required bachelor's degree in business, Sales, Marketing, or related field preferred
• Demonstrated ability in consultative and strategic selling techniques, including previous experience in articulating / presenting multiple products and services to C-level executives both verbally and in writing
• Ability to connect and build rapport / relationships with internal and external customers at all levels
• Strong organizational skills, time management skills, and the ability to prioritize multiple projects / work streams
• Skill in the operation of variety of computer software programs, including Microsoft Word, Excel, PowerPoint, Outlook, and Sales CRM
• Regular, predictable, full attendance is an essential function of the job
• Willingness to travel as necessary, work the hours necessary to accomplish the job duties, work at the specific location required, complete Penske employment application, submit to a background investigation (to include past employment, education, and criminal history) and drug screening required.

Join Penske and be part of something bigger - where your drive opens the door to real opportunity.

Physical Requirements

• The physical and mental demands described here are representative of those that must be met by an associate to successfully perform the essential functions of this job. Reasonable accommodation may be made to enable individuals with disabilities to perform the essential functions.
• The associate will be required to: read; communicate verbally and/or in written form; remember and analyze certain information; and remember and understand certain instructions or guidelines.
• While performing the duties of this job, the associate may be required to stand, walk, and sit. The associate is frequently required to use hands to touch, handle, and feel, and to reach with hands and arms. The associate must be able to occasionally lift and/or move up to 25lbs/12kg.
• Specific vision abilities required by this job include close vision, distance vision, peripheral vision, depth perception and the ability to adjust focus.

About Penske Truck Leasing/Transportation Solutions

Penske Truck Leasing/Transportation Solutions is a premier global transportation provider that delivers essential and innovative transportation, logistics and technology services to help companies and people move forward. With headquarters in Reading, PA, Penske and its associates are driven by a dedication to excellence and a commitment to customer success. Visit Go Penske to learn more.

Penske is committed to the principle of equity in employment.