Regional Sales Director

Company Description

Milestone Chassis keeps freight moving across America with one of the newest and best-equipped intermodal chassis fleets on the road. The company provides flexible chassis solutions for organizations of all sizes, ranging from same-day rentals to long-term leases and chassis pool access. Customers can rely on Milestone Chassis whether they need a single chassis or a fully managed nationwide fleet. The business is committed to reliability, scalability, and service, helping logistics and transportation partners operate efficiently and competitively.

This is a full-time, on-site Regional Sales Director role based in the Greater Chicago Area. The Regional Sales Director will lead sales efforts across an assigned territory, focusing on growing revenue through new business development and expanding relationships with existing customers. Day-to-day responsibilities include identifying and qualifying prospects, conducting client meetings and presentations, and developing tailored chassis and fleet solutions in collaboration with operations and sales support teams.

The role will oversee regional sales pipelines, forecast performance, and ensure accurate execution of contracts, pricing, and service agreements. The Regional Sales Director will also coach and mentor sales team members as needed, represent Milestone Chassis at industry events, and maintain a strong understanding of market trends, competitors, and customer needs in the intermodal and freight sectors.

• Proven experience in Sales and Business Development, with a track record of meeting or exceeding revenue targets in a B2B or logistics-focused environment.
• Background in Sales Operations, including pipeline management, forecasting, pricing, and contract oversight.
• Strong Customer Service orientation, with the ability to build long-term relationships and provide solutions-focused support to clients.
• Demonstrated Team Management skills, including coaching, performance feedback, and cross-functional collaboration.
• Excellent communication, negotiation, and presentation abilities, with strong analytical and problem-solving skills.
• Experience in transportation, intermodal, logistics, or related industries is strongly preferred.
• Bachelor’s degree in Business, Marketing, Logistics, or a related field, or equivalent combination of education and experience.
• Ability to travel within the regions as needed to meet with customers, partners, and internal teams.