VP, Corporate Fleet Sales

Wheels•Schaumburg, IL

2d•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

Proven ability to lead and scale a high-performing sales organization, with full accountability for revenue growth, P&L management, and business performance
Strong strategic thinking skills, with experience defining and executing go-to-market plans, target segments, and growth strategies
Demonstrated success owning and delivering against team-based revenue targets, including pipeline development and forecast accuracy
Deep expertise in building and enforcing sales process discipline, including pipeline management, deal inspection, and CRM governance
Track record of hiring, developing, and retaining top sales talent, including coaching both individual contributors and frontline leaders
Strong commercial and financial acumen, with the ability to evaluate deal structures, pricing strategies, credit risk, and overall business impact
Ability to operate cross-functionally at an executive level, partnering with operations, finance, legal, marketing, and product to drive results
Excellent executive presence, communication, and influencing skills, with the ability to engage board members, investors, and senior stakeholders both internally and externally
Demonstrated ability to drive organizational alignment, accountability, and performance through clear goals and operating rhythms
Strong customer-centric mindset, with the ability to align sales strategy to client needs and long-term value creation
Intermediate to advanced proficiency in Microsoft Office tools including Outlook, Word, Excel, and PowerPoint.
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

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