Lease Sales Representative in Winnipeg

We're looking for someone who is motivated, curious, and ready to make an impact. 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.
• 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 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.
• 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.
• 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 a 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, and complete Penske employment application.

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.