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Added 2 mins ago
NC
Housing Support Worker
Neighbours Community Homes
Canada
- Full-time
Appear as a representative of the landlord and a witness at Ontario Landlord and Tenant Board hearings.
Added 32 mins ago
P
Sales and Operations Management Trainee
Penske
Surrey, BC
- Full-time
…environment, you will use your hard-earned degree to run a business and quickly solve problems for our customers – who will depend on you to achieve…
Added 32 mins ago
P
Sales and Operations Management Trainee
Penske
Quebec, QC
- Full-time
Schedule: Monday to Friday. Business hours are 6:30 AM to 5:00 PM. The successful candidate must be available to work an 8-hour shift scheduled within these operating hours.
Added 32 mins ago
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District Financial Manager
Penske
Delta, BC
- Full-time
Responsible for planning, organizing and otherwise preparing Business Plan by leading the district staff to complete the sales plan, vehicle inputs, payrolls, draft presentation slides etc.…
Added 32 mins ago
P
Sales and Operations Management Trainee
Penske
London, ON · Stoney Creek, ON
- Full-time
…environment, you will use your hard-earned degree to run a business and quickly solve problems for our customers – who will depend on you to achieve…
Added 32 mins ago
P
Lease Sales Representative
Penske
Winnipeg, MB
- Full-time
…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…
Added 32 mins ago
P
Bilingual Sales and Operations Management Trainee Montreal Quebec City
Penske
QC · QC, Canada
- Full-time
…environment, you will use your hard-earned degree to run a business and quickly solve problems for our customers – who will depend on you to achieve…
Added 32 mins ago
P
Sales and Operations Management Trainee
Penske
Cambridge, ON
- Full-time
…environment, you will use your hard-earned degree to run a business and quickly solve problems for our customers – who will depend on you to achieve…
Added 32 mins ago
P
Sales and Operations Management Trainee
Penske
Mississauga, ON
- Full-time
…environment, you will use your hard-earned degree to run a business and quickly solve problems for our customers – who will depend on you to achieve…
Added 32 mins ago
P
Sales and Operations Management Trainee
Penske
Toronto, ON · Scarborough, ON
- Full-time
…environment, you will use your hard-earned degree to run a business and quickly solve problems for our customers – who will depend on you to achieve…
Added 32 mins ago
P
Sales and Operations Management Trainee
Penske
Surrey, BC
- Full-time
…environment, you will use your hard-earned degree to run a business and quickly solve problems for our customers – who will depend on you to achieve…
Added 32 mins ago
P
Load Planner - Day Shift - 14 to 20 Month Contract
Penske
Kitchener, ON
- Full-time
This role supports development of the logistics design plan for customers inbound supply chain network. The Load Planner creates instructions for internal groups and the customer’s…
Added 3 hours ago
H
Manager Medical Device Reprocessing Saskatoon City Hospital
HealthCareersInSask.ca
Saskatoon, SK
- Full-time
…objectives of the SHA. The Manager supports strategy through the development and execution of operational and business plans, including cascading, monitoring, reporting, and course…
Added 3 hours ago
S
Clinic Transcription and Health Records Evaluator, TB Clinics - BC Centre for Disease Control
Sanya’k̓ula
Vancouver, BC
- Full-time
…cultural immersion experiences, and continuous professional development to stay informed and responsive to equity-deserving groups. Provide patient-centred care that respects Indigenous…
Added 3 hours ago
S
Social Worker (MSW), Heartwood Centre for Women, BC Mental Health & Substance Use Services - Vancouver, BC
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Vancouver, BC
- Full-time
Participate in program planning and development as part of an inter-professional team within BC Children’s Hospital and BC Mental Health and Addiction Services and the continuum of health…
Added 3 hours ago
CC
Student, Project Procurement
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- Full-time
…create a culture where inclusion is the goal, and a diverse and representative workforce is our measure of success. Cameco is committed to providing an inclusive selection process, free…
Added 3 hours ago
CC
Student, Asset Info Management
Cameco Corporation
Saskatoon, SK
- Full-time
…create a culture where inclusion is the goal, and a diverse and representative workforce is our measure of success. Cameco is committed to providing an inclusive selection process, free…
Added 3 hours ago
CC
Student, Information Management
Cameco Corporation
Saskatoon, SK
- Full-time
…create a culture where inclusion is the goal, and a diverse and representative workforce is our measure of success. Cameco is committed to providing an inclusive selection process, free…
Added 3 hours ago
CC
Student, Business Intelligence
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- Volunteer
Provide support in the development of dashboards and key performance indicator (KPI) metrics used to make business decisions.
Added 3 hours ago
FC
Member Service Representative (Part-Time)
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- Part-time
…Assists with achieving the goals and objectives relating to business development as set forth by the Branch…
Added 3 hours ago
C
Senior Account Manager - Financial Institutions
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Toronto, ON
- Full-time
Lead a team of account managers through coaching, development, and performance oversight
Added 3 hours ago
D
Personal Finance Advisor
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Repentigny, QC · Terrebonne, QC
- Full-time
As a personal finance advisor, you’re responsible for developing and maintaining lasting and trusting business relationships with members and clients, to ensure they’re satisfied. Your role…
Added 4 hours ago
CO
Building Servicer 2 - Aquatics
City of Winnipeg
Winnipeg, MB
- Full-time
…programs. Additionally, we offer education, training, and staff development opportunities to ensure that our employees are equipped with the necessary skills to advance in their…
Added 4 hours ago
CA
Machine Operator - Afternoon shift
Collins Aerospace
Oakville, ON
- Full-time
…businesses, world-class operations and investments in research and development, we offer capabilities and opportunity no one else can. Together, we push the boundaries of known science and…
Added 4 hours ago
Assistant Store Manager
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Penske

Lease Sales Representative

Winnipeg, MB, Canada

Full-time

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Job details

Job type: Full-time
Posting language: English
Posted: Oct 14, 2026

Original job description

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 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.

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More about this job

Responsibilities

The Lease Sales Representative will prospect, develop, and close new business opportunities within an assigned territory to meet annual quota targets. They will act as a trusted transportation consultant by building strategic relationships with C-suite executives and delivering customized leasing and maintenance solutions.

Requirements

Candidates must have 5+ years of executive-level sales experience, preferably in transportation or logistics, and possess a full Class 5 Driver's license. Proficiency in CRM software and strong consultative selling skills are essential for managing complex, multi-party deals.

Skills

Sales
Consultative selling
B2B sales
Negotiation
Relationship management
Pipeline management
Strategic planning
Fleet management
Logistics
Transportation
CRM
Salesforce
Data analysis
Communication
Time management
Business acumen

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

Visa sponsorship

Not detected in the job text

Keywords

Sales
Leasing
Transportation
Logistics
Fleet Management
B2B
Consultative Selling
Salesforce
CRM
Cold Calling
Networking
C-suite
Negotiation
Business Development
Account Management
Territory Management
Data-driven
Analytics
Trailer Plus
On-Site
Strategic Partnerships
Revenue Growth
Microsoft Office
Field Sales
Regulatory Compliance

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