VP, Corporate Fleet Sales

Wheels, Inc. • Schaumburg, IL

18d • $209,000 - $292,500 • Hybrid

About The Position

Reporting to the Chief Commercial Officer, this role leads the Strategic Sales organization for Wheels, with primary responsibility for achieving corporate fleet sales targets, driving revenue growth, and managing the P&L for the corporate fleet sales function. This leader will serve as a key commercial executive, engaging directly with senior leadership, board members, and investors on growth strategy and business performance.

Requirements

• Bachelor's degree required
• Fifteen (15) years of progressive experience in sales, preferably in fleet management, mobility, or related industries
• Ten (10)+ years of leadership experience, including managing sales leaders and scaling high-performing teams
• Proven track record of achieving revenue targets and managing P&L accountability in complex, enterprise sales environments
• Experience presenting to and engaging with C-suite executives, board members, and/or investors on commercial strategy and business performance
• Experience leading sales strategy, pipeline development, and forecasting at an organizational level
• Experience navigating and leading through change, including scaling teams, entering new markets, or evolving go-to-market models
• Experience leading complex, enterprise-level sales environments with long sales cycles and multi-stakeholder decision processes
• Intermediate to advanced proficiency in Microsoft Office tools including Outlook, Word, Excel, and PowerPoint.

Nice To Haves

• MBA preferred

Responsibilities

• Define and execute the corporate fleet sales strategy to achieve revenue growth and market expansion targets
• Own and manage the corporate fleet sales P&L, including revenue, margin, and cost performance against plan
• Own and deliver against annual sales goals, pipeline development, and forecast accuracy
• Lead the pursuit and closure of large, complex, multi-year enterprise fleet deals, including oversight of pricing, credit risk, and deal structure
• Build and maintain executive-level relationships with key clients and prospects
• Engage with senior leadership, board members, and investors to communicate commercial strategy, growth trajectory, and portfolio performance
• Develop and lead a high-performing sales team, including coaching, performance management, and talent development
• Drive solution-based selling by aligning fleet strategies to client business objectives (e.g., cost, productivity, driver experience)
• Partner cross-functionally with operations, finance, legal, and credit to structure competitive, scalable client solutions that appropriately balance growth with risk
• Establish disciplined sales processes, CRM usage, and pipeline governance across the organization
• Support strategic account growth through renewals, expansions, and executive engagement
• Represent the company in the market, contributing to thought leadership and go-to-market strategy
• Performs other duties as assigned

Benefits

• Annual incentive plan which is based on company performance and individual performance
• 50+ health, wellness and engagement benefits
• 2,500+ online learning programs

What This Job Offers

• Job Type: Full-time
• Career Level: Executive