Penske

Diversified transportation, logistics, and motorsports provider

Lease Sales Representative

Field SalesConfirmed live in the last 24 hours

Full-timeWinnipeg, MB, CanadaIn-person

About the Job

Requirements

Proven success in meeting or exceeding sales quotas in competitive, field-based business-to-business environments, preferably in transportation, logistics, or fleet management.
Strong executive-level communication and negotiation skills, including the ability to influence C-suite stakeholders and close complex, multi-party deals.
A consultative selling approach and business acumen to understand customer needs and financial impacts and uncover growth opportunities.
Proficiency with customer relationship management systems and data-driven tools, including the ability to manage a pipeline, territory, and time effectively.
Self-motivation, adaptability, collaboration, resilience in long sales cycles, and the ability to work cross-functionally with internal teams.
At least five years of executive-level sales experience or experience in a sales support role with executive-level customer exposure; service and transportation selling experience is preferred.
A full Class 5 driver's license.
A high school diploma or equivalent is required.
Demonstrated ability in consultative and strategic selling, including experience presenting multiple products and services verbally and in writing to C-level executives.
Ability to build rapport and relationships with internal and external customers at all levels.
Strong organizational and time-management skills, including the ability to prioritize multiple projects and work streams.
Skill in operating computer software including Microsoft Word, Excel, PowerPoint, Outlook, and sales customer relationship management software.
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, and work at the required specific location.
Completion of the Penske employment application, background investigation (including past employment, education, and criminal history), and drug screening are required.
Ability to read; communicate verbally and/or in writing; remember and analyze information; and remember and understand instructions or guidelines.
Ability to stand, walk, and sit; frequently use hands to touch, handle, and feel; reach with hands and arms; and occasionally lift or move up to 25 pounds/12 kilograms.
Required vision abilities include close vision, distance vision, peripheral vision, depth perception, and the ability to adjust focus.

Responsibilities

Prospect, develop, and close new, add-on, and retention opportunities within the assigned territory to meet annual quota targets, identifying leads through cold calling, networking, and referrals across Penske product lines.
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 providing insights to improve business outcomes.
Negotiate complex leasing and maintenance agreements that create mutual value for customers and Penske.
Conduct regular partnership reviews using data-driven intelligence, 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 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 the network and market presence.
Stay informed about industry trends, the competitive landscape, and regulatory changes to position solutions effectively.
Manage the sales pipeline proactively using Salesforce and maintain consistent communication with prospects and customers throughout the sales cycle.

Desired Qualifications

Experience in transportation, logistics, or fleet management is preferred.
A bachelor's degree in Business, Sales, Marketing, or a related field is preferred.

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.

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

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

Salary + Commission + Company Car

Why Join Penske?

Making a living while also enjoying the living part of life. We make sure you are compensated well and have the support you need to grow, stay healthy and maintain a good work-life balance.

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 the Company

Penske

Diversified transportation, logistics, and motorsports provider

Penske provides a range of transportation services, including retail automotive sales and service, truck leasing and rental, and logistics solutions, plus professional motorsports activities. Its offerings work through distinct units: Penske Automotive Group sells and services vehicles, Penske Truck Leasing rents and maintains trucks with fleet management, and Penske Logistics handles end-to-end supply chain services. The company differentiates itself by operating multiple transportation and entertainment businesses under one private global umbrella, enabling cross-sell opportunities and large-scale coordination. Its goal is to deliver reliable, end-to-end transportation and logistics solutions for individuals and businesses worldwide while growing its diversified portfolio and leveraging scale.

Company size: 501-1,000
Company stage: Not listed
Total funding: Not listed
Headquarters: Bellflower, CA
Founded: 1969

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