About The Position

Penske is seeking a motivated Lease Sales Representative to develop strategic business partnerships and drive revenue growth within an assigned territory. The representative manages their own time and priorities, builds executive-level relationships, and acts as a trusted transportation consultant. They use Penske’s technology, analytics, and industry insights to identify customer needs and deliver customized solutions that improve business operations and efficiency. The role focuses on prospecting, developing, closing, and retaining B2B leasing and transportation business. The representative works with customers and internal teams to qualify opportunities, negotiate agreements, expand relationships across Penske’s product lines, and provide seamless service delivery. The position includes field-based sales activity, customer meetings, and industry events, as well as proactive pipeline and territory management using Salesforce and other business tools.

Requirements

  • At least 5 years of executive-level sales experience, or experience in a sales support role with executive-level customer exposure.
  • Proven success meeting or exceeding sales quotas in competitive, field-based B2B sales environments; transportation, logistics, fleet management, or service sales experience is preferred.
  • Demonstrated consultative and strategic selling ability, including presenting multiple products and services verbally and in writing to C-level executives.
  • Strong executive-level communication, negotiation, and relationship-building skills, with the ability to influence decision-makers and close complex, multi-party deals.
  • Business acumen to understand customer needs and financial impacts and identify growth opportunities.
  • Proficiency with CRM systems and data-driven tools, and ability to manage a pipeline, territory, time, and competing priorities effectively.
  • Ability to collaborate across internal teams and remain resilient through long sales cycles.
  • Skill operating computer software including Microsoft Word, Excel, PowerPoint, Outlook, and sales CRM software.
  • High school diploma or equivalent required.
  • Valid driver’s license required.
  • Regular, predictable, full attendance is an essential function of the job.
  • Willingness to travel as necessary, work the hours necessary to accomplish job duties, and work at the required location.
  • Must complete a Penske employment application and submit to a background investigation, including past employment, education, and criminal history, and drug screening.

Nice To Haves

  • Bachelor’s degree in Sales, Marketing, or a related field preferred.
  • Experience in transportation, logistics, fleet management, or service selling.

Responsibilities

  • Prospect, develop, and close new, add-on, and retention opportunities in an assigned territory to meet annual quota targets.
  • Identify leads through cold calling, networking, and referrals across Penske product lines, including Penske Trailer Plus, Fleet Management, Logistics, and On-Site services.
  • Build and maintain strategic relationships with C-suite executives and other key decision-makers.
  • Understand customer operations and provide transportation insights and solutions that improve business outcomes.
  • Negotiate leasing and maintenance agreements that create value for customers and Penske.
  • Conduct partnership reviews using Salesforce, fleet analytics, and business insights tools to identify growth opportunities and expand customer relationships across product lines.
  • Collaborate with internal teams and Corporate Sales early in the sales process to present Penske’s value proposition, align on growth strategy, and support service delivery.
  • Qualify opportunities by assessing customer fit, deal structure, and long-term partnership potential.
  • Represent Penske at industry events, trade shows, and client meetings.
  • Monitor industry trends, competitors, and regulatory changes to position solutions effectively.
  • Manage the sales pipeline using Salesforce and maintain communication with prospects and customers throughout the sales cycle.

Benefits

  • Competitive base salary plus performance-based commission
  • Company-provided vehicle for business and personal use
  • Comprehensive training and development from day one
  • Best-in-class sales technology
  • Medical, dental, and vision coverage
  • Retirement plans
  • Paid sick days
  • Employee referral bonuses
  • Flexible, supportive work structure
  • Advancement opportunities across sales, operations, and other areas
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