Lease Sales Representative

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 [https://www.gopenske.com/] to learn more.

The Lease Sales Representative will prospect, develop, and close new business opportunities within an assigned territory while building strategic relationships with C-suite executives. They will act as a trusted transportation consultant, leveraging data-driven tools to deliver customized solutions and manage the full sales cycle.

Candidates must have 5+ years of executive-level sales experience, preferably in transportation or logistics, and possess a valid Class 5 Driver's license. A high school diploma is required, while a bachelor's degree in business, sales, or marketing is preferred.

• 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

• Time managementPreferred
• SalesPreferred
• LogisticsPreferred

Identified from the job description. Confirm important requirements above.

• Sales
• B2B sales
• Consultative selling
• Strategic partnerships
• Cold calling
• Negotiation
• Executive communication
• CRM
• Salesforce
• Fleet management
• Logistics
• Transportation
• Pipeline management
• Business acumen
• Time management
• Relationship building
• Influencing Skills
• Customer Success Management
• Sales Prospecting
• Curiosity
• Deal Structuring
• Resilience
• Self-Motivation
• Business To Business
• Customer Relationship Management
• Business Acumen
• Management
• Cold Calling
• Communication
• Consultative Selling
• Training And Development
• Growth Strategies
• Innovation
• Operations
• Sales Process
• Sales Operations
• Strategic Partnership
• Value Propositions
• Revenue Growth
• Identifying Leads

• Sales
• Transportation
• Logistics
• Consulting
• Management & Leadership
• Lease Sales Representative
• Sales Representative (General)
• Commercial Sales Representatives
• Sales Representatives, Wholesale and Manufacturing, Except Technical and Scientific Products

Minimum education

High school

Minimum experience

5+ years

Posting language

English

Working hours

40 hours per week