Lease Sales Representative - Business Development / B2B

About the Role

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, 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.

Responsibilities

• 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

Requirements

• 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
• 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 operating a variety of computer software programs, including Microsoft Word, Excel, PowerPoint, Outlook, and Sales CRM
• High School Diploma or equivalent required; bachelor’s degree in Sales, Marketing, or related field preferred
• Valid Driver’s license required
• Regular, predictable, full attendance is an essential function of the job
• Willingness to travel as necessary and work the hours required to accomplish job duties

Benefits

• 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
• Retirement plans
• Paid sick days and employee referral bonuses
• Flexible, supportive work structure
• Real advancement opportunities across sales, operations, and more

Pay

$65,300-$84,900/yr

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.

Address: 819 Ahua St., Honolulu, HI