Field Sales Representative - Chicago

Field Sales Representative

Corpay is currently looking to hire a Field Sales Representative, within our Fleet division. This position falls under our North American Trucking line of business and is located in Chicago, Illinois. In this role, you will drive new business growth by acquiring and expanding mid-sized trucking fleet accounts within an assigned geographic territory. The representative functions as an in-market expert, responsible for developing direct relationships with fleet owners, operations leaders, and financial decision-makers. Primary objective : increase adoption of integrated payment and technology solutions that optimize fuel spend, cash flow, and operational control for carriers operating 21150 vehicles.

The position demands consistent in-person engagement, structured territory management, and data-informed sales execution. Success requires mastery of consultative selling, competitive awareness, and disciplined pipeline control. The role operates within a defined market strategy targeting underpenetrated fleet segments, contributing directly to revenue acceleration and market share expansion.

You will report directly to the VP and regularly collaborate with Fleet field sales teams.

Role Responsibilities

The responsibilities of the role will include :

• Prospecting Development : Prospecting, cold-calling, and generating new business opportunities within middle-market trucking / transportation accounts
• Sales Execution : Leading consulting sales conversations to uncover prospective goals, challenges, and needs. Presenting and demonstrating solutions that align with prospective needs and delivering clear value to their business.
• Early Life Cycle Management : Building genuine client rapport and managing client experience for the early life cycle of the account. Assist with onboarding, education and client transitions.
• Salesforce Proficiency : Navigating and utilizing Salesforce.com to track activities and manage customer interactions. Using internal CRM (or other systems) to accurately manage pipeline and forecasts.

Qualifications & Skills

The qualifications and skills required for this role include :

Benefits & Perks

The benefits and perks offered include :

Equal Opportunity / Affirmative Action Employer

Corpay is an Equal Opportunity Employer. Corpay provides equal employment opportunities to all employees and applicants without regard to race, color, gender (including pregnancy), religion, national origin, ancestry, disability, age, sexual orientation, gender identity or expression, marital status, language, ancestry, genetic information, veteran and / or military status or any other group status protected by federal or local law. If you require reasonable accommodation for the application and / or interview process, please notify a representative of the Human Resources Department.

Pay Transparency

This salary range is provided for locations which require such disclosure. Where a position or applicant may fall into a particular wage range depends on several factors including but not limited to skill sets, experience training licenses and certifications (if applicable), and other business and organizational needs. The disclosed range has not been adjusted for the applicable geographic markets. At Corpay it is not typical for an individual to be hired at or near the top of the range for their role and compensation decisions depend on the facts and circumstances of each case. The estimate of the minimum and maximum salary range is $65,000 with uncapped monthly commissions OTE $105,000.