Lease Sales Representative
Winnipeg · On-site
About this role
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
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.
Company at a glance
Penske Truck Leasing is a Penske Transportation Solutions company headquartered in Reading, Pennsylvania. A leading provider of innovative transportation solutions, Penske operates and maintains nearly 400,000 vehicles and serves its customers from approximately 1,000 maintenance facilities and more than 1,900 truck rental locations across North America. Solutions from Penske include full-service truck leasing, fleet maintenance, truck rentals, used trucks, and a comprehensive array of technologies to keep the world moving forward. Penske Truck Leasing Co., L.P. is a partnership of Penske Corporation, Penske Automotive Group and Mitsui & Co., Ltd.
Founded1969
Team Size10,001+ employees
WorkspaceOn-site
IndustryTransportation, Logistics, Supply Chain and Storage
Location
Winnipeg, Manitoba, Canada
Websitepensketruckleasing.com
LinkedInLinkedIn
Top Benefits
- Competitive base salary
- Performance-based commission
- Company-provided vehicle
- Comprehensive training and development
- Medical coverage
- Dental coverage
- Vision coverage
- Group RRSP with employer match
- Paid sick days
- Employee referral bonuses
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