VP, Corporate Fleet Sales in Schaumburg, Illinois at Wheels, Inc.

JOB OVERVIEW

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

KEY RESPONSIBILITIES - ESSENTIAL FUNCTIONS

• 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

LEADERSHIP RESPONSIBILITIES

Number of Direct Reports:

• 3

Number of Indirect Reports:

• 16

Budget/PNL Responsibility:

Full P&L ownership for the corporate fleet sales function

Leadership Responsibilities Strategy:

• Set the vision and direction for the corporate fleet sales organization, aligning team priorities to overall company growth objectives
• Lead and develop a high-performing sales team, establishing a culture of accountability, ownership, and continuous improvement
• Drive performance through clear goals, pipeline discipline, and consistent coaching on complex deal strategy
• Build and maintain a strong leadership bench by attracting, developing, and retaining top sales talent
• Operate as an executive leader, contributing to broader commercial strategy and organizational decision-making
• Serve as a trusted voice with the CEO, CFO, and investor audiences on commercial performance, market dynamics, and growth opportunities
• Lead by example in client engagement, particularly in high-value, strategic pursuits and executive-level relationships
• Champion a customer-centric mindset, ensuring client needs and outcomes are central to all sales activities
• Promote a culture that reflects company values, including integrity, collaboration, and innovation

COMPETENCIES - SKILLS

• 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.

EDUCATION AND EXPERIENCE

• Bachelor's degree required; MBA preferred
• 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

CORE VALUES

At Wheels, we believe in fostering a culture that is built on our Core Values and Guiding Principles. We cultivate a culture of excellence and innovation by upholding these values, driving our collective success and growth.

• Integrity – Always act with integrity and honesty.
• One Team – Treat others with dignity and respect; act as a cohesive, inclusive and accountable team that is making a difference.
• Innovation – Drive continuous improvement, spark creativity and embrace next generation thinking.
• Customer Success – Ensure that customer and driver success is at the heart of everything we do.

CULTURAL ATTRIBUTES

At Wheels, leaders are expected to model and champion our cultural attributes through their actions:

• Discipline Drives Quality – Plan the Trip: Think proactively, hold a high bar, follow through by leveraging experience and systems. To produce quality outcomes, we must be intentional and deliberate in everything we do, from big bets to daily execution.
• Intellectually Curious – Fuel Your Minds: Be bold, challenge assumptions, think differently, look outside the box. Strive to unlock your own thinking and create new possibilities.
• Commit and Deliver – Own It: Take responsibility for your work, from start to finish, and be accountable for the results. Think and act like an owner of the business.
• Relationships Matter – Share the Ride: Trust is central, both with key internal and external stakeholders. Relationships are not a side effect of work but a driver of success.

JOB SPECIFICATIONS, PHYSICAL DEMANDS AND WORK ENVIRONMENT

Work Environment: This is a hybrid position located in Georgia or Illinois and operates in a professional office environment.
Position Type/Standard Schedule: This is a full-time position, Monday through Friday.
Travel: Travel is expected 80% of the time.
Physical Demands: Speak, hear, and see, and to use hand and fingers for computer keyboard and phone. Sit or stand for extended periods of time. Reach above head to pull paper attachments.

DISCLAIMER

Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities that are required of the employee for this job. Duties, responsibilities, and activities may change at any time with or without notice.

Wheels recognizes benefits are a significant part of your employee experience, and we've created a robust benefits package that is market-leading, competitive offerings so you and your family can receive outstanding care. Please click here for an overview of the benefits available to you and your family.

Pay Range:

The base salary range for this position is listed above. This position is eligible to participate in the annual incentive plan which is based on company performance and individual performance. Compensation ranges are based on several factors including geographic location. Final offer amounts are determined by factors including, but not limited to, experience, credentials, education, certifications, skill level required for the position, the scope of the position, and geographic location. Actual pay offered will be determined on a case-by-case basis.

Wheels applies AI-based analysis to application materials to help assess fitness for hire for the specific job being applied for and to recommend job postings that align with the candidate’s skills, by comparing the candidate’s skills to the characteristics and qualifications listed in job postings and/or criteria established by Wheels’ hiring team.

As one of the largest fleet management companies in North America, Wheels features a portfolio of 900,000+ vehicles under management across the continent, a global alliance in 61 countries, and a client base that consists of some of the best-known businesses in the world. No matter the industry type or business size, we’re proud to work across sales and service fleets, trucks and equipment, and last mile delivery to ensure we power your potential.

The culture at Wheels is the secret to our 80+ years of success. And the reason people choose to join — and stay with — our team.

When you join the team, you'll work with professionals who are passionate, friendly and smart. We foster a welcoming and inclusive environment for all, combined with the encouragement to continuously learn and grow. From day one, we invest in your long-term development through annual performance goals and reviews, educational and wellness programs, awards and celebrations, and more.

Ready to experience the Wheels culture for yourself?

• 10 years average employee tenure

• 10 times recognized as one of Chicago's Best and Brightest Companies to Work For

• 50+ health, wellness and engagement benefits

• 2,500+ online learning programs

Diversity: Wheels deeply values the strength of diversity both in the communities we serve and our own employee base. This includes treating everyone as equal, respecting and valuing diversity, providing equal opportunity and fostering a safe space to work.

Community: We are heavily involved in the communities where we operate. We offer opportunities for employees to make a positive impact through mentorship and tutoring elementary school students, participating in blood drives, donating to United Way and other charitable organizations in the greater Chicagoland and Toronto areas.

Sustainability: Wheels is actively committed to becoming a cleaner fleet management company through recycling programs, public transportation support and more.

We Are Dedicated to the Safety and Health of our Employees

Our employees are critical to delivering on our commitment to client success, which is why we offer a variety of programs focused on the health and wellness of our people.

We hire people who have a customer-focused mindset and a strong collaborative nature. Because at Wheels, customer service and teamwork don't just happen in the office. It is during the informal moments when employee trust is strengthened and friendships are made. We value these moments, which is why we host departmental contests, summer gatherings, family events, holiday celebrations and more.

At Wheels, your well-being is our priority. As part of our commitment to your health and well-being, we’re proud to offer access to the Advocate Health Care Wellness Portal—a personalized platform designed to help you take charge of your health journey.

The 2026 Wellness Program is designed to support you in achieving your personal health goals. Best of all, it’s flexible and fits into your busy lifestyle.

This program is designed to support your overall well-being—physically, emotionally, and financially—by providing tools and incentives that encourage healthy living.