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Lease Sales Representative
Job Location:
Monthly Salary:
Posted:
22 August 2026 (19 hours ago)
Posted:
Application Deadline:
19 November 2026
Application Deadline:
Vacancies:
1 Vacancy
Vacancies:
Job Summary
Description
Qualifications
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 youll own your territory while operating with a high level of self-motivation and personal responsibility for managing your time and priorities. Youll build executive-level relationships and deliver customized solutions that help businesses improve operations increase efficiency and solve complex challenges. Youll act as a trusted transportation consultant leveraging Penskes industry-leading technology and insights to solve complex business challenges.
Were 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 Youll 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 Penskes 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 Penskes 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
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 Drivers license
- High School Diploma or equivalent required bachelors 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.
Required Experience:
IC
About Company
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 headqu ... View more
