Lease Sales Strategist — Car-Provided Vehicle & Growth Path

Penske; Honolulu (HI); On-site; USD 65,000 - 85,000; Full time

Benefits offered by this job

Competitive base salary + commission

Company-provided vehicle

Comprehensive training

Best-in-class sales technology

Comprehensive medical/dental/vision

Retirement plans

Paid sick days

Flexible, supportive work structure

Advancement opportunities

Job summary

Penske Truck Leasing/Transportation Solutions in Honolulu, HI is seeking a results-driven Lease Sales Representative to own a territory, negotiate complex leasing agreements, and deliver tailored transportation solutions. You will build executive relationships, drive revenue, and leverage Penske technology to optimize client operations.

The role emphasizes strategic selling, data-driven reviews, and cross-functional collaboration with sales and operations, with a competitive base plus commission

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 the operation of 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, 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

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

Skills

Executive sales experience

Executive-level communication

Consultative selling

CRM proficiency

Time management

Education

Bachelor's degree in Sales/Marketing or related field

High School Diploma or equivalent

Tools

Sales CRM

Microsoft Office (Word, Excel, PowerPoint, Outlook)

Job description

Penske Truck Leasing/Transportation Solutions in Honolulu, HI is seeking a results-driven Lease Sales Representative to own a territory, negotiate complex leasing agreements, and deliver tailored transportation solutions. You will build executive relationships, drive revenue, and leverage Penske technology to optimize client operations.

The role emphasizes strategic selling, data-driven reviews, and cross-functional collaboration with sales and operations, with a competitive base plus commission